TY  - JOUR
AU  - Taxeidis, George
AU  - Đapović, Milica
AU  - Nikolaivits, Efstratios
AU  - Maslak, Veselin
AU  - Nikodinović-Runić, Jasmina
AU  - Topakas, Evangelos
PY  - 2024
UR  - https://doi.org/10.1021/acssuschemeng.4c00143
UR  - https://imagine.imgge.bg.ac.rs/handle/123456789/2339
AB  - The discovery and engineering of novel biocatalysts capable of depolymerizing polyethylene terephthalate (PET) have gained significant attention since the need for green technologies to combat plastic pollution has become increasingly urgent. This study focuses on the development of novel substrates that can indicate enzymes with PET hydrolytic activity, streamlining the process of enzyme evaluation and selection. Four novel substrates, mimicking the structure of PET, were chemically synthesized and labeled with fluorogenic or chromogenic moieties, enabling the direct analysis of candidate enzymes without complex preparatory or analysis steps. The fluorogenic substrates, mUPET1, mUPET2, and mUPET3, not only identify enzymes capable of PET breakdown but also differentiate those with exceptional performance on the polymer, such as the benchmark PETase, LCCICCG. Among the substrates, the chromogenic p-NPhPET3 stands out as a reliable tool for screening both pure and crude enzymes, offering advantages over fluorogenic substrates such as ease of assay using UV–vis spectroscopy and compatibility with crude enzyme samples. However, ferulic acid esterases and mono-(2-hydroxyethyl) terephthalate esterases (MHETases), which exhibit remarkably high affinity for PET oligomers, also show high catalytic activity on these substrates. The substrates introduced in this study hold significant value in the function-based screening and characterization of enzymes that degrade PET, as well as the the potential to be used in screening mutant libraries derived from directed evolution experiments. Following this approach, a rapid and dependable assay method can be carried out using basic laboratory infrastructure, eliminating the necessity for intricate preparatory procedures before analysis.
PB  - American Chemical Society
T2  - ACS Sustainable Chemistry & Engineering
T1  - New Labeled PET Analogues Enable the Functional Screening and Characterization of PET-Degrading Enzymes
DO  - 10.1021/acssuschemeng.4c00143
ER  - 

@article{
author = "Taxeidis, George and Đapović, Milica and Nikolaivits, Efstratios and Maslak, Veselin and Nikodinović-Runić, Jasmina and Topakas, Evangelos",
year = "2024",
abstract = "The discovery and engineering of novel biocatalysts capable of depolymerizing polyethylene terephthalate (PET) have gained significant attention since the need for green technologies to combat plastic pollution has become increasingly urgent. This study focuses on the development of novel substrates that can indicate enzymes with PET hydrolytic activity, streamlining the process of enzyme evaluation and selection. Four novel substrates, mimicking the structure of PET, were chemically synthesized and labeled with fluorogenic or chromogenic moieties, enabling the direct analysis of candidate enzymes without complex preparatory or analysis steps. The fluorogenic substrates, mUPET1, mUPET2, and mUPET3, not only identify enzymes capable of PET breakdown but also differentiate those with exceptional performance on the polymer, such as the benchmark PETase, LCCICCG. Among the substrates, the chromogenic p-NPhPET3 stands out as a reliable tool for screening both pure and crude enzymes, offering advantages over fluorogenic substrates such as ease of assay using UV–vis spectroscopy and compatibility with crude enzyme samples. However, ferulic acid esterases and mono-(2-hydroxyethyl) terephthalate esterases (MHETases), which exhibit remarkably high affinity for PET oligomers, also show high catalytic activity on these substrates. The substrates introduced in this study hold significant value in the function-based screening and characterization of enzymes that degrade PET, as well as the the potential to be used in screening mutant libraries derived from directed evolution experiments. Following this approach, a rapid and dependable assay method can be carried out using basic laboratory infrastructure, eliminating the necessity for intricate preparatory procedures before analysis.",
publisher = "American Chemical Society",
journal = "ACS Sustainable Chemistry & Engineering",
title = "New Labeled PET Analogues Enable the Functional Screening and Characterization of PET-Degrading Enzymes",
doi = "10.1021/acssuschemeng.4c00143"
}

Taxeidis, G., Đapović, M., Nikolaivits, E., Maslak, V., Nikodinović-Runić, J.,& Topakas, E.. (2024). New Labeled PET Analogues Enable the Functional Screening and Characterization of PET-Degrading Enzymes. in ACS Sustainable Chemistry & Engineering
American Chemical Society..
https://doi.org/10.1021/acssuschemeng.4c00143

Taxeidis G, Đapović M, Nikolaivits E, Maslak V, Nikodinović-Runić J, Topakas E. New Labeled PET Analogues Enable the Functional Screening and Characterization of PET-Degrading Enzymes. in ACS Sustainable Chemistry & Engineering. 2024;.
doi:10.1021/acssuschemeng.4c00143 .

Taxeidis, George, Đapović, Milica, Nikolaivits, Efstratios, Maslak, Veselin, Nikodinović-Runić, Jasmina, Topakas, Evangelos, "New Labeled PET Analogues Enable the Functional Screening and Characterization of PET-Degrading Enzymes" in ACS Sustainable Chemistry & Engineering (2024),
https://doi.org/10.1021/acssuschemeng.4c00143 . .

TY  - JOUR
AU  - Mitrović, Aleksandra
AU  - Milovanović, Jelena
AU  - Gurgul, Jacek
AU  - Žekić, Andrijana
AU  - Nikodinović-Runić, Jasmina
AU  - Maslak, Veselin
PY  - 2023
UR  - https://www.sciencedirect.com/science/article/pii/S0141022923001011
UR  - https://imagine.imgge.bg.ac.rs/handle/123456789/1984
AB  - We present a novel approach for the enzymatic functionalization of graphene, utilizing horseradish peroxidase (HPO) and laccase (LC) from Trametes versicolor. This study demonstrates, for the first time, the covalent modification of non-homogeneous graphene with a low surface-to-volume ratio, both in solution and on solid support. Through thermogravimetry analysis, we estimate the degree of functionalization to be 11% with HPO and 4% with LC, attributed to the varying redox potentials of the enzymes. This work highlights the potential of enzymatic reactions for tailored functionalization of graphene under mild conditions.
PB  - Elsevier
T2  - Enzyme and Microbial Technology
T1  - Enzymatic functionalization of liquid phase exfoliated graphene using horseradish peroxidase and laccase
SP  - 110293
VL  - 170
DO  - 10.1016/j.enzmictec.2023.110293
ER  - 

@article{
author = "Mitrović, Aleksandra and Milovanović, Jelena and Gurgul, Jacek and Žekić, Andrijana and Nikodinović-Runić, Jasmina and Maslak, Veselin",
year = "2023",
abstract = "We present a novel approach for the enzymatic functionalization of graphene, utilizing horseradish peroxidase (HPO) and laccase (LC) from Trametes versicolor. This study demonstrates, for the first time, the covalent modification of non-homogeneous graphene with a low surface-to-volume ratio, both in solution and on solid support. Through thermogravimetry analysis, we estimate the degree of functionalization to be 11% with HPO and 4% with LC, attributed to the varying redox potentials of the enzymes. This work highlights the potential of enzymatic reactions for tailored functionalization of graphene under mild conditions.",
publisher = "Elsevier",
journal = "Enzyme and Microbial Technology",
title = "Enzymatic functionalization of liquid phase exfoliated graphene using horseradish peroxidase and laccase",
pages = "110293",
volume = "170",
doi = "10.1016/j.enzmictec.2023.110293"
}

Mitrović, A., Milovanović, J., Gurgul, J., Žekić, A., Nikodinović-Runić, J.,& Maslak, V.. (2023). Enzymatic functionalization of liquid phase exfoliated graphene using horseradish peroxidase and laccase. in Enzyme and Microbial Technology
Elsevier., 170, 110293.
https://doi.org/10.1016/j.enzmictec.2023.110293

Mitrović A, Milovanović J, Gurgul J, Žekić A, Nikodinović-Runić J, Maslak V. Enzymatic functionalization of liquid phase exfoliated graphene using horseradish peroxidase and laccase. in Enzyme and Microbial Technology. 2023;170:110293.
doi:10.1016/j.enzmictec.2023.110293 .

Mitrović, Aleksandra, Milovanović, Jelena, Gurgul, Jacek, Žekić, Andrijana, Nikodinović-Runić, Jasmina, Maslak, Veselin, "Enzymatic functionalization of liquid phase exfoliated graphene using horseradish peroxidase and laccase" in Enzyme and Microbial Technology, 170 (2023):110293,
https://doi.org/10.1016/j.enzmictec.2023.110293 . .

TY  - CONF
AU  - Nenadović, Marija
AU  - Pantelić, Brana
AU  - Lazić, Jelena
AU  - Maslak, Veselin
AU  - Nikodinović-Runić, Jasmina
AU  - Milovanović, Jelena
PY  - 2023
UR  - https://afea.eventsair.com/10th-conference-of-mikrobiokosmos/abstract-book
UR  - https://imagine.imgge.bg.ac.rs/handle/123456789/2237
AB  - PHAs are naturally made microbial polyesters that
have been commercialized as biodegradable
plastics. However, it has been shown that these
materials are not so easily biodegraded in natural
environments [1]. PHA depolymerases are key PHA
degrading enzymes and their identification and
characterization is of great interest and importance.
Currently, screening is done on polymeric
substrates using techniques such as clear zone
assays on agar or weight loss measurements.
Results obtained using these different methods
cannot be directly compared, since they depend
highly on the polymer used, PHA granules
preparation and assay conditions [2].
In order to design a more specific test for the
determination of PHA depolymerase activity, we
synthesized 3-hyoxyalkanoate monomers (3-HA
monomer) and 3-hyoxyalkanoic acid dimers (3-HA
dimer) and their respective p-nitrophenyl esters,
allowing for spectrophotometric determination of
their activity [3]. Compounds were characterized
using N and FTIR. Para-nitrophenyl labeled
substrates were then used in the enzymatic activity
assay with the benchmark polyhyoxyoctanoate
(PHO) depolymerase from Pseudomonas
fluorescens GK13 expressed in Escherichia coli
CodonPlus-RIPL hosts. This activity was compared
to recombinantly expressed leaf-branch compost
cutinase (LCC cutinase) and
polyethyleneterephtalate (PET) hyolyzing esterase
from Ideonella sakaiensis (IsPETase). Our initial
results revealed increased specificity of PHO
depolymerase towards newly synthetized
substrates, suggesting their suitability for specific
screens and isolation of new mcl-PHA
depolymerases, as well as in high throughput
screening assays designed for guiding their
directed evolution.
C3  - 10th Conference of Mikrobiokosmos
T1  - Medium chain length polyhyoxyalkanoates (mcl-PHA) model compounds for the discovery of novel PHA depolymerases
UR  - https://hdl.handle.net/21.15107/rcub_imagine_2237
ER  - 

@conference{
author = "Nenadović, Marija and Pantelić, Brana and Lazić, Jelena and Maslak, Veselin and Nikodinović-Runić, Jasmina and Milovanović, Jelena",
year = "2023",
abstract = "PHAs are naturally made microbial polyesters that
have been commercialized as biodegradable
plastics. However, it has been shown that these
materials are not so easily biodegraded in natural
environments [1]. PHA depolymerases are key PHA
degrading enzymes and their identification and
characterization is of great interest and importance.
Currently, screening is done on polymeric
substrates using techniques such as clear zone
assays on agar or weight loss measurements.
Results obtained using these different methods
cannot be directly compared, since they depend
highly on the polymer used, PHA granules
preparation and assay conditions [2].
In order to design a more specific test for the
determination of PHA depolymerase activity, we
synthesized 3-hyoxyalkanoate monomers (3-HA
monomer) and 3-hyoxyalkanoic acid dimers (3-HA
dimer) and their respective p-nitrophenyl esters,
allowing for spectrophotometric determination of
their activity [3]. Compounds were characterized
using N and FTIR. Para-nitrophenyl labeled
substrates were then used in the enzymatic activity
assay with the benchmark polyhyoxyoctanoate
(PHO) depolymerase from Pseudomonas
fluorescens GK13 expressed in Escherichia coli
CodonPlus-RIPL hosts. This activity was compared
to recombinantly expressed leaf-branch compost
cutinase (LCC cutinase) and
polyethyleneterephtalate (PET) hyolyzing esterase
from Ideonella sakaiensis (IsPETase). Our initial
results revealed increased specificity of PHO
depolymerase towards newly synthetized
substrates, suggesting their suitability for specific
screens and isolation of new mcl-PHA
depolymerases, as well as in high throughput
screening assays designed for guiding their
directed evolution.",
journal = "10th Conference of Mikrobiokosmos",
title = "Medium chain length polyhyoxyalkanoates (mcl-PHA) model compounds for the discovery of novel PHA depolymerases",
url = "https://hdl.handle.net/21.15107/rcub_imagine_2237"
}

Nenadović, M., Pantelić, B., Lazić, J., Maslak, V., Nikodinović-Runić, J.,& Milovanović, J.. (2023). Medium chain length polyhyoxyalkanoates (mcl-PHA) model compounds for the discovery of novel PHA depolymerases. in 10th Conference of Mikrobiokosmos.
https://hdl.handle.net/21.15107/rcub_imagine_2237

Nenadović M, Pantelić B, Lazić J, Maslak V, Nikodinović-Runić J, Milovanović J. Medium chain length polyhyoxyalkanoates (mcl-PHA) model compounds for the discovery of novel PHA depolymerases. in 10th Conference of Mikrobiokosmos. 2023;.
https://hdl.handle.net/21.15107/rcub_imagine_2237 .

Nenadović, Marija, Pantelić, Brana, Lazić, Jelena, Maslak, Veselin, Nikodinović-Runić, Jasmina, Milovanović, Jelena, "Medium chain length polyhyoxyalkanoates (mcl-PHA) model compounds for the discovery of novel PHA depolymerases" in 10th Conference of Mikrobiokosmos (2023),
https://hdl.handle.net/21.15107/rcub_imagine_2237 .

TY  - JOUR
AU  - Pantelić, Brana
AU  - Škaro Bogojević, Sanja
AU  - Milivojević, Dušan
AU  - Ilić-Tomić, Tatjana
AU  - Lončarević, Branka
AU  - Beskoski, Vladimir
AU  - Maslak, Veselin
AU  - Guzik, Maciej
AU  - Makryniotis, Konstantinos
AU  - Taxeidis, George
AU  - Siaperas, Romanos
AU  - Topakas, Evangelos
AU  - Nikodinović-Runić, Jasmina
PY  - 2023
UR  - https://www.mdpi.com/2073-4344/13/2/278
UR  - https://imagine.imgge.bg.ac.rs/handle/123456789/1790
AB  - Polyurethanes (PUs) are an exceedingly heterogeneous group of plastic polymers, widely used in a variety of industries from construction to medical implants. In the past decades, we have witnessed the accumulation of PU waste and its detrimental environmental impacts. PUs have been identified as one of the most toxic polymers leaching hazardous compounds derived both from the polymer itself and the additives used in production. Further environmental impact assessment, identification and characterization of substances derived from PU materials and establishing efficient degradation strategies are crucial. Thus, a selection of eight synthetic model compounds which represent partial PU hydrolysis products were synthesized and characterized both in terms of toxicity and suitability to be used as substrates for the identification of novel biocatalysts for PU biodegradation. Overall, the compounds exhibited low in vitro cytotoxicity against a healthy human fibroblast cell line and virtually no toxic effect on the nematode Caenorhabditis elegans up to 500 µg mL−1, and two of the substrates showed moderate aquatic ecotoxicity with EC50 values 53 µg mL−1 and 45 µg mL−1, respectively, on Aliivibrio fischeri. The compounds were successfully applied to study the mechanism of ester and urethane bond cleaving preference of known plastic-degrading enzymes and were used to single out a novel PU-degrading biocatalyst, Amycolatopsis mediterranei ISP5501, among 220 microbial strains. A. mediterranei ISP5501 can also degrade commercially available polyether and polyester PU materials, reducing the average molecular number of the polymer up to 13.5%. This study uncovered a biocatalyst capable of degrading different types of PUs and identified potential enzymes responsible as a key step in developing biotechnological process for PU waste treatment options.
T2  - Catalysts
T2  - Catalysts
T1  - Set of Small Molecule Polyurethane (PU) Model Substrates: Ecotoxicity Evaluation and Identification of PU Degrading Biocatalysts
IS  - 2
SP  - 278
VL  - 13
DO  - 10.3390/catal13020278
ER  - 

@article{
author = "Pantelić, Brana and Škaro Bogojević, Sanja and Milivojević, Dušan and Ilić-Tomić, Tatjana and Lončarević, Branka and Beskoski, Vladimir and Maslak, Veselin and Guzik, Maciej and Makryniotis, Konstantinos and Taxeidis, George and Siaperas, Romanos and Topakas, Evangelos and Nikodinović-Runić, Jasmina",
year = "2023",
abstract = "Polyurethanes (PUs) are an exceedingly heterogeneous group of plastic polymers, widely used in a variety of industries from construction to medical implants. In the past decades, we have witnessed the accumulation of PU waste and its detrimental environmental impacts. PUs have been identified as one of the most toxic polymers leaching hazardous compounds derived both from the polymer itself and the additives used in production. Further environmental impact assessment, identification and characterization of substances derived from PU materials and establishing efficient degradation strategies are crucial. Thus, a selection of eight synthetic model compounds which represent partial PU hydrolysis products were synthesized and characterized both in terms of toxicity and suitability to be used as substrates for the identification of novel biocatalysts for PU biodegradation. Overall, the compounds exhibited low in vitro cytotoxicity against a healthy human fibroblast cell line and virtually no toxic effect on the nematode Caenorhabditis elegans up to 500 µg mL−1, and two of the substrates showed moderate aquatic ecotoxicity with EC50 values 53 µg mL−1 and 45 µg mL−1, respectively, on Aliivibrio fischeri. The compounds were successfully applied to study the mechanism of ester and urethane bond cleaving preference of known plastic-degrading enzymes and were used to single out a novel PU-degrading biocatalyst, Amycolatopsis mediterranei ISP5501, among 220 microbial strains. A. mediterranei ISP5501 can also degrade commercially available polyether and polyester PU materials, reducing the average molecular number of the polymer up to 13.5%. This study uncovered a biocatalyst capable of degrading different types of PUs and identified potential enzymes responsible as a key step in developing biotechnological process for PU waste treatment options.",
journal = "Catalysts, Catalysts",
title = "Set of Small Molecule Polyurethane (PU) Model Substrates: Ecotoxicity Evaluation and Identification of PU Degrading Biocatalysts",
number = "2",
pages = "278",
volume = "13",
doi = "10.3390/catal13020278"
}

Pantelić, B., Škaro Bogojević, S., Milivojević, D., Ilić-Tomić, T., Lončarević, B., Beskoski, V., Maslak, V., Guzik, M., Makryniotis, K., Taxeidis, G., Siaperas, R., Topakas, E.,& Nikodinović-Runić, J.. (2023). Set of Small Molecule Polyurethane (PU) Model Substrates: Ecotoxicity Evaluation and Identification of PU Degrading Biocatalysts. in Catalysts, 13(2), 278.
https://doi.org/10.3390/catal13020278

Pantelić B, Škaro Bogojević S, Milivojević D, Ilić-Tomić T, Lončarević B, Beskoski V, Maslak V, Guzik M, Makryniotis K, Taxeidis G, Siaperas R, Topakas E, Nikodinović-Runić J. Set of Small Molecule Polyurethane (PU) Model Substrates: Ecotoxicity Evaluation and Identification of PU Degrading Biocatalysts. in Catalysts. 2023;13(2):278.
doi:10.3390/catal13020278 .

Pantelić, Brana, Škaro Bogojević, Sanja, Milivojević, Dušan, Ilić-Tomić, Tatjana, Lončarević, Branka, Beskoski, Vladimir, Maslak, Veselin, Guzik, Maciej, Makryniotis, Konstantinos, Taxeidis, George, Siaperas, Romanos, Topakas, Evangelos, Nikodinović-Runić, Jasmina, "Set of Small Molecule Polyurethane (PU) Model Substrates: Ecotoxicity Evaluation and Identification of PU Degrading Biocatalysts" in Catalysts, 13, no. 2 (2023):278,
https://doi.org/10.3390/catal13020278 . .

TY  - JOUR
AU  - Nikolaivits, Efstratios
AU  - Taxeidis, George
AU  - Gkountela, Christina
AU  - Vouyiouka, Stamatina
AU  - Maslak, Veselin
AU  - Nikodinović-Runić, Jasmina
AU  - Topakas, Evangelos
PY  - 2022
UR  - https://imagine.imgge.bg.ac.rs/handle/123456789/1630
AB  - The uncontrolled release of plastics in the environment has rendered them ubiquitous around the planet, threatening the wildlife and human health. Biodegradation and valorization of plastics has emerged as an ecofriendly alternative to conventional management techniques. Discovery of novel polymer-degrading enzymes with diversified properties is hence an important task in order to explore different operational conditions for plastic-waste upcycling. In the present study, a barely studied psychrophilic enzyme (MoPE) from the Antractic bacterium Moraxella sp. was heterologously expressed, characterized and its potential in polymer degradation was further investigated. Based on its amino acid composition and structure, MoPE resembled PET-degrading enzymes, sharing features from both mesophilic and thermophilic homologues. MoPE hydrolyzes nonbiodegradable plastics, such as polyethylene terephthalate and polyurethane, as well as biodegradable
PB  - Elsevier, Amsterdam
T2  - Journal of Hazardous Materials
T1  - A polyesterase from the Antarctic bacterium Moraxella sp. degrades highly crystalline synthetic polymers
VL  - 434
DO  - 10.1016/j.jhazmat.2022.128900
ER  - 

@article{
author = "Nikolaivits, Efstratios and Taxeidis, George and Gkountela, Christina and Vouyiouka, Stamatina and Maslak, Veselin and Nikodinović-Runić, Jasmina and Topakas, Evangelos",
year = "2022",
abstract = "The uncontrolled release of plastics in the environment has rendered them ubiquitous around the planet, threatening the wildlife and human health. Biodegradation and valorization of plastics has emerged as an ecofriendly alternative to conventional management techniques. Discovery of novel polymer-degrading enzymes with diversified properties is hence an important task in order to explore different operational conditions for plastic-waste upcycling. In the present study, a barely studied psychrophilic enzyme (MoPE) from the Antractic bacterium Moraxella sp. was heterologously expressed, characterized and its potential in polymer degradation was further investigated. Based on its amino acid composition and structure, MoPE resembled PET-degrading enzymes, sharing features from both mesophilic and thermophilic homologues. MoPE hydrolyzes nonbiodegradable plastics, such as polyethylene terephthalate and polyurethane, as well as biodegradable",
publisher = "Elsevier, Amsterdam",
journal = "Journal of Hazardous Materials",
title = "A polyesterase from the Antarctic bacterium Moraxella sp. degrades highly crystalline synthetic polymers",
volume = "434",
doi = "10.1016/j.jhazmat.2022.128900"
}

Nikolaivits, E., Taxeidis, G., Gkountela, C., Vouyiouka, S., Maslak, V., Nikodinović-Runić, J.,& Topakas, E.. (2022). A polyesterase from the Antarctic bacterium Moraxella sp. degrades highly crystalline synthetic polymers. in Journal of Hazardous Materials
Elsevier, Amsterdam., 434.
https://doi.org/10.1016/j.jhazmat.2022.128900

Nikolaivits E, Taxeidis G, Gkountela C, Vouyiouka S, Maslak V, Nikodinović-Runić J, Topakas E. A polyesterase from the Antarctic bacterium Moraxella sp. degrades highly crystalline synthetic polymers. in Journal of Hazardous Materials. 2022;434.
doi:10.1016/j.jhazmat.2022.128900 .

Nikolaivits, Efstratios, Taxeidis, George, Gkountela, Christina, Vouyiouka, Stamatina, Maslak, Veselin, Nikodinović-Runić, Jasmina, Topakas, Evangelos, "A polyesterase from the Antarctic bacterium Moraxella sp. degrades highly crystalline synthetic polymers" in Journal of Hazardous Materials, 434 (2022),
https://doi.org/10.1016/j.jhazmat.2022.128900 . .

TY  - JOUR
AU  - Đapović, Milica
AU  - Milivojević, Dušan
AU  - Ilić-Tomić, Tatjana
AU  - Lješević, Marija
AU  - Nikolaivits, Efstratios
AU  - Topakas, Evangelos
AU  - Maslak, Veselin
AU  - Nikodinović-Runić, Jasmina
PY  - 2021
UR  - https://www.sciencedirect.com/science/article/pii/S0045653521004744
UR  - https://imagine.imgge.bg.ac.rs/handle/123456789/1732
AB  - Polyethylene terephthalate (PET) is widely used material and as such became highly enriched in nature. It is generally considered inert and safe plastic, but due to the recent increased efforts to break-down PET using biotechnological approaches, we realized the scarcity of information about structural analysis of possible degradation products and their ecotoxicological assessment. Therefore, in this study, 11 compounds belonging to the group of PET precursors and possible degradation products have been comprehensively characterized. Seven of these compounds including 1-(2-hydroxyethyl)-4-methylterephthalate, ethylene glycol bis(methyl terephthalate), methyl bis(2-hydroxyethyl terephtahalate), 1,4-benzenedicarboxylic acid, 1,4-bis[2-[[4-(methoxycarbonyl)benzoyl]oxy]ethyl] ester and methyl tris(2-hydroxyethyl terephthalate) corresponding to mono-, 1.5-, di-, 2,5- and trimer of PET were synthetized and structurally characterized for the first time. In-silico druglikeness and physico-chemical properties of these compounds were predicted using variety of platforms. No antimicrobial properties were detected even at 1000 μg/mL. Ecotoxicological impact of the compounds against marine bacteria Allivibrio fischeri proved that the 6 out of 11 tested PET-associated compounds may be classified as harmful to aquatic microorganisms, with PET trimer being one of the most toxic. In comparison, most of the compounds were not toxic on human lung fibroblasts (MRC-5) at 200 μg/mL with inhibiting concentration (IC50) values of 30 μg/mL and 50 μg/mL determined for PET dimer and trimer. Only three of these compounds including PET monomer were toxic to nematode Caenorhabditis elegans at high concentration of 500 μg/mL. In terms of the applicative potential, PET dimer can be used as suitable substrate for the screening, identification and characterization of novel PET-depolymerizing enzymes.
PB  - Elsevier
T2  - Chemosphere
T2  - ChemosphereChemosphere
T1  - Synthesis and characterization of polyethylene terephthalate (PET) precursors and potential degradation products: Toxicity study and application in discovery of novel PETases
SP  - 130005
VL  - 275
DO  - 10.1016/j.chemosphere.2021.130005
ER  - 

@article{
author = "Đapović, Milica and Milivojević, Dušan and Ilić-Tomić, Tatjana and Lješević, Marija and Nikolaivits, Efstratios and Topakas, Evangelos and Maslak, Veselin and Nikodinović-Runić, Jasmina",
year = "2021",
abstract = "Polyethylene terephthalate (PET) is widely used material and as such became highly enriched in nature. It is generally considered inert and safe plastic, but due to the recent increased efforts to break-down PET using biotechnological approaches, we realized the scarcity of information about structural analysis of possible degradation products and their ecotoxicological assessment. Therefore, in this study, 11 compounds belonging to the group of PET precursors and possible degradation products have been comprehensively characterized. Seven of these compounds including 1-(2-hydroxyethyl)-4-methylterephthalate, ethylene glycol bis(methyl terephthalate), methyl bis(2-hydroxyethyl terephtahalate), 1,4-benzenedicarboxylic acid, 1,4-bis[2-[[4-(methoxycarbonyl)benzoyl]oxy]ethyl] ester and methyl tris(2-hydroxyethyl terephthalate) corresponding to mono-, 1.5-, di-, 2,5- and trimer of PET were synthetized and structurally characterized for the first time. In-silico druglikeness and physico-chemical properties of these compounds were predicted using variety of platforms. No antimicrobial properties were detected even at 1000 μg/mL. Ecotoxicological impact of the compounds against marine bacteria Allivibrio fischeri proved that the 6 out of 11 tested PET-associated compounds may be classified as harmful to aquatic microorganisms, with PET trimer being one of the most toxic. In comparison, most of the compounds were not toxic on human lung fibroblasts (MRC-5) at 200 μg/mL with inhibiting concentration (IC50) values of 30 μg/mL and 50 μg/mL determined for PET dimer and trimer. Only three of these compounds including PET monomer were toxic to nematode Caenorhabditis elegans at high concentration of 500 μg/mL. In terms of the applicative potential, PET dimer can be used as suitable substrate for the screening, identification and characterization of novel PET-depolymerizing enzymes.",
publisher = "Elsevier",
journal = "Chemosphere, ChemosphereChemosphere",
title = "Synthesis and characterization of polyethylene terephthalate (PET) precursors and potential degradation products: Toxicity study and application in discovery of novel PETases",
pages = "130005",
volume = "275",
doi = "10.1016/j.chemosphere.2021.130005"
}

Đapović, M., Milivojević, D., Ilić-Tomić, T., Lješević, M., Nikolaivits, E., Topakas, E., Maslak, V.,& Nikodinović-Runić, J.. (2021). Synthesis and characterization of polyethylene terephthalate (PET) precursors and potential degradation products: Toxicity study and application in discovery of novel PETases. in Chemosphere
Elsevier., 275, 130005.
https://doi.org/10.1016/j.chemosphere.2021.130005

Đapović M, Milivojević D, Ilić-Tomić T, Lješević M, Nikolaivits E, Topakas E, Maslak V, Nikodinović-Runić J. Synthesis and characterization of polyethylene terephthalate (PET) precursors and potential degradation products: Toxicity study and application in discovery of novel PETases. in Chemosphere. 2021;275:130005.
doi:10.1016/j.chemosphere.2021.130005 .

Đapović, Milica, Milivojević, Dušan, Ilić-Tomić, Tatjana, Lješević, Marija, Nikolaivits, Efstratios, Topakas, Evangelos, Maslak, Veselin, Nikodinović-Runić, Jasmina, "Synthesis and characterization of polyethylene terephthalate (PET) precursors and potential degradation products: Toxicity study and application in discovery of novel PETases" in Chemosphere, 275 (2021):130005,
https://doi.org/10.1016/j.chemosphere.2021.130005 . .

TY  - JOUR
AU  - Nikolaivits, Efstratios
AU  - Dimopoulou, Phaedra
AU  - Maslak, Veselin
AU  - Nikodinović-Runić, Jasmina
AU  - Topakas, Evangelos
PY  - 2020
UR  - https://imagine.imgge.bg.ac.rs/handle/123456789/1633
AB  - Plastic waste poses an enormous environmental problem as a result of soil and ocean contamination, causing the release of microplastics that end up in humans through the food web. Enzymatic degradation of plastics has emerged as an alternative to traditional recycling processes. In the present work, we used bioinfomatics tools to discover a gene coding for a putative polyester degrading enzyme (polyesterase). The gene was heterologously expressed, purified and biochemically characterized. Furthermore, its ability to degrade polyethylene terephthalate (PET) model substrates and synthetic plastics was assessed.
T2  - Chemistry Proceedings
T2  - Chemistry Proceedings
T1  - Discovery and Biochemical Characterization of a Novel Polyesterase for the Degradation of Synthetic Plastics
IS  - 1
SP  - 33
VL  - 2
DO  - 10.3390/ECCS2020-07572
ER  - 

@article{
author = "Nikolaivits, Efstratios and Dimopoulou, Phaedra and Maslak, Veselin and Nikodinović-Runić, Jasmina and Topakas, Evangelos",
year = "2020",
abstract = "Plastic waste poses an enormous environmental problem as a result of soil and ocean contamination, causing the release of microplastics that end up in humans through the food web. Enzymatic degradation of plastics has emerged as an alternative to traditional recycling processes. In the present work, we used bioinfomatics tools to discover a gene coding for a putative polyester degrading enzyme (polyesterase). The gene was heterologously expressed, purified and biochemically characterized. Furthermore, its ability to degrade polyethylene terephthalate (PET) model substrates and synthetic plastics was assessed.",
journal = "Chemistry Proceedings, Chemistry Proceedings",
title = "Discovery and Biochemical Characterization of a Novel Polyesterase for the Degradation of Synthetic Plastics",
number = "1",
pages = "33",
volume = "2",
doi = "10.3390/ECCS2020-07572"
}

Nikolaivits, E., Dimopoulou, P., Maslak, V., Nikodinović-Runić, J.,& Topakas, E.. (2020). Discovery and Biochemical Characterization of a Novel Polyesterase for the Degradation of Synthetic Plastics. in Chemistry Proceedings, 2(1), 33.
https://doi.org/10.3390/ECCS2020-07572

Nikolaivits E, Dimopoulou P, Maslak V, Nikodinović-Runić J, Topakas E. Discovery and Biochemical Characterization of a Novel Polyesterase for the Degradation of Synthetic Plastics. in Chemistry Proceedings. 2020;2(1):33.
doi:10.3390/ECCS2020-07572 .

Nikolaivits, Efstratios, Dimopoulou, Phaedra, Maslak, Veselin, Nikodinović-Runić, Jasmina, Topakas, Evangelos, "Discovery and Biochemical Characterization of a Novel Polyesterase for the Degradation of Synthetic Plastics" in Chemistry Proceedings, 2, no. 1 (2020):33,
https://doi.org/10.3390/ECCS2020-07572 . .

TY  - JOUR
AU  - Jaksić, Jovana
AU  - Ostojić, Sanja
AU  - Micić, Darko
AU  - Vujosević, Zorana Tokic
AU  - Milovanović, Jelena
AU  - Karkalić, Radovan
AU  - O'Connor, Kevin
AU  - Kenny, Shane T.
AU  - Casey, William
AU  - Nikodinović-Runić, Jasmina
AU  - Maslak, Veselin
PY  - 2020
UR  - https://imagine.imgge.bg.ac.rs/handle/123456789/1399
AB  - In the present work, we describe the chemical synthesis of 3-HFAs as prominent derivatives of fatty acids and assess if they could be applied as phase change materials (PCM). In addition, 3-HFAs were obtained by depolymerization of a bacterial biopolymeric material, polyhydroxyalkanoate. Thermal properties of 3-hydoxyoctanoic, decanoic, and dodecanoic acids are reported for the first time. These materials showed the potential to be applied as PCM in temperature range from 33 degrees C to 66 degrees C. In order to expand the temperature range for application of 3-HFAs as PCM, eutectic mass ratios of three kinds of binary mixtures of 3-HFAs were calculated, and their properties were predicted using the Schroder-van Laar equation. Thermal properties of these mixtures were validated by differential scanning calorimetry (DSC) analysis. These results showed that eutectics considerably expanded the scope of applications of 3-HFAs as PCMs. 3-HFAs originating from biotechnologically obtained polyhydroxyalkanoates also showed potential to be applied in development of PCMs.
PB  - Hoboken : Wiley
T2  - International Journal of Energy Research
T1  - Thermal properties of 3-hydroxy fatty acids and their binary mixtures as phase change energy storage materials
EP  - 1302
IS  - 2
SP  - 1294
VL  - 44
DO  - 10.1002/er.4934
ER  - 

@article{
author = "Jaksić, Jovana and Ostojić, Sanja and Micić, Darko and Vujosević, Zorana Tokic and Milovanović, Jelena and Karkalić, Radovan and O'Connor, Kevin and Kenny, Shane T. and Casey, William and Nikodinović-Runić, Jasmina and Maslak, Veselin",
year = "2020",
abstract = "In the present work, we describe the chemical synthesis of 3-HFAs as prominent derivatives of fatty acids and assess if they could be applied as phase change materials (PCM). In addition, 3-HFAs were obtained by depolymerization of a bacterial biopolymeric material, polyhydroxyalkanoate. Thermal properties of 3-hydoxyoctanoic, decanoic, and dodecanoic acids are reported for the first time. These materials showed the potential to be applied as PCM in temperature range from 33 degrees C to 66 degrees C. In order to expand the temperature range for application of 3-HFAs as PCM, eutectic mass ratios of three kinds of binary mixtures of 3-HFAs were calculated, and their properties were predicted using the Schroder-van Laar equation. Thermal properties of these mixtures were validated by differential scanning calorimetry (DSC) analysis. These results showed that eutectics considerably expanded the scope of applications of 3-HFAs as PCMs. 3-HFAs originating from biotechnologically obtained polyhydroxyalkanoates also showed potential to be applied in development of PCMs.",
publisher = "Hoboken : Wiley",
journal = "International Journal of Energy Research",
title = "Thermal properties of 3-hydroxy fatty acids and their binary mixtures as phase change energy storage materials",
pages = "1302-1294",
number = "2",
volume = "44",
doi = "10.1002/er.4934"
}

Jaksić, J., Ostojić, S., Micić, D., Vujosević, Z. T., Milovanović, J., Karkalić, R., O'Connor, K., Kenny, S. T., Casey, W., Nikodinović-Runić, J.,& Maslak, V.. (2020). Thermal properties of 3-hydroxy fatty acids and their binary mixtures as phase change energy storage materials. in International Journal of Energy Research
Hoboken : Wiley., 44(2), 1294-1302.
https://doi.org/10.1002/er.4934

Jaksić J, Ostojić S, Micić D, Vujosević ZT, Milovanović J, Karkalić R, O'Connor K, Kenny ST, Casey W, Nikodinović-Runić J, Maslak V. Thermal properties of 3-hydroxy fatty acids and their binary mixtures as phase change energy storage materials. in International Journal of Energy Research. 2020;44(2):1294-1302.
doi:10.1002/er.4934 .

Jaksić, Jovana, Ostojić, Sanja, Micić, Darko, Vujosević, Zorana Tokic, Milovanović, Jelena, Karkalić, Radovan, O'Connor, Kevin, Kenny, Shane T., Casey, William, Nikodinović-Runić, Jasmina, Maslak, Veselin, "Thermal properties of 3-hydroxy fatty acids and their binary mixtures as phase change energy storage materials" in International Journal of Energy Research, 44, no. 2 (2020):1294-1302,
https://doi.org/10.1002/er.4934 . .

TY  - JOUR
AU  - Xie, Yun
AU  - Ilić, Stefan
AU  - Škaro Bogojević, Sanja
AU  - Maslak, Veselin
AU  - Glusac, Ksenija D.
PY  - 2017
UR  - https://imagine.imgge.bg.ac.rs/handle/123456789/998
AB  - The excited-state heterolysis of acridinol-based derivatives leads to the release of the OH- ion and the formation of the corresponding acridinium cations. To evaluate the parameters that control the reaction barriers, the kinetics of excited-state OH- release from a series of acridinol photobases were studied using transient absorption spectroscopy. The rate constants were obtained in three solvents (methanol, butanol, and isobutanol), and the data were modeled using Marcus theory. The intrinsic reorganization energies obtained from these fits were found to correlate well with the solvent reorganization energies calculated using dielectric continuum model, suggesting that the excited-state OH- release occurs along the solvent reaction coordinate. Furthermore, the ability of acridinol photobases to photoinitiate chemical reactions was demonstrated using the Michael reaction between dimethylmalonate and nitrostyrene.
PB  - Amer Chemical Soc, Washington
T2  - Journal of Physical Chemistry A
T1  - Excited-State Hydroxide Ion Release From a Series of Acridinol Photobases
EP  - 457
IS  - 2
SP  - 448
VL  - 121
DO  - 10.1021/acs.jpca.6b10980
ER  - 

@article{
author = "Xie, Yun and Ilić, Stefan and Škaro Bogojević, Sanja and Maslak, Veselin and Glusac, Ksenija D.",
year = "2017",
abstract = "The excited-state heterolysis of acridinol-based derivatives leads to the release of the OH- ion and the formation of the corresponding acridinium cations. To evaluate the parameters that control the reaction barriers, the kinetics of excited-state OH- release from a series of acridinol photobases were studied using transient absorption spectroscopy. The rate constants were obtained in three solvents (methanol, butanol, and isobutanol), and the data were modeled using Marcus theory. The intrinsic reorganization energies obtained from these fits were found to correlate well with the solvent reorganization energies calculated using dielectric continuum model, suggesting that the excited-state OH- release occurs along the solvent reaction coordinate. Furthermore, the ability of acridinol photobases to photoinitiate chemical reactions was demonstrated using the Michael reaction between dimethylmalonate and nitrostyrene.",
publisher = "Amer Chemical Soc, Washington",
journal = "Journal of Physical Chemistry A",
title = "Excited-State Hydroxide Ion Release From a Series of Acridinol Photobases",
pages = "457-448",
number = "2",
volume = "121",
doi = "10.1021/acs.jpca.6b10980"
}

Xie, Y., Ilić, S., Škaro Bogojević, S., Maslak, V.,& Glusac, K. D.. (2017). Excited-State Hydroxide Ion Release From a Series of Acridinol Photobases. in Journal of Physical Chemistry A
Amer Chemical Soc, Washington., 121(2), 448-457.
https://doi.org/10.1021/acs.jpca.6b10980

Xie Y, Ilić S, Škaro Bogojević S, Maslak V, Glusac KD. Excited-State Hydroxide Ion Release From a Series of Acridinol Photobases. in Journal of Physical Chemistry A. 2017;121(2):448-457.
doi:10.1021/acs.jpca.6b10980 .

Xie, Yun, Ilić, Stefan, Škaro Bogojević, Sanja, Maslak, Veselin, Glusac, Ksenija D., "Excited-State Hydroxide Ion Release From a Series of Acridinol Photobases" in Journal of Physical Chemistry A, 121, no. 2 (2017):448-457,
https://doi.org/10.1021/acs.jpca.6b10980 . .

TY  - JOUR
AU  - Lazić, Jelena
AU  - Spasić, Jelena
AU  - Francuski, Djordje
AU  - Tokić-Vujosević, Zorana
AU  - Nikodinović-Runić, Jasmina
AU  - Maslak, Veselin
AU  - Đokić, Lidija
PY  - 2016
UR  - https://imagine.imgge.bg.ac.rs/handle/123456789/929
AB  - Michael addition of aldehydes to nitro-olefins is an effective method to obtain useful chiral gamma-nitroaldehydes. gamma-Nitroaldehydes are precursors for chiral gamma-aminobutyric acid analogues, which have numerous pharmacological activities and are used for the treatment of neurological disorders. A whole-cell system based on recombinantly expressed 4-oxalocrotonate tautomerase (4-OT) was developed and shown to be an effective biocatalyst for the Michael addition of branched aldehydes to beta-nitrostyrenes. The aim of this study was to investigate the influence of the substitution of the N-terminal proline with lysine and arginine, both containing a reactive epsilon-amino group, on the Michael addition catalyzed by 4-OT. First, the effects of these mutations were examined by in silico analysis, followed by the generation of three terminal lysine mutants. The generated mutants, 4-OT_K, 4-OT_PK and 4-OT_KK were tested for their ability to utilise beta-nitrostyrene (1), (E)-1-nitro-2-(2-thienyl)ethene (2) and trans-p-chloro-beta-nitrostyrene (3) as Michael acceptors with isobutanal (2-methylpropanal) as the donor. For comparison, the lithium salt of lysine was used in the same organocatalytic reactions. In general, the introduction of lysine had a negative effect on Michael additions based on overall product yields. However, additional lysine residues at the N-terminus of the protein resulted in structural changes that enhanced the activity towards 2 and 3. Therefore, the N-terminal proline is important for 4-OT-catalysed Michael-additions, but it is not essential.
PB  - Srpsko hemijsko društvo, Beograd
T2  - Journal of the Serbian Chemical Society
T1  - Importance of N-terminal proline for the promiscuous activity of 4-oxalocrotonate tautomerase (4-OT)
EP  - 881
IS  - 8
SP  - 871
VL  - 81
DO  - 10.2298/JSC160222053L
ER  - 

@article{
author = "Lazić, Jelena and Spasić, Jelena and Francuski, Djordje and Tokić-Vujosević, Zorana and Nikodinović-Runić, Jasmina and Maslak, Veselin and Đokić, Lidija",
year = "2016",
abstract = "Michael addition of aldehydes to nitro-olefins is an effective method to obtain useful chiral gamma-nitroaldehydes. gamma-Nitroaldehydes are precursors for chiral gamma-aminobutyric acid analogues, which have numerous pharmacological activities and are used for the treatment of neurological disorders. A whole-cell system based on recombinantly expressed 4-oxalocrotonate tautomerase (4-OT) was developed and shown to be an effective biocatalyst for the Michael addition of branched aldehydes to beta-nitrostyrenes. The aim of this study was to investigate the influence of the substitution of the N-terminal proline with lysine and arginine, both containing a reactive epsilon-amino group, on the Michael addition catalyzed by 4-OT. First, the effects of these mutations were examined by in silico analysis, followed by the generation of three terminal lysine mutants. The generated mutants, 4-OT_K, 4-OT_PK and 4-OT_KK were tested for their ability to utilise beta-nitrostyrene (1), (E)-1-nitro-2-(2-thienyl)ethene (2) and trans-p-chloro-beta-nitrostyrene (3) as Michael acceptors with isobutanal (2-methylpropanal) as the donor. For comparison, the lithium salt of lysine was used in the same organocatalytic reactions. In general, the introduction of lysine had a negative effect on Michael additions based on overall product yields. However, additional lysine residues at the N-terminus of the protein resulted in structural changes that enhanced the activity towards 2 and 3. Therefore, the N-terminal proline is important for 4-OT-catalysed Michael-additions, but it is not essential.",
publisher = "Srpsko hemijsko društvo, Beograd",
journal = "Journal of the Serbian Chemical Society",
title = "Importance of N-terminal proline for the promiscuous activity of 4-oxalocrotonate tautomerase (4-OT)",
pages = "881-871",
number = "8",
volume = "81",
doi = "10.2298/JSC160222053L"
}

Lazić, J., Spasić, J., Francuski, D., Tokić-Vujosević, Z., Nikodinović-Runić, J., Maslak, V.,& Đokić, L.. (2016). Importance of N-terminal proline for the promiscuous activity of 4-oxalocrotonate tautomerase (4-OT). in Journal of the Serbian Chemical Society
Srpsko hemijsko društvo, Beograd., 81(8), 871-881.
https://doi.org/10.2298/JSC160222053L

Lazić J, Spasić J, Francuski D, Tokić-Vujosević Z, Nikodinović-Runić J, Maslak V, Đokić L. Importance of N-terminal proline for the promiscuous activity of 4-oxalocrotonate tautomerase (4-OT). in Journal of the Serbian Chemical Society. 2016;81(8):871-881.
doi:10.2298/JSC160222053L .

Lazić, Jelena, Spasić, Jelena, Francuski, Djordje, Tokić-Vujosević, Zorana, Nikodinović-Runić, Jasmina, Maslak, Veselin, Đokić, Lidija, "Importance of N-terminal proline for the promiscuous activity of 4-oxalocrotonate tautomerase (4-OT)" in Journal of the Serbian Chemical Society, 81, no. 8 (2016):871-881,
https://doi.org/10.2298/JSC160222053L . .

TY  - JOUR
AU  - Milovanović, Jelena
AU  - Škaro Bogojević, Sanja
AU  - Šenerović, Lidija
AU  - Vasiljević, Branka
AU  - Guzik, Maciej
AU  - Kenny, Shane T.
AU  - Maslak, Veselin
AU  - Nikodinović-Runić, Jasmina
AU  - O'Connor, Kevin 
PY  - 2016
UR  - https://imagine.imgge.bg.ac.rs/handle/123456789/974
AB  - A library of 18 different compounds was synthesized starting from (R)-3-hydroxyoctanoic acid which is derived from the bacterial polymer polyhydroxyalkanoate (PHA). Ten derivatives, including halo and unsaturated methyl and benzyl esters, were synthesized and characterized for the first time. Given that (R)-3-hydroxyalkanoic acids are known to have biological activity, the new compounds were evaluated for antimicrobial activity and in vitro antiproliferative effect with mammalian cell lines. The presence of the carboxylic group was essential for the antimicrobial activity, with minimal inhibitory concentrations against a panel of bacteria (Gram-positive and Gram-negative) and fungi (Candida albicans and Microsporum gypseum) in the range 2.8-7.0 mM and 0.1-6.3 mM, respectively. 3-Halogenated octanoic acids exhibited the ability to inhibit C. albicans hyphae formation. In addition, (R)-3-hydroxyoctanoic and (E)-oct-2-enoic acids inhibited quorum sensing-regulated pyocyanin production in the opportunistic pathogen Pseudomonas aeruginosa PAO1. Generally, derivatives did not inhibit mammalian cell proliferation even at 3-mM concentrations, while only (E)-oct-2-enoic and 3-oxooctanoic acid had IC50 values of 1.7 and 1.6 mM with the human lung fibroblast cell line.
PB  - Springer, New York
T2  - Applied Microbiology and Biotechnology
T1  - Polyhydroxyalkanoate-based 3-hydroxyoctanoic acid and its derivatives as a platform of bioactive compounds
EP  - 172
IS  - 1
SP  - 161
VL  - 100
DO  - 10.1007/s00253-015-6984-4
ER  - 

@article{
author = "Milovanović, Jelena and Škaro Bogojević, Sanja and Šenerović, Lidija and Vasiljević, Branka and Guzik, Maciej and Kenny, Shane T. and Maslak, Veselin and Nikodinović-Runić, Jasmina and O'Connor, Kevin ",
year = "2016",
abstract = "A library of 18 different compounds was synthesized starting from (R)-3-hydroxyoctanoic acid which is derived from the bacterial polymer polyhydroxyalkanoate (PHA). Ten derivatives, including halo and unsaturated methyl and benzyl esters, were synthesized and characterized for the first time. Given that (R)-3-hydroxyalkanoic acids are known to have biological activity, the new compounds were evaluated for antimicrobial activity and in vitro antiproliferative effect with mammalian cell lines. The presence of the carboxylic group was essential for the antimicrobial activity, with minimal inhibitory concentrations against a panel of bacteria (Gram-positive and Gram-negative) and fungi (Candida albicans and Microsporum gypseum) in the range 2.8-7.0 mM and 0.1-6.3 mM, respectively. 3-Halogenated octanoic acids exhibited the ability to inhibit C. albicans hyphae formation. In addition, (R)-3-hydroxyoctanoic and (E)-oct-2-enoic acids inhibited quorum sensing-regulated pyocyanin production in the opportunistic pathogen Pseudomonas aeruginosa PAO1. Generally, derivatives did not inhibit mammalian cell proliferation even at 3-mM concentrations, while only (E)-oct-2-enoic and 3-oxooctanoic acid had IC50 values of 1.7 and 1.6 mM with the human lung fibroblast cell line.",
publisher = "Springer, New York",
journal = "Applied Microbiology and Biotechnology",
title = "Polyhydroxyalkanoate-based 3-hydroxyoctanoic acid and its derivatives as a platform of bioactive compounds",
pages = "172-161",
number = "1",
volume = "100",
doi = "10.1007/s00253-015-6984-4"
}

Milovanović, J., Škaro Bogojević, S., Šenerović, L., Vasiljević, B., Guzik, M., Kenny, S. T., Maslak, V., Nikodinović-Runić, J.,& O'Connor, K.. (2016). Polyhydroxyalkanoate-based 3-hydroxyoctanoic acid and its derivatives as a platform of bioactive compounds. in Applied Microbiology and Biotechnology
Springer, New York., 100(1), 161-172.
https://doi.org/10.1007/s00253-015-6984-4

Milovanović J, Škaro Bogojević S, Šenerović L, Vasiljević B, Guzik M, Kenny ST, Maslak V, Nikodinović-Runić J, O'Connor K. Polyhydroxyalkanoate-based 3-hydroxyoctanoic acid and its derivatives as a platform of bioactive compounds. in Applied Microbiology and Biotechnology. 2016;100(1):161-172.
doi:10.1007/s00253-015-6984-4 .

Milovanović, Jelena, Škaro Bogojević, Sanja, Šenerović, Lidija, Vasiljević, Branka, Guzik, Maciej, Kenny, Shane T., Maslak, Veselin, Nikodinović-Runić, Jasmina, O'Connor, Kevin , "Polyhydroxyalkanoate-based 3-hydroxyoctanoic acid and its derivatives as a platform of bioactive compounds" in Applied Microbiology and Biotechnology, 100, no. 1 (2016):161-172,
https://doi.org/10.1007/s00253-015-6984-4 . .

TY  - JOUR
AU  - Szwej, Emilia
AU  - Devocelle, Marc
AU  - Kenny, Shane
AU  - Guzik, Maciej
AU  - O'Connor, Stephen
AU  - Nikodinović-Runić, Jasmina
AU  - Milovanović, Jelena
AU  - Maslak, Veselin
AU  - Byrne, Annete T.
AU  - Gallagher, William M.
AU  - Zulian, Qun Ren
AU  - Zinn, Manfred
AU  - O'Connor, Kevin 
PY  - 2015
UR  - https://imagine.imgge.bg.ac.rs/handle/123456789/877
AB  - Conjugation of DP18L peptide with (R)-3-hydroxydecanoic acid, derived from the biopolymer polyhydroxyalkanoate, enhances its anti-cancer activity (O'Connor et al., 2013. Biomaterials 34, 2710-2718). However, it is unknown if other (R)-3-hydroxyalkanoic acids (R3HA5) can enhance peptide activity, if chain length affects enhancement, and what effect R3HA5 have on peptide structure. Here we show that the degree of enhancement of peptide (DP18L) anti-cancer activity by R3HA5 is carbon chain length dependent. In all but one example the R3HA conjugated peptides were more active against cancer cells than the unconjugated peptides. However, R3HA5 with 9 and 10 carbons were most effective at improving DPI 8L activity. DPI 8L peptide variant DPI 7L, missing a hydrophobic amino acid (leucine residue 4) exhibited lower efficacy against MiaPaCa cells. Circular dichroism analysis showed DP17L had a lower alpha helix content and the conjugation of any R3HA ((R)-3-hydroxyhexanoic acid to (R)-3-hydroxydodecanoic acid) to DPI 7L returned the helix content back to levels of DPI 8L. However (R)-3-hydroxyhexanoic did not enhance the anti-cancer activity of DPI 7L and at least 7 carbons were needed in the R3HA to enhance activity of D17L. DP17L needs a longer chain R3HA to achieve the same activity as DP18L conjugated to an R3HA. As a first step to assess the synthetic potential of polyhydroxyalkanoate derived R3HA5, (R)-3-hydroxydecanoic acid was synthetically converted to (+/-)3-chlorodecanoic acid, which when conjugated to DP18L improved its antiproliferative activity against MiaPaCa cells.
PB  - Elsevier Science Bv, Amsterdam
T2  - Journal of Biotechnology
T1  - The chain length of biologically produced (R)-3-hydroxyalkanoic acid affects biological activity and structure of anti-cancer peptides
EP  - 12
SP  - 7
VL  - 204
DO  - 10.1016/j.jbiotec.2015.02.036
ER  - 

@article{
author = "Szwej, Emilia and Devocelle, Marc and Kenny, Shane and Guzik, Maciej and O'Connor, Stephen and Nikodinović-Runić, Jasmina and Milovanović, Jelena and Maslak, Veselin and Byrne, Annete T. and Gallagher, William M. and Zulian, Qun Ren and Zinn, Manfred and O'Connor, Kevin ",
year = "2015",
abstract = "Conjugation of DP18L peptide with (R)-3-hydroxydecanoic acid, derived from the biopolymer polyhydroxyalkanoate, enhances its anti-cancer activity (O'Connor et al., 2013. Biomaterials 34, 2710-2718). However, it is unknown if other (R)-3-hydroxyalkanoic acids (R3HA5) can enhance peptide activity, if chain length affects enhancement, and what effect R3HA5 have on peptide structure. Here we show that the degree of enhancement of peptide (DP18L) anti-cancer activity by R3HA5 is carbon chain length dependent. In all but one example the R3HA conjugated peptides were more active against cancer cells than the unconjugated peptides. However, R3HA5 with 9 and 10 carbons were most effective at improving DPI 8L activity. DPI 8L peptide variant DPI 7L, missing a hydrophobic amino acid (leucine residue 4) exhibited lower efficacy against MiaPaCa cells. Circular dichroism analysis showed DP17L had a lower alpha helix content and the conjugation of any R3HA ((R)-3-hydroxyhexanoic acid to (R)-3-hydroxydodecanoic acid) to DPI 7L returned the helix content back to levels of DPI 8L. However (R)-3-hydroxyhexanoic did not enhance the anti-cancer activity of DPI 7L and at least 7 carbons were needed in the R3HA to enhance activity of D17L. DP17L needs a longer chain R3HA to achieve the same activity as DP18L conjugated to an R3HA. As a first step to assess the synthetic potential of polyhydroxyalkanoate derived R3HA5, (R)-3-hydroxydecanoic acid was synthetically converted to (+/-)3-chlorodecanoic acid, which when conjugated to DP18L improved its antiproliferative activity against MiaPaCa cells.",
publisher = "Elsevier Science Bv, Amsterdam",
journal = "Journal of Biotechnology",
title = "The chain length of biologically produced (R)-3-hydroxyalkanoic acid affects biological activity and structure of anti-cancer peptides",
pages = "12-7",
volume = "204",
doi = "10.1016/j.jbiotec.2015.02.036"
}

Szwej, E., Devocelle, M., Kenny, S., Guzik, M., O'Connor, S., Nikodinović-Runić, J., Milovanović, J., Maslak, V., Byrne, A. T., Gallagher, W. M., Zulian, Q. R., Zinn, M.,& O'Connor, K.. (2015). The chain length of biologically produced (R)-3-hydroxyalkanoic acid affects biological activity and structure of anti-cancer peptides. in Journal of Biotechnology
Elsevier Science Bv, Amsterdam., 204, 7-12.
https://doi.org/10.1016/j.jbiotec.2015.02.036

Szwej E, Devocelle M, Kenny S, Guzik M, O'Connor S, Nikodinović-Runić J, Milovanović J, Maslak V, Byrne AT, Gallagher WM, Zulian QR, Zinn M, O'Connor K. The chain length of biologically produced (R)-3-hydroxyalkanoic acid affects biological activity and structure of anti-cancer peptides. in Journal of Biotechnology. 2015;204:7-12.
doi:10.1016/j.jbiotec.2015.02.036 .

Szwej, Emilia, Devocelle, Marc, Kenny, Shane, Guzik, Maciej, O'Connor, Stephen, Nikodinović-Runić, Jasmina, Milovanović, Jelena, Maslak, Veselin, Byrne, Annete T., Gallagher, William M., Zulian, Qun Ren, Zinn, Manfred, O'Connor, Kevin , "The chain length of biologically produced (R)-3-hydroxyalkanoic acid affects biological activity and structure of anti-cancer peptides" in Journal of Biotechnology, 204 (2015):7-12,
https://doi.org/10.1016/j.jbiotec.2015.02.036 . .

TY  - JOUR
AU  - Jovanović, Predrag
AU  - Jeremić, Sanja
AU  - Đokić, Lidija
AU  - Savić, Vladimir
AU  - Milovanović, Jelena
AU  - Maslak, Veselin
AU  - Ivković, Branka
AU  - Vasiljević, Branka
AU  - Nikodinović-Runić, Jasmina
PY  - 2014
UR  - https://imagine.imgge.bg.ac.rs/handle/123456789/716
AB  - Chemoselective reduction of activated carbon-carbon double bond in conjugated nitroalkenes was achieved using Escherichia coli BL21(DE3) whole cells. Nine different substrates have been used furnishing the reduced products in moderate to good yields. 1-Nitro-4-phenyl-1,3-butadiene and (2-nitro-1-propenyl)benzene were successfully biotransformed with corresponding product yields of 54% and 45% respectively. Using this simple and environmentally friendly system 2-(2-nitropropyl)pyridine and 2-(2-nitropropyl)naphthalene were synthesized and characterized for the first time. High substrate conversion efficiency was coupled with low enantioselectivity, however 29% enantiomeric excess was detected in the case of 2-(2-nitropropyl)pyridine. It was shown that electronic properties of the aromatic ring, which affected polarity of the double bond, were not highly influential factors in the reduction process, but the presence of the nitro functionality was essential for the reaction to proceed. 1-Phenyl-4-nitro-1,3-butadiene could not be biotransformed by whole cells of Pseudomonas putida KT2440 or Bacillus subtilis 168 while it was successfully reduced by E. coli DH5 alpha but with lower efficiency in comparison to E. coli BL21(DE3). Knockout mutant affected in nemA gene coding for N-ethylmaleimide reductase (BL21 Delta nemA) could still catalyze bioreductions suggesting multiple active reductases within E. coli BL21(DE3) biocatalyst. The described biocatalytic reduction of substituted nitroalkenes provides an efficient route for the preparation of the corresponding nitroalkanes and introduces the new application of the strain traditionally utilized for recombinant protein expression.
PB  - Elsevier Science Inc, New York
T2  - Enzyme and Microbial Technology
T1  - Chemoselective biocatalytic reduction of conjugated nitroalkenes: New application for an Escherichia coli BL21(DE3) expression strain
EP  - 23
SP  - 16
VL  - 60
DO  - 10.1016/j.enzmictec.2014.03.010
ER  - 

@article{
author = "Jovanović, Predrag and Jeremić, Sanja and Đokić, Lidija and Savić, Vladimir and Milovanović, Jelena and Maslak, Veselin and Ivković, Branka and Vasiljević, Branka and Nikodinović-Runić, Jasmina",
year = "2014",
abstract = "Chemoselective reduction of activated carbon-carbon double bond in conjugated nitroalkenes was achieved using Escherichia coli BL21(DE3) whole cells. Nine different substrates have been used furnishing the reduced products in moderate to good yields. 1-Nitro-4-phenyl-1,3-butadiene and (2-nitro-1-propenyl)benzene were successfully biotransformed with corresponding product yields of 54% and 45% respectively. Using this simple and environmentally friendly system 2-(2-nitropropyl)pyridine and 2-(2-nitropropyl)naphthalene were synthesized and characterized for the first time. High substrate conversion efficiency was coupled with low enantioselectivity, however 29% enantiomeric excess was detected in the case of 2-(2-nitropropyl)pyridine. It was shown that electronic properties of the aromatic ring, which affected polarity of the double bond, were not highly influential factors in the reduction process, but the presence of the nitro functionality was essential for the reaction to proceed. 1-Phenyl-4-nitro-1,3-butadiene could not be biotransformed by whole cells of Pseudomonas putida KT2440 or Bacillus subtilis 168 while it was successfully reduced by E. coli DH5 alpha but with lower efficiency in comparison to E. coli BL21(DE3). Knockout mutant affected in nemA gene coding for N-ethylmaleimide reductase (BL21 Delta nemA) could still catalyze bioreductions suggesting multiple active reductases within E. coli BL21(DE3) biocatalyst. The described biocatalytic reduction of substituted nitroalkenes provides an efficient route for the preparation of the corresponding nitroalkanes and introduces the new application of the strain traditionally utilized for recombinant protein expression.",
publisher = "Elsevier Science Inc, New York",
journal = "Enzyme and Microbial Technology",
title = "Chemoselective biocatalytic reduction of conjugated nitroalkenes: New application for an Escherichia coli BL21(DE3) expression strain",
pages = "23-16",
volume = "60",
doi = "10.1016/j.enzmictec.2014.03.010"
}

Jovanović, P., Jeremić, S., Đokić, L., Savić, V., Milovanović, J., Maslak, V., Ivković, B., Vasiljević, B.,& Nikodinović-Runić, J.. (2014). Chemoselective biocatalytic reduction of conjugated nitroalkenes: New application for an Escherichia coli BL21(DE3) expression strain. in Enzyme and Microbial Technology
Elsevier Science Inc, New York., 60, 16-23.
https://doi.org/10.1016/j.enzmictec.2014.03.010

Jovanović P, Jeremić S, Đokić L, Savić V, Milovanović J, Maslak V, Ivković B, Vasiljević B, Nikodinović-Runić J. Chemoselective biocatalytic reduction of conjugated nitroalkenes: New application for an Escherichia coli BL21(DE3) expression strain. in Enzyme and Microbial Technology. 2014;60:16-23.
doi:10.1016/j.enzmictec.2014.03.010 .

Jovanović, Predrag, Jeremić, Sanja, Đokić, Lidija, Savić, Vladimir, Milovanović, Jelena, Maslak, Veselin, Ivković, Branka, Vasiljević, Branka, Nikodinović-Runić, Jasmina, "Chemoselective biocatalytic reduction of conjugated nitroalkenes: New application for an Escherichia coli BL21(DE3) expression strain" in Enzyme and Microbial Technology, 60 (2014):16-23,
https://doi.org/10.1016/j.enzmictec.2014.03.010 . .

TY  - JOUR
AU  - Milovanović, Jelena
AU  - Minovska, Gordana
AU  - Šenerović, Lidija
AU  - O'Connor, Kevin
AU  - Jovanović, Predrag
AU  - Savić, Vladimir
AU  - Tokić-Vujosević, Zorana
AU  - Nikodinović-Runić, Jasmina
AU  - Maslak, Veselin
PY  - 2014
UR  - https://imagine.imgge.bg.ac.rs/handle/123456789/759
AB  - Synthesis of gamma-nitroaldehydes from branched chain aldehydes and a range of alpha,beta-unsaturated nitroalkenes was achieved by a whole-cell biocatalytic reaction using 4-oxalocrotonate tautomerase as catalyst. Under mild conditions, cyclic and acyclic branched aldehydes were converted into synthetically valuable quaternary carbon containing gamma-nitroaldehydes. The yields of the desired products were influenced by reaction condition parameters such as organic solvent, temperature and pH. The whole-cell biocatalytic approach to the generation of alpha,alpha-substituted gamma-nitroaldehydes was compared to the organocatalytic approach involving the lithium salt of phenylalanine as a catalyst. As the resulting gamma-nitroaldehydes exhibited moderate antifungal activity and mild in vitro cytotoxicity against human fibroblasts (0.2-0.4 mM) they could further be examined as potentially useful pharmaceutical synthons.
PB  - Royal Soc Chemistry, Cambridge
T2  - RSC Advances
T1  - Synthesis of gamma-nitroaldehydes containing quaternary carbon in the alpha-position using a 4-oxalocrotonate tautomerase whole-cell biocatalyst
EP  - 60510
IS  - 105
SP  - 60502
VL  - 4
DO  - 10.1039/c4ra05517a
ER  - 

@article{
author = "Milovanović, Jelena and Minovska, Gordana and Šenerović, Lidija and O'Connor, Kevin and Jovanović, Predrag and Savić, Vladimir and Tokić-Vujosević, Zorana and Nikodinović-Runić, Jasmina and Maslak, Veselin",
year = "2014",
abstract = "Synthesis of gamma-nitroaldehydes from branched chain aldehydes and a range of alpha,beta-unsaturated nitroalkenes was achieved by a whole-cell biocatalytic reaction using 4-oxalocrotonate tautomerase as catalyst. Under mild conditions, cyclic and acyclic branched aldehydes were converted into synthetically valuable quaternary carbon containing gamma-nitroaldehydes. The yields of the desired products were influenced by reaction condition parameters such as organic solvent, temperature and pH. The whole-cell biocatalytic approach to the generation of alpha,alpha-substituted gamma-nitroaldehydes was compared to the organocatalytic approach involving the lithium salt of phenylalanine as a catalyst. As the resulting gamma-nitroaldehydes exhibited moderate antifungal activity and mild in vitro cytotoxicity against human fibroblasts (0.2-0.4 mM) they could further be examined as potentially useful pharmaceutical synthons.",
publisher = "Royal Soc Chemistry, Cambridge",
journal = "RSC Advances",
title = "Synthesis of gamma-nitroaldehydes containing quaternary carbon in the alpha-position using a 4-oxalocrotonate tautomerase whole-cell biocatalyst",
pages = "60510-60502",
number = "105",
volume = "4",
doi = "10.1039/c4ra05517a"
}

Milovanović, J., Minovska, G., Šenerović, L., O'Connor, K., Jovanović, P., Savić, V., Tokić-Vujosević, Z., Nikodinović-Runić, J.,& Maslak, V.. (2014). Synthesis of gamma-nitroaldehydes containing quaternary carbon in the alpha-position using a 4-oxalocrotonate tautomerase whole-cell biocatalyst. in RSC Advances
Royal Soc Chemistry, Cambridge., 4(105), 60502-60510.
https://doi.org/10.1039/c4ra05517a

Milovanović J, Minovska G, Šenerović L, O'Connor K, Jovanović P, Savić V, Tokić-Vujosević Z, Nikodinović-Runić J, Maslak V. Synthesis of gamma-nitroaldehydes containing quaternary carbon in the alpha-position using a 4-oxalocrotonate tautomerase whole-cell biocatalyst. in RSC Advances. 2014;4(105):60502-60510.
doi:10.1039/c4ra05517a .

Milovanović, Jelena, Minovska, Gordana, Šenerović, Lidija, O'Connor, Kevin, Jovanović, Predrag, Savić, Vladimir, Tokić-Vujosević, Zorana, Nikodinović-Runić, Jasmina, Maslak, Veselin, "Synthesis of gamma-nitroaldehydes containing quaternary carbon in the alpha-position using a 4-oxalocrotonate tautomerase whole-cell biocatalyst" in RSC Advances, 4, no. 105 (2014):60502-60510,
https://doi.org/10.1039/c4ra05517a . .

TY  - JOUR
AU  - Narancić, Tanja
AU  - Milovanović, Jelena
AU  - Jovanović, Predrag
AU  - Francuski, Djordje
AU  - Bigović, Miljan
AU  - Maslak, Veselin
AU  - Savić, Vladimir
AU  - Vasiljević, Branka
AU  - O'Connor, Kevin 
AU  - Nikodinović-Runić, Jasmina
PY  - 2013
UR  - https://imagine.imgge.bg.ac.rs/handle/123456789/656
AB  - A novel whole cell system based on recombinantly expressed 4-oxalocrotonate tautomerase (4-OT) was developed and shown to be an effective biocatalyst for the asymmetric Michael addition of acetaldehyde to beta-nitrostyrenes. Optimal ratio of substrates (2 mM beta-nitrostyrenes and 20 mM acetaldehyde) and biocatalyst of 5 g of cell dry weight of biocatalyst per liter was determined. Through further bioprocess improvement by sequential addition of substrate 10 mM nitrostyrene biotransformation was achieved within 150 min. Excellent enantioselectivity ( gt 99% ee) and product yields of up to 60% were obtained with beta-nitrostyrene substrate. The biotransformation product, 4-nitro-3-phenyl-butanal, was isolated from aqueous media and further transformed into the corresponding amino alcohol. The biocatalyst exhibited lower reaction rates with p-Cl-, o-Cl- and p-F-beta-nitrostyrenes with product yields of 38%, 51%, 31% and ee values of 84%, 88% and 94% respectively. The importance of the terminal,proline of 4-UT was confirmed by two proline enriched variants and homology modeling.
PB  - Elsevier Sci Ltd, Oxford
T2  - Bioresource Technology
T1  - Highly efficient Michael-type addition of acetaldehyde to beta-nitrostyrenes by whole resting cells of Escherichia coli expressing 4-oxalocrotonate tautomerase
EP  - 468
SP  - 462
VL  - 142
DO  - 10.1016/j.biortech.2013.05.074
ER  - 

@article{
author = "Narancić, Tanja and Milovanović, Jelena and Jovanović, Predrag and Francuski, Djordje and Bigović, Miljan and Maslak, Veselin and Savić, Vladimir and Vasiljević, Branka and O'Connor, Kevin  and Nikodinović-Runić, Jasmina",
year = "2013",
abstract = "A novel whole cell system based on recombinantly expressed 4-oxalocrotonate tautomerase (4-OT) was developed and shown to be an effective biocatalyst for the asymmetric Michael addition of acetaldehyde to beta-nitrostyrenes. Optimal ratio of substrates (2 mM beta-nitrostyrenes and 20 mM acetaldehyde) and biocatalyst of 5 g of cell dry weight of biocatalyst per liter was determined. Through further bioprocess improvement by sequential addition of substrate 10 mM nitrostyrene biotransformation was achieved within 150 min. Excellent enantioselectivity ( gt 99% ee) and product yields of up to 60% were obtained with beta-nitrostyrene substrate. The biotransformation product, 4-nitro-3-phenyl-butanal, was isolated from aqueous media and further transformed into the corresponding amino alcohol. The biocatalyst exhibited lower reaction rates with p-Cl-, o-Cl- and p-F-beta-nitrostyrenes with product yields of 38%, 51%, 31% and ee values of 84%, 88% and 94% respectively. The importance of the terminal,proline of 4-UT was confirmed by two proline enriched variants and homology modeling.",
publisher = "Elsevier Sci Ltd, Oxford",
journal = "Bioresource Technology",
title = "Highly efficient Michael-type addition of acetaldehyde to beta-nitrostyrenes by whole resting cells of Escherichia coli expressing 4-oxalocrotonate tautomerase",
pages = "468-462",
volume = "142",
doi = "10.1016/j.biortech.2013.05.074"
}

Narancić, T., Milovanović, J., Jovanović, P., Francuski, D., Bigović, M., Maslak, V., Savić, V., Vasiljević, B., O'Connor, K.,& Nikodinović-Runić, J.. (2013). Highly efficient Michael-type addition of acetaldehyde to beta-nitrostyrenes by whole resting cells of Escherichia coli expressing 4-oxalocrotonate tautomerase. in Bioresource Technology
Elsevier Sci Ltd, Oxford., 142, 462-468.
https://doi.org/10.1016/j.biortech.2013.05.074

Narancić T, Milovanović J, Jovanović P, Francuski D, Bigović M, Maslak V, Savić V, Vasiljević B, O'Connor K, Nikodinović-Runić J. Highly efficient Michael-type addition of acetaldehyde to beta-nitrostyrenes by whole resting cells of Escherichia coli expressing 4-oxalocrotonate tautomerase. in Bioresource Technology. 2013;142:462-468.
doi:10.1016/j.biortech.2013.05.074 .

Narancić, Tanja, Milovanović, Jelena, Jovanović, Predrag, Francuski, Djordje, Bigović, Miljan, Maslak, Veselin, Savić, Vladimir, Vasiljević, Branka, O'Connor, Kevin , Nikodinović-Runić, Jasmina, "Highly efficient Michael-type addition of acetaldehyde to beta-nitrostyrenes by whole resting cells of Escherichia coli expressing 4-oxalocrotonate tautomerase" in Bioresource Technology, 142 (2013):462-468,
https://doi.org/10.1016/j.biortech.2013.05.074 . .

TY  - JOUR
AU  - Bigović, Miljan
AU  - Škaro Bogojević, Sanja
AU  - Maslak, Veselin
AU  - Saicić, Radomir N.
PY  - 2013
UR  - https://imagine.imgge.bg.ac.rs/handle/123456789/668
AB  - Cyclic enol carbonates of type 2, obtained via the indium-promoted allylation of aldehydes with 4-(bromomethyl)-1,3-dioxol-2-one, undergo Heck reaction with aryl iodides in the presence of silver trifluoroacetate, to give the corresponding arylated products. Thus, 4-(bromomethyl)-1,3-dioxol-2-one can be considered as a synthetic equivalent of 3-mylhydroxyacetone enolate.
PB  - Pergamon-Elsevier Science Ltd, Oxford
T2  - Tetrahedron Letters
T1  - Expanding the scope of the indium-promoted allylation reaction: 4-(bromomethyl)-1,3-dioxol-2-one as a synthetic equivalent of a 3-arylhydroxyacetone enolate
EP  - 6626
IS  - 48
SP  - 6624
VL  - 54
DO  - 10.1016/j.tetlet.2013.09.115
ER  - 

@article{
author = "Bigović, Miljan and Škaro Bogojević, Sanja and Maslak, Veselin and Saicić, Radomir N.",
year = "2013",
abstract = "Cyclic enol carbonates of type 2, obtained via the indium-promoted allylation of aldehydes with 4-(bromomethyl)-1,3-dioxol-2-one, undergo Heck reaction with aryl iodides in the presence of silver trifluoroacetate, to give the corresponding arylated products. Thus, 4-(bromomethyl)-1,3-dioxol-2-one can be considered as a synthetic equivalent of 3-mylhydroxyacetone enolate.",
publisher = "Pergamon-Elsevier Science Ltd, Oxford",
journal = "Tetrahedron Letters",
title = "Expanding the scope of the indium-promoted allylation reaction: 4-(bromomethyl)-1,3-dioxol-2-one as a synthetic equivalent of a 3-arylhydroxyacetone enolate",
pages = "6626-6624",
number = "48",
volume = "54",
doi = "10.1016/j.tetlet.2013.09.115"
}

Bigović, M., Škaro Bogojević, S., Maslak, V.,& Saicić, R. N.. (2013). Expanding the scope of the indium-promoted allylation reaction: 4-(bromomethyl)-1,3-dioxol-2-one as a synthetic equivalent of a 3-arylhydroxyacetone enolate. in Tetrahedron Letters
Pergamon-Elsevier Science Ltd, Oxford., 54(48), 6624-6626.
https://doi.org/10.1016/j.tetlet.2013.09.115

Bigović M, Škaro Bogojević S, Maslak V, Saicić RN. Expanding the scope of the indium-promoted allylation reaction: 4-(bromomethyl)-1,3-dioxol-2-one as a synthetic equivalent of a 3-arylhydroxyacetone enolate. in Tetrahedron Letters. 2013;54(48):6624-6626.
doi:10.1016/j.tetlet.2013.09.115 .

Bigović, Miljan, Škaro Bogojević, Sanja, Maslak, Veselin, Saicić, Radomir N., "Expanding the scope of the indium-promoted allylation reaction: 4-(bromomethyl)-1,3-dioxol-2-one as a synthetic equivalent of a 3-arylhydroxyacetone enolate" in Tetrahedron Letters, 54, no. 48 (2013):6624-6626,
https://doi.org/10.1016/j.tetlet.2013.09.115 . .