Synthesis of gamma-nitroaldehydes containing quaternary carbon in the alpha-position using a 4-oxalocrotonate tautomerase whole-cell biocatalyst
2014
Authors
Milovanović, JelenaMinovska, Gordana
Šenerović, Lidija
O'Connor, Kevin
Jovanović, Predrag
Savić, Vladimir
Tokić-Vujosević, Zorana
Nikodinović-Runić, Jasmina
Maslak, Veselin
Article (Published version)
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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.
Source:
RSC Advances, 2014, 4, 105, 60502-60510Publisher:
- Royal Soc Chemistry, Cambridge
Funding / projects:
- Microbial diversity study and characterization of beneficial environmental microorganisms (RS-MESTD-Basic Research (BR or ON)-173048)
- Design, synthesis and investigations of fullerene based nanomolecular machines (RS-MESTD-Basic Research (BR or ON)-172002)
DOI: 10.1039/c4ra05517a
ISSN: 2046-2069
WoS: 000345655600010
Scopus: 2-s2.0-84937196259
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Institut za molekularnu genetiku i genetičko inženjerstvoTY - 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 . .