Chemoselective biocatalytic reduction of conjugated nitroalkenes: New application for an Escherichia coli BL21(DE3) expression strain
Само за регистроване кориснике
2014
Аутори
Jovanović, PredragJeremić, Sanja
Đokić, Lidija
Savić, Vladimir
Milovanović, Jelena
Maslak, Veselin
Ivković, Branka
Vasiljević, Branka
Nikodinović-Runić, Jasmina
Чланак у часопису (Објављена верзија)
Метаподаци
Приказ свих података о документуАпстракт
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.
Кључне речи:
Nitrostyrene / Nitroalkene reduction / Escherichia coli BL21(DE3) / C=C reduction / BiotransformationИзвор:
Enzyme and Microbial Technology, 2014, 60, 16-23Издавач:
- Elsevier Science Inc, New York
Финансирање / пројекти:
- Изучавање микробиолошког диверзитета и карактеризација корисних срединских микроорганизама (RS-MESTD-Basic Research (BR or ON)-173048)
- Компјутерско дизајнирање, синтеза и биолошка евалуација нових хетероцикличних једињења као селективних инхибитора туморогенезе (RS-MESTD-Basic Research (BR or ON)-172009)
DOI: 10.1016/j.enzmictec.2014.03.010
ISSN: 0141-0229
PubMed: 24835095
WoS: 000337014300003
Scopus: 2-s2.0-84903370994
Институција/група
Institut za molekularnu genetiku i genetičko inženjerstvoTY - 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 . .