Highly efficient Michael-type addition of acetaldehyde to beta-nitrostyrenes by whole resting cells of Escherichia coli expressing 4-oxalocrotonate tautomerase
rcub.bitstream.locked
2013
Authors
Narancić, TanjaKadivojević, Jelena
Jovanović, Predrag

Francuski, Đorđe
Bigović, Miljan
Maslak, Veselin

Savić, Vladimir

Vasiljević, Branka

O'Connor, Kevin
Nikodinović-Runić, Jasmina

Article (Published version)

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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 (>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 termi...nal,proline of 4-UT was confirmed by two proline enriched variants and homology modeling.
Keywords:
Biocatalyst / Michael addition / Nitrostyrene / 4-Oxalocrotonate tautomerase / Whole cellSource:
Bioresource Technology, 2013, 142, 462-468Publisher:
- Elsevier Sci Ltd, Oxford
Funding / projects:
- Microbial diversity study and characterization of beneficial environmental microorganisms (RS-173048)
DOI: 10.1016/j.biortech.2013.05.074
ISSN: 0960-8524
PubMed: 23759430
WoS: 000322292800061
Scopus: 2-s2.0-84879283087
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Institution/Community
PharmacyTY - JOUR AU - Narancić, Tanja AU - Kadivojević, Jelena AU - Jovanović, Predrag AU - Francuski, Đorđe AU - Bigović, Miljan AU - Maslak, Veselin AU - Savić, Vladimir AU - Vasiljević, Branka AU - O'Connor, Kevin AU - Nikodinović-Runić, Jasmina PY - 2013 UR - https://farfar.pharmacy.bg.ac.rs/handle/123456789/1960 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 (>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 VL - 142 SP - 462 EP - 468 DO - 10.1016/j.biortech.2013.05.074 ER -
@article{ author = "Narancić, Tanja and Kadivojević, Jelena and Jovanović, Predrag and Francuski, Đorđe 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 (>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", volume = "142", pages = "462-468", doi = "10.1016/j.biortech.2013.05.074" }
Narancić, T., Kadivojević, J., Jovanović, P., Francuski, Đ., 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, Kadivojević J, Jovanović P, Francuski Đ, 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, Kadivojević, Jelena, Jovanović, Predrag, Francuski, Đorđe, 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 . .