Highly efficient Michael-type addition of acetaldehyde to beta-nitrostyrenes by whole resting cells of Escherichia coli expressing 4-oxalocrotonate tautomerase
Само за регистроване кориснике
2013
Аутори
Narancić, TanjaMilovanović, Jelena
Jovanović, Predrag
Francuski, Djordje
Bigović, Miljan
Maslak, Veselin
Savić, Vladimir
Vasiljević, Branka
O'Connor, Kevin
Nikodinović-Runić, Jasmina
Чланак у часопису (Објављена верзија)
Метаподаци
Приказ свих података о документуАпстракт
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 te...rminal,proline of 4-UT was confirmed by two proline enriched variants and homology modeling.
Кључне речи:
Whole cell / Nitrostyrene / Michael addition / Biocatalyst / 4-Oxalocrotonate tautomeraseИзвор:
Bioresource Technology, 2013, 142, 462-468Издавач:
- Elsevier Sci Ltd, Oxford
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)
- Комплексне болести као модел систем за проучавање модулације фенотипа-структурна и функционална анализа молекуларних биомаркера (RS-MESTD-Basic Research (BR or ON)-173008)
- Рационални дизајн и синтеза биолошки активних и координационих једињења и функционалних материјала, релевантних у (био)нанотехнологији (RS-MESTD-Basic Research (BR or ON)-172035)
DOI: 10.1016/j.biortech.2013.05.074
ISSN: 0960-8524
WoS: 000322292800061
Scopus: 2-s2.0-84879283087
Институција/група
Institut za molekularnu genetiku i genetičko inženjerstvoTY - 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 . .