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
Narančić, TanjaKadivojević, Jelena
Jovanović, Predrag M.
Francuski, Đorđe
Bigović, Miljan
Maslak, Veselin
Savić, Vladimir
Vasiljević, Branka
O'Connor, Kevin E.
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:
Biocatalyst / Michael addition / Nitrostyrene / 4-Oxalocrotonate tautomerase / Whole cellИзвор:
Bioresource Technology, 2013, 142, 462-468Издавач:
- Elsevier Sci Ltd, Oxford
Финансирање / пројекти:
- Изучавање микробиолошког диверзитета и карактеризација корисних срединских микроорганизама (RS-173048)
- Компјутерско дизајнирање, синтеза и биолошка евалуација нових хетероцикличних једињења као селективних инхибитора туморогенезе (RS-172009)
- Комплексне болести као модел систем за проучавање модулације фенотипа-структурна и функционална анализа молекуларних биомаркера (RS-173008)
- Рационални дизајн и синтеза биолошки активних и координационих једињења и функционалних материјала, релевантних у (био)нанотехнологији (RS-172035)
Напомена:
- Supplementary material: http://cherry.chem.bg.ac.rs/handle/123456789/3499
DOI: 10.1016/j.biortech.2013.05.074
ISSN: 0960-8524
PubMed: 23759430
WoS: 000322292800061
Scopus: 2-s2.0-84879283087
Институција/група
Hemijski fakultet / Faculty of ChemistryTY - JOUR AU - Narančić, Tanja AU - Kadivojević, Jelena AU - Jovanović, Predrag M. AU - Francuski, Đorđe AU - Bigović, Miljan AU - Maslak, Veselin AU - Savić, Vladimir AU - Vasiljević, Branka AU - O'Connor, Kevin E. AU - Nikodinović-Runić, Jasmina PY - 2013 UR - https://cherry.chem.bg.ac.rs/handle/123456789/1377 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 VL - 142 SP - 462 EP - 468 DO - 10.1016/j.biortech.2013.05.074 ER -
@article{ author = "Narančić, Tanja and Kadivojević, Jelena and Jovanović, Predrag M. and Francuski, Đorđe and Bigović, Miljan and Maslak, Veselin and Savić, Vladimir and Vasiljević, Branka and O'Connor, Kevin E. 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", volume = "142", pages = "462-468", doi = "10.1016/j.biortech.2013.05.074" }
Narančić, T., Kadivojević, J., Jovanović, P. M., Francuski, Đ., Bigović, M., Maslak, V., Savić, V., Vasiljević, B., O'Connor, K. E.,& 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
Narančić T, Kadivojević J, Jovanović PM, Francuski Đ, Bigović M, Maslak V, Savić V, Vasiljević B, O'Connor KE, 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 .
Narančić, Tanja, Kadivojević, Jelena, Jovanović, Predrag M., Francuski, Đorđe, Bigović, Miljan, Maslak, Veselin, Savić, Vladimir, Vasiljević, Branka, O'Connor, Kevin E., 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 . .