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Highly efficient Michael-type addition of acetaldehyde to beta-nitrostyrenes by whole resting cells of Escherichia coli expressing 4-oxalocrotonate tautomerase
dc.creator | Narancić, Tanja | |
dc.creator | Kadivojević, Jelena | |
dc.creator | Jovanović, Predrag | |
dc.creator | Francuski, Đorđe | |
dc.creator | Bigović, Miljan | |
dc.creator | Maslak, Veselin | |
dc.creator | Savić, Vladimir | |
dc.creator | Vasiljević, Branka | |
dc.creator | O'Connor, Kevin | |
dc.creator | Nikodinović-Runić, Jasmina | |
dc.date.accessioned | 2019-09-02T11:35:22Z | |
dc.date.available | 2019-09-02T11:35:22Z | |
dc.date.issued | 2013 | |
dc.identifier.issn | 0960-8524 | |
dc.identifier.uri | https://farfar.pharmacy.bg.ac.rs/handle/123456789/1960 | |
dc.description.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. | en |
dc.publisher | Elsevier Sci Ltd, Oxford | |
dc.relation | info:eu-repo/grantAgreement/MESTD/Basic Research (BR or ON)/173048/RS// | |
dc.rights | restrictedAccess | |
dc.source | Bioresource Technology | |
dc.subject | Biocatalyst | en |
dc.subject | Michael addition | en |
dc.subject | Nitrostyrene | en |
dc.subject | 4-Oxalocrotonate tautomerase | en |
dc.subject | Whole cell | en |
dc.title | Highly efficient Michael-type addition of acetaldehyde to beta-nitrostyrenes by whole resting cells of Escherichia coli expressing 4-oxalocrotonate tautomerase | en |
dc.type | article | |
dc.rights.license | ARR | |
dcterms.abstract | Наранцић, Тања; Јовановић, Предраг; О'Цоннор, Кевин; Маслак, Веселин; Француски, Ђорђе; Биговић, Миљан; Никодиновић-Рунић, Јасмина; Кадивојевић, Јелена; Савић, Владимир; Васиљевић, Бранка; | |
dc.citation.volume | 142 | |
dc.citation.spage | 462 | |
dc.citation.epage | 468 | |
dc.citation.other | 142: 462-468 | |
dc.citation.rank | aM21 | |
dc.identifier.wos | 000322292800061 | |
dc.identifier.doi | 10.1016/j.biortech.2013.05.074 | |
dc.identifier.pmid | 23759430 | |
dc.identifier.scopus | 2-s2.0-84879283087 | |
dc.type.version | publishedVersion |