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dc.creatorNarancić, Tanja
dc.creatorKadivojević, Jelena
dc.creatorJovanović, Predrag
dc.creatorFrancuski, Đorđe
dc.creatorBigović, Miljan
dc.creatorMaslak, Veselin
dc.creatorSavić, Vladimir
dc.creatorVasiljević, Branka
dc.creatorO'Connor, Kevin
dc.creatorNikodinović-Runić, Jasmina
dc.date.accessioned2019-09-02T11:35:22Z
dc.date.available2019-09-02T11:35:22Z
dc.date.issued2013
dc.identifier.issn0960-8524
dc.identifier.urihttp://farfar.pharmacy.bg.ac.rs/handle/123456789/1960
dc.description.abstractA 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.publisherElsevier Sci Ltd, Oxford
dc.relationinfo:eu-repo/grantAgreement/MESTD/Basic Research (BR or ON)/173048/RS//
dc.rightsrestrictedAccess
dc.sourceBioresource Technology
dc.subjectBiocatalysten
dc.subjectMichael additionen
dc.subjectNitrostyreneen
dc.subject4-Oxalocrotonate tautomeraseen
dc.subjectWhole cellen
dc.titleHighly efficient Michael-type addition of acetaldehyde to beta-nitrostyrenes by whole resting cells of Escherichia coli expressing 4-oxalocrotonate tautomeraseen
dc.typearticle
dc.rights.licenseARR
dcterms.abstractНаранцић, Тања; Јовановић, Предраг; О'Цоннор, Кевин; Маслак, Веселин; Француски, Ђорђе; Биговић, Миљан; Никодиновић-Рунић, Јасмина; Кадивојевић, Јелена; Савић, Владимир; Васиљевић, Бранка;
dc.citation.volume142
dc.citation.spage462
dc.citation.epage468
dc.citation.other142: 462-468
dc.citation.rankaM21
dc.identifier.wos000322292800061
dc.identifier.doi10.1016/j.biortech.2013.05.074
dc.identifier.pmid23759430
dc.identifier.scopus2-s2.0-84879283087
dc.identifier.rcubconv_2883
dc.type.versionpublishedVersion


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