Regioselective asymmetric bioreduction of trans-4-phenylbut-3-en-2-one by whole-cell of Weissella cibaria N9 biocatalyst

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dc.authoridKalay, Erbay/0000-0002-4656-8254
dc.contributor.authorKalay, Erbay
dc.contributor.authorSahin, Engin
dc.date.accessioned2024-10-04T18:52:47Z
dc.date.available2024-10-04T18:52:47Z
dc.date.issued2021
dc.departmentBayburt Üniversitesien_US
dc.description.abstractThere is a considerable interest in the asymmetric production of chiral allylic alcohols, the main building blocks of many functional molecules. The asymmetric reduction of alpha,beta-unsaturated ketones is difficult with traditional chemical protocols in a regioselective and stereoselective manner. In this study, the reductive capacity of whole cell of Leuconostoc mesenteroides N6, Weissella paramesenteroides N7, Weissella cibaria N9, and Leuconostoc pseudomesenteroides N13 was investigated as whole-cell biocatalysts in the enantioselective reduction of (E)-4-phenylbut-3-en-2-one (1). The biocatalytic reduction of 1 to (S,E)-4-phenylbut-3-en-2-ol ((S,E)-2) using the whole cell of W. cibaria N9 isolated from Turkish sourdough was developed in a regioselective fashion, occurring with excellent conversion and recovering the product in good yield. In biocatalytic reduction reactions, the conversion of the substrate and the enantiomeric excess (ee) of the product are significantly affected by optimization parameters such as temperature, agitation rate, pH, and incubation time. Effects of these parameters on ee and conversion were investigated comprehensively. In addition, to our knowledge, this is the first report on production of (S,E)-2 using whole-cell biocatalyst in excellent yield, conversion with enantiopure form and at gram scale. These findings pave the way for the use of whole cell of W. cibaria N9 for challenging higher substrate concentrations of different alpha,beta-unsaturated ketones for regioselective reduction at industrial scale.en_US
dc.identifier.doi10.1002/chir.23337
dc.identifier.endpage542en_US
dc.identifier.issn0899-0042
dc.identifier.issn1520-636X
dc.identifier.issue9en_US
dc.identifier.pmid34240754en_US
dc.identifier.scopus2-s2.0-85109370235en_US
dc.identifier.scopusqualityQ3en_US
dc.identifier.startpage535en_US
dc.identifier.urihttps://doi.org/10.1002/chir.23337
dc.identifier.urihttp://hdl.handle.net/20.500.12403/3647
dc.identifier.volume33en_US
dc.identifier.wosWOS:000670798600001en_US
dc.identifier.wosqualityQ3en_US
dc.indekslendigikaynakWeb of Scienceen_US
dc.indekslendigikaynakScopusen_US
dc.indekslendigikaynakPubMeden_US
dc.language.isoenen_US
dc.publisherWileyen_US
dc.relation.ispartofChiralityen_US
dc.relation.publicationcategoryMakale - Uluslararası Hakemli Dergi - Kurum Öğretim Elemanıen_US
dc.rightsinfo:eu-repo/semantics/closedAccessen_US
dc.subjectasymmetric reductionen_US
dc.subjectbiocatalysten_US
dc.subjectchiral allylic alcoholen_US
dc.subjectregioselective reductionen_US
dc.subject(Sen_US
dc.subjectE)-4-phenylbut-3-en-2-olen_US
dc.titleRegioselective asymmetric bioreduction of trans-4-phenylbut-3-en-2-one by whole-cell of Weissella cibaria N9 biocatalysten_US
dc.typeArticleen_US

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