Gram-scale synthesis of (S)-1-(thiophen-2-yl)ethanol in high enantiomeric purity under Enterococcus faecium BY48 biocatalysts

Basit Öğe Kaydı
dc.contributor.authorSahin, Engin
dc.date.accessioned2024-10-04T18:51:02Z
dc.date.available2024-10-04T18:51:02Z
dc.date.issued2022
dc.departmentBayburt Üniversitesien_US
dc.description.abstractSulfur-containing chiral heterocyclic secondary alcohols are relevant intermediates in the preparation of enantiomerically pure compounds endowed with biological activity. In this report, we evaluated the reductive potential of different lactic acid bacteria as whole-cell biocatalysts of the enantioselective reduction of 1-(thiophen-2-yl)ethanone (1). Enterococcus faecium BY48, isolated from boza, a cereal-based fermented beverage, was found to be the best biocatalyst in our initial investigations. Using whole-cell preparations of E. faecium BY48, we then systematically analyzed the reaction parameters (pH, incubation period, agitation speed, and temperature) to optimize the yield, the enantiomeric excess (e. e.), and the conversion leading to (S)-1-(thiophen-2-yl)ethanol [(S)-2]. The target derivative, which is a precursor in the synthesis of biologically active chiral compounds, was obtained in enantiomerically pure form, gram-scale amounts, and high yield. This is also the first report that the manufacture of (S)-2 in excellent conversion, yield, enantiopure form, and gram scale used whole-cell biocatalyst. This whole-cell E. faecium BY48 biocatalyzed reaction is a clean, environmentally friendly, and cost-effective process, representing a valuable alternative to chemical catalysis or previously reported biocatalytic procedures in the preparation of (S)-2.en_US
dc.identifier.doi10.1002/chir.23456
dc.identifier.endpage1127en_US
dc.identifier.issn0899-0042
dc.identifier.issn1520-636X
dc.identifier.issue8en_US
dc.identifier.pmid35535726en_US
dc.identifier.scopus2-s2.0-85129695898en_US
dc.identifier.scopusqualityQ3en_US
dc.identifier.startpage1120en_US
dc.identifier.urihttps://doi.org/10.1002/chir.23456
dc.identifier.urihttp://hdl.handle.net/20.500.12403/3353
dc.identifier.volume34en_US
dc.identifier.wosWOS:000792658100001en_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.subject(S)-1-(thiophen-2-yl)ethanolen_US
dc.subjectchiral hetero cyclic alcoholsen_US
dc.subjectchiralityen_US
dc.subjectEnterococcus faecium BY48en_US
dc.subjectwhole cell biocatalysten_US
dc.titleGram-scale synthesis of (S)-1-(thiophen-2-yl)ethanol in high enantiomeric purity under Enterococcus faecium BY48 biocatalystsen_US
dc.typeArticleen_US

Dosyalar

Koleksiyon

WoS İndeksli Yayınlar Koleksiyonu
PubMed İndeksli Yayın Koleksiyonu
Scopus İndeksli Yayınlar Koleksiyonu