Efficient bioreduction of 1-(furan-2-yl)ethanone into enantiomerically pure drug precursor by Lactobacillus paracasei BD101

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dc.contributor.authorSahin, Engin
dc.date.accessioned2024-10-04T18:49:41Z
dc.date.available2024-10-04T18:49:41Z
dc.date.issued2023
dc.departmentBayburt Üniversitesien_US
dc.description.abstractAsymmetric bioreduction catalyzed by biocatalyst have shown considerable potential in the preparation of chiral alcohols. (R)-1-(furan-2-yl)ethanol ((R)-2) can be used precursor in the synthesis of many naturally bioactive piperidine alkaloids such as (-)-Cassine, (-)-Spectaline, (-)-Carnavaline, Prosafrine and (-)-Prosafrinine. Moreover, (R)-2 a key chiral precursor in the production of alpha, beta-unsaturated delta-lactones, which have antifungal, antibiotic, and cytotoxic effects on human tumor cells. However, the synthesis routes of (R)-2 still pose signif-icant challenges in term of unsatisfactory enantiomeric excess (ee) and gram scale synthesis. In this study, Lactobacillus paracasei BD101 biocatalyst from boza, a cereal-based fermented beverage, for the asymmetric bioreduction of the 1-(furan-2-yl)ethanone (1). Following biocatalytic process optimization, (R)-2 was generated with >99% ee and 97% yield. In addition, 9.9 g of 1 was completely converted into (R)-2 on a gram scale (9.78 g, 97% isolated yield) in 48 h. This is the first report about the fabrication of enantiopure (R)-2 in high gram scale using biocatalyst. The optical purity of (R)-2 produced by asymmetric reduction with L paracasei BD101 was also noteworthy since it was the highest documented to date. This study provides an efficient green process for the biocatalytic synthesis of (R)-2.en_US
dc.identifier.doi10.1016/j.mcat.2023.113037
dc.identifier.issn2468-8231
dc.identifier.scopus2-s2.0-85149213014en_US
dc.identifier.scopusqualityQ2en_US
dc.identifier.urihttps://doi.org/10.1016/j.mcat.2023.113037
dc.identifier.urihttp://hdl.handle.net/20.500.12403/3255
dc.identifier.volume539en_US
dc.identifier.wosWOS:000949059000001en_US
dc.identifier.wosqualityQ2en_US
dc.indekslendigikaynakWeb of Scienceen_US
dc.indekslendigikaynakScopusen_US
dc.language.isoenen_US
dc.publisherElsevieren_US
dc.relation.ispartofMolecular Catalysisen_US
dc.relation.publicationcategoryMakale - Uluslararası Hakemli Dergi - Kurum Öğretim Elemanıen_US
dc.rightsinfo:eu-repo/semantics/closedAccessen_US
dc.subjectDrug precursoren_US
dc.subjectWhole-cell biocatalysten_US
dc.subjectAsymmetric bioreductionen_US
dc.subjectChiral secondary alcoholen_US
dc.subject(R)-1-(furan-2-yl)ethanolen_US
dc.titleEfficient bioreduction of 1-(furan-2-yl)ethanone into enantiomerically pure drug precursor by Lactobacillus paracasei BD101en_US
dc.typeArticleen_US

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