Green synthesis of (S)-1-(furan-2-yl)propan-1-ol from asymmetric bioreduction of 1-(furan-2-yl)propan-1-one using whole-cell of Lactobacillus paracasei BD101

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dc.contributor.authorBulbul, Ali Savas
dc.contributor.authorSahin, Engin
dc.date.accessioned2024-10-04T18:51:03Z
dc.date.available2024-10-04T18:51:03Z
dc.date.issued2024
dc.departmentBayburt Üniversitesien_US
dc.description.abstractChiral heterocyclic alcohols are important precursors for production of pharmaceutical medicines and natural products. (S)-1-(furan-2-yl)propan-1-ol ((S)-2) can be used production of pyranone, which can be used in the synthesis of sugar analogues, antibiotics, tirantamycines, and anticancer drugs. The synthetic approaches for (S)-2, however, have substantial difficulties in terms of inadequate enantiomeric excess (ee) and gram scale synthesis. Moreover, the biocatalytic synthesis of (S)-2 is unknown until now. In this study, the synthesis of (S)-2 was carried out by performing the asymmetric bioreduction of 1-(furan-2-yl)propan-1-one (1) using the Lactobacillus paracasei BD101 biocatalyst obtained from boza, a grain-based fermented beverage. (S)-2 was obtained with >99% conversion, >99% ee, and 96% yield under the optimized conditions. Furthermore, in 50 h, 8.37 g of 1 was entirely transformed into (S)-2 on gram scale (96% isolated yield, 8.11 g). This is the first report on the high-gram scale biocatalyzed synthesis of enantiopure (S)-2. These data suggest that L. paracasei BD101 can be used to bioreduction of 1 in gram scale and efficiently produce (S)-2. Furthermore, these findings laid the base for future study into the biocatalytic production of (S)-2. It was particularly notable as it was the highest known to date optical purity of (S)-2 generated by asymmetric reduction using a biocatalyst. This work offers a productive environmentally friendly method for producing (S)-2 using biocatalysts.en_US
dc.description.sponsorshipThe authors thanks to Prof Enes Dertli (Yildiz Technical University) for providing the biocatalyst.en_US
dc.description.sponsorshipThe authors thanks to Prof Enes Dertli (Yildiz Technical University) for providing the biocatalyst.en_US
dc.identifier.doi10.1002/chir.23620
dc.identifier.issn0899-0042
dc.identifier.issn1520-636X
dc.identifier.issue1en_US
dc.identifier.pmid37727057en_US
dc.identifier.scopus2-s2.0-85171472870en_US
dc.identifier.scopusqualityQ3en_US
dc.identifier.urihttps://doi.org/10.1002/chir.23620
dc.identifier.urihttp://hdl.handle.net/20.500.12403/3357
dc.identifier.volume36en_US
dc.identifier.wosWOS:001068306900001en_US
dc.identifier.wosqualityQ1en_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-(furan-2-yl)propan-1-olen_US
dc.subjectasymmetric bioreductionen_US
dc.subjectdrug precursoren_US
dc.subjectgreen chemistryen_US
dc.subjectwhole-cell biocatalysten_US
dc.titleGreen synthesis of (S)-1-(furan-2-yl)propan-1-ol from asymmetric bioreduction of 1-(furan-2-yl)propan-1-one using whole-cell of Lactobacillus paracasei BD101en_US
dc.typeArticleen_US

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