Debaryomyces hansenii as a new biocatalyst in the asymmetric reduction of substituted acetophenones

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dc.authorid37098938400
dc.contributor.authorŞahin E.
dc.date.accessioned20.04.201910:49:12
dc.date.accessioned2019-04-20T21:43:15Z
dc.date.available20.04.201910:49:12
dc.date.available2019-04-20T21:43:15Z
dc.date.issued2017
dc.departmentBayburt Üniversitesien_US
dc.description.abstractChiral secondary alcohols are convenient mediator for the synthesis of biologically active compounds and natural products. In this study fifteen yeast strains belonging to three food originated yeast species Debaryomyces hansenii, Saccharomyces cerevisiae and Hanseniaspora guilliermondii were tested for their capability for the asymmetric reduction of acetophenone to 1-phenylethanol as biocatalyst microorganisms. Of these strains, Debaryomyces hansenii P1 strain showed an effective asymmetric reduction ability. Under optimized conditions, substituted acetophenones were converted to the corresponding optically active secondary alcohols in up to 99% enantiomeric excess and at high conversion rates. This is the first report on the enantioselective reduction of acetophenone by D. hansenii P1 from pastırma, a fermented Turkish meat product. The preparative scale asymmetric bio reduction of 3-methoxy acetophenone 1g by D. hansenii P1 gave (R)-1-(3-methoxyphenyl) ethanol 2g 82% yield, and >99% enantiomeric excess. Compound 2g can be used for the synthesis of (+)-NPS-R-568 [3-(2-chlorophenyl)-N-[(1R)-1-(3-methoxyphenly) ethyl] propan-1-amine] which have a great potential for the treatment of primary and secondary hyper-parathyroidism. In addition, D. hansenii P1 successfully reduced acetophenone derivatives. This study showed that this yeast can be used industrially to produce enantiomerically pure chiral secondary alcohols, which can be easily converted to different functional groups. © 2017 Informa UK Limited, trading as Taylor & Francis Group.en_US
dc.identifier.doi10.1080/10242422.2017.1348500
dc.identifier.endpage371
dc.identifier.issn1024-2422
dc.identifier.issue5
dc.identifier.scopus2-s2.0-85023160194en_US
dc.identifier.scopusqualityQ3en_US
dc.identifier.startpage363
dc.identifier.urihttps://dx.doi.org/10.1080/10242422.2017.1348500
dc.identifier.urihttps://hdl.handle.net/20.500.12403/468
dc.identifier.volume35
dc.identifier.wosWOS:000417422500006en_US
dc.identifier.wosqualityQ4en_US
dc.indekslendigikaynakWeb of Scienceen_US
dc.indekslendigikaynakScopusen_US
dc.language.isoenen_US
dc.publisherTaylor and Francis Ltd
dc.relation.ispartofBiocatalysis and Biotransformationen_US
dc.relation.publicationcategoryMakale - Uluslararası Hakemli Dergi - Kurum Öğretim Elemanıen_US
dc.rightsinfo:eu-repo/semantics/closedAccessen_US
dc.subjectBio reduction: asymmetric reduction
dc.subjectbio transformations
dc.subjectDebaryomyces hansenii
dc.subjectwhole yeast cells
dc.subjectAmorphous alloys
dc.subjectBioactivity
dc.subjectBiocatalysts
dc.subjectCondensation reactions
dc.subjectEnantiomers
dc.subjectEthanol
dc.subjectYeast
dc.subjectAsymmetric reduction
dc.subjectBiologically active compounds
dc.subjectChiral secondary alcohols
dc.subjectDebaryomyces hansenii
dc.subjectEnantiomeric excess
dc.subjectEnantioselective reduction
dc.subjectOptimized conditions
dc.subjectYeast cell
dc.subjectKetones
dc.subject1 (2 bromophenyl)ethanol
dc.subject1 (2 chlorophenyl)ethanol
dc.subject1 (2 methoxyphenyl)ethanol
dc.subject1 (2 nitrophenyl)ethanol
dc.subject1 (3 chlorophenyl)ethanol
dc.subject1 (3 methoxyphenyl)ethanol
dc.subject1 (4 biphenyl)ethanol
dc.subject1 (4 bromophenyl)ethanol
dc.subject1 (4 chlorophenyl)ethanol
dc.subject1 (4 methoxyphenyl)ethanol
dc.subject1 (4 nitrophenyl)ethanol
dc.subject1 (4 tolyl)ethanol
dc.subject1 phenylethanol
dc.subjectacetophenone derivative
dc.subjectalcohol derivative
dc.subjectketone derivative
dc.subjectnatural product
dc.subjectunclassified drug
dc.subjectArticle
dc.subjectasymmetric synthesis
dc.subjectbiocatalyst
dc.subjectcarbon nuclear magnetic resonance
dc.subjectchirality
dc.subjectDebaryomyces hansenii
dc.subjectdrug synthesis
dc.subjectenantiomer
dc.subjectenantioselectivity
dc.subjectfermentation
dc.subjectflow rate
dc.subjectfungal cell culture
dc.subjectfungal strain
dc.subjectfungus isolation
dc.subjectHanseniaspora guilliermondii
dc.subjecthigh performance liquid chromatography
dc.subjectnonhuman
dc.subjectprimary hyperparathyroidism
dc.subjectprocess optimization
dc.subjectproton nuclear magnetic resonance
dc.subjectreduction (chemistry)
dc.subjectretention time
dc.subjectSaccharomyces cerevisiae
dc.subjectsecondary hyperparathyroidism
dc.subjectBio reduction: asymmetric reduction
dc.subjectbio transformations
dc.subjectDebaryomyces hansenii
dc.subjectwhole yeast cells
dc.subjectAmorphous alloys
dc.subjectBioactivity
dc.subjectBiocatalysts
dc.subjectCondensation reactions
dc.subjectEnantiomers
dc.subjectEthanol
dc.subjectYeast
dc.subjectAsymmetric reduction
dc.subjectBiologically active compounds
dc.subjectChiral secondary alcohols
dc.subjectDebaryomyces hansenii
dc.subjectEnantiomeric excess
dc.subjectEnantioselective reduction
dc.subjectOptimized conditions
dc.subjectYeast cell
dc.subjectKetones
dc.subject1 (2 bromophenyl)ethanol
dc.subject1 (2 chlorophenyl)ethanol
dc.subject1 (2 methoxyphenyl)ethanol
dc.subject1 (2 nitrophenyl)ethanol
dc.subject1 (3 chlorophenyl)ethanol
dc.subject1 (3 methoxyphenyl)ethanol
dc.subject1 (4 biphenyl)ethanol
dc.subject1 (4 bromophenyl)ethanol
dc.subject1 (4 chlorophenyl)ethanol
dc.subject1 (4 methoxyphenyl)ethanol
dc.subject1 (4 nitrophenyl)ethanol
dc.subject1 (4 tolyl)ethanol
dc.subject1 phenylethanol
dc.subjectacetophenone derivative
dc.subjectalcohol derivative
dc.subjectketone derivative
dc.subjectnatural product
dc.subjectunclassified drug
dc.subjectArticle
dc.subjectasymmetric synthesis
dc.subjectbiocatalyst
dc.subjectcarbon nuclear magnetic resonance
dc.subjectchirality
dc.subjectDebaryomyces hansenii
dc.subjectdrug synthesis
dc.subjectenantiomer
dc.subjectenantioselectivity
dc.subjectfermentation
dc.subjectflow rate
dc.subjectfungal cell culture
dc.subjectfungal strain
dc.subjectfungus isolation
dc.subjectHanseniaspora guilliermondii
dc.subjecthigh performance liquid chromatography
dc.subjectnonhuman
dc.subjectprimary hyperparathyroidism
dc.subjectprocess optimization
dc.subjectproton nuclear magnetic resonance
dc.subjectreduction (chemistry)
dc.subjectretention time
dc.subjectSaccharomyces cerevisiae
dc.subjectsecondary hyperparathyroidism
dc.titleDebaryomyces hansenii as a new biocatalyst in the asymmetric reduction of substituted acetophenonesen_US
dc.typeArticleen_US

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