Candida zeylanoides as whole-cell biocatalyst to perform asymmetric bioreduction of benzophenone derivatives

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Özet

Candida zeylanoides P1 was investigated as whole cell biocatalyst for the bioreduction of biaryl prochiral ketones into chiral carbinols, which can be used as pharmaceutical intermediate. Bioreduction of different biaryl ketones was carried out to their corresponding chiral biaryl carbinols such as (S)-(4-chlorophenyl) (phenyl) methanol (2a), which can be used in the synthesis of L-cloperastine drug, with antitussive, antiepidemic activity and bronchial musculature relaxant characteristics, in gram scale, enantiopure form (>99%) and excellent yields. The selectivity of C. zeylanoides P1 in enantioselective reduction of biaryl ketones was not affected by the steric and electronic effects of substrates. The current method demonstrates an encouraging green chemistry approach for the production of biaryl secondary chiral alcohols of pharmaceutical importance in mild, inexpensive and environmentally friendly process. The present study has many benefits since this yeast biocatalyst were successfully applied bioreduction of structurally bulky prochiral substrates, which cannot be reducted by chemical catalysis.

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dc.contributor.authorŞahin, Engin
dc.date.accessioned2026-10-29T19:09:15.200190808Z
dc.date.available2026-10-29T19:09:15.200190808Z
dc.date.issued2020
dc.description.abstractCandida zeylanoides P1 was investigated as whole cell biocatalyst for the bioreduction of biaryl prochiral ketones into chiral carbinols, which can be used as pharmaceutical intermediate. Bioreduction of different biaryl ketones was carried out to their corresponding chiral biaryl carbinols such as (S)-(4-chlorophenyl) (phenyl) methanol (2a), which can be used in the synthesis of L-cloperastine drug, with antitussive, antiepidemic activity and bronchial musculature relaxant characteristics, in gram scale, enantiopure form (>99%) and excellent yields. The selectivity of C. zeylanoides P1 in enantioselective reduction of biaryl ketones was not affected by the steric and electronic effects of substrates. The current method demonstrates an encouraging green chemistry approach for the production of biaryl secondary chiral alcohols of pharmaceutical importance in mild, inexpensive and environmentally friendly process. The present study has many benefits since this yeast biocatalyst were successfully applied bioreduction of structurally bulky prochiral substrates, which cannot be reducted by chemical catalysis.
dc.description.sponsorshipBayburt Üniversitesi, BÜ
dc.identifier.doi10.1080/00397911.2019.1710213
dc.identifier.eissn1532-2432
dc.identifier.endpage619
dc.identifier.issn0039-7911
dc.identifier.issue4
dc.identifier.scopus2-s2.0-85078615251
dc.identifier.startpage612
dc.identifier.urihttps://rdlopen.rawdatalibrary.net/r/bayburt/12155
dc.identifier.volume50
dc.identifier.wosWOS:000506571000001
dc.language.isoen
dc.publisherTaylor and Francis Inc.
dc.relation.ispartofSynthetic Communications
dc.rightsinfo:eu-repo/semantics/closedAccess
dc.subject(S)-(4-chlorophenyl) (phenyl) methanol
dc.subjectCandida zeylanoides
dc.subjectchiral benzophenone carbinols
dc.subjectChirality
dc.subjectenantioselective reduction
dc.subject.classificationChemistry, Organic
dc.subject.classificationChemistry
dc.subject.otherbenzophenone derivative
dc.subject.otherketone derivative
dc.subject.othermethanol
dc.subject.otherArticle
dc.subject.otherbiocatalyst
dc.subject.otherCandida zeylanoides
dc.subject.otherchirality
dc.subject.otherdrug synthesis
dc.subject.otherenantioselectivity
dc.subject.othergreen chemistry
dc.subject.othernonhuman
dc.subject.otherreduction (chemistry)
dc.titleCandida zeylanoides as whole-cell biocatalyst to perform asymmetric bioreduction of benzophenone derivatives
dc.typeArticle
rdl.citation.openalex10
rdl.citation.scopus10
rdl.citation.wos9
rdl.oa.statusclosed
rdl.scopus.quartileQ4
rdl.source.indexSCOPUS
rdl.source.indexWOS
rdl.wos.indexScience Citation Index Expanded (SCI-EXPANDED)