Whole cell application of Lactobacillus paracasei BD101 to produce enantiomerically pure (S)-cyclohexyl(phenyl)methanol

MakaleAçık ErişimScopus SJRQ3

Özet

In this study, a total of 10 bacterial strains were screened for their ability to reduce cyclohexyl(phenyl)methanone 1 to its corresponding alcohol. Among these strains, Lactobacillus paracasei BD101 was found to be the most successful biocatalyst to reduce the ketones to the corresponding alcohols. The reaction conditions were systematically optimized for the reducing agent L paracasei BD101, which showed high enantioselectivity and conversion for the bioreduction. The preparative scale asymmetric reduction of cyclohexyl(phenyl)methanone (1) by L paracasei BD101 gave (S)-cyclohexyl(phenyl)methanol (2) with 92% yield and >99% enantiomeric excess. The preparative scale study was carried out, and a total of 5.602 g of (S)-cyclohexyl(phenyl)methanol in high enantiomerically pure form (>99% enantiomeric excess) was produced. L paracasei BD101 has been shown to be an important biocatalyst in asymmetric reduction of bulky substrates. This study demonstrates the first example of the effective synthesis of (S)-cyclohexyl(phenyl)methanol by the L paracasei BD101 as a biocatalyst in preparative scale.

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RDL Kalıcı Bağlantı (PID)
https://rdlopen.rawdatalibrary.net/r/bayburt/12315Resmi atıflarda kullanılan kalıcı adres
DOI
https://doi.org/10.1002/chir.23048Yayıncı resmi DOI adresi
İndeks kayıtları
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Atıflar
Scopus
39
WoS
37
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Tam Kayıt
AlanDeğerDil
dc.contributor.authorŞahin, Engin
dc.contributor.authorSerencam, Hüseyin
dc.contributor.authorDertli, Enes
dc.date.accessioned2026-10-29T19:09:26.015193023Z
dc.date.available2026-10-29T19:09:26.015193023Z
dc.date.issued2019
dc.description.abstractIn this study, a total of 10 bacterial strains were screened for their ability to reduce cyclohexyl(phenyl)methanone 1 to its corresponding alcohol. Among these strains, Lactobacillus paracasei BD101 was found to be the most successful biocatalyst to reduce the ketones to the corresponding alcohols. The reaction conditions were systematically optimized for the reducing agent L paracasei BD101, which showed high enantioselectivity and conversion for the bioreduction. The preparative scale asymmetric reduction of cyclohexyl(phenyl)methanone (1) by L paracasei BD101 gave (S)-cyclohexyl(phenyl)methanol (2) with 92% yield and >99% enantiomeric excess. The preparative scale study was carried out, and a total of 5.602 g of (S)-cyclohexyl(phenyl)methanol in high enantiomerically pure form (>99% enantiomeric excess) was produced. L paracasei BD101 has been shown to be an important biocatalyst in asymmetric reduction of bulky substrates. This study demonstrates the first example of the effective synthesis of (S)-cyclohexyl(phenyl)methanol by the L paracasei BD101 as a biocatalyst in preparative scale.
dc.description.sponsorshipBayburt University
dc.identifier.doi10.1002/chir.23048
dc.identifier.eissn1520-636X
dc.identifier.endpage218
dc.identifier.issn0899-0042
dc.identifier.issue3
dc.identifier.pmid30633374
dc.identifier.scopus2-s2.0-85059887557
dc.identifier.startpage211
dc.identifier.urihttps://rdlopen.rawdatalibrary.net/r/bayburt/12315
dc.identifier.volume31
dc.identifier.wosWOS:000458827600006
dc.language.isoen
dc.publisherJohn Wiley and Sons Inc.
dc.relation.ispartofChirality
dc.rightsinfo:eu-repo/semantics/openAccess
dc.subjectasymmetric reduction
dc.subjectbiocatalyst
dc.subjectbiotransformations
dc.subjectchiral aryl methanols
dc.subjectenantioselectivity
dc.subject.classificationChemistry, Medicinal
dc.subject.classificationChemistry, Analytical
dc.subject.classificationChemistry, Organic
dc.subject.classificationPharmacology & Pharmacy
dc.subject.classificationChemistry
dc.subject.otheralcohol derivative
dc.subject.othercyclohexane derivative
dc.subject.otherketone derivative
dc.subject.othermethanol
dc.subject.otherphenyl group
dc.subject.otherreducing agent
dc.subject.otherbacterial cell
dc.subject.otherbacterial strain
dc.subject.otherbiocatalyst
dc.subject.otherbiotransformation
dc.subject.otherenantiomer
dc.subject.otherenantioselectivity
dc.subject.otherEnterococcus faecium
dc.subject.otherhigh performance liquid chromatography
dc.subject.otherincubation time
dc.subject.otherLactobacillus fermentum
dc.subject.otherLactobacillus paracasei
dc.subject.otherLactobacillus plantarum
dc.subject.otherLeuconostoc mesenteroides
dc.subject.othernonhuman
dc.subject.otherpH
dc.subject.otherpriority journal
dc.subject.otherreaction temperature
dc.subject.otherreduction (chemistry)
dc.subject.othershear stress
dc.subject.othersubstrate concentration
dc.subject.otherthin layer chromatography
dc.subject.otherWeissella
dc.subject.otherWeissella cibaria
dc.subject.otherWeissella paramesenteroides
dc.subject.otherwhole cell
dc.titleWhole cell application of Lactobacillus paracasei BD101 to produce enantiomerically pure (S)-cyclohexyl(phenyl)methanol
dc.typeArticle
rdl.citation.scopus39
rdl.citation.wos37
rdl.departmentDepartment of Food Engineering, Faculty of Engineering, Bayburt University, Bayburt, Turkey
rdl.oa.statusclosed
rdl.oa.statusgreen
rdl.oa.urlhttps://hdl.handle.net/20.500.12403/306
rdl.scopus.quartileQ3
rdl.source.indexSCOPUS
rdl.source.indexWOS
rdl.source.indexPUBMED
rdl.wos.indexScience Citation Index Expanded (SCI-EXPANDED)