First green synthesis of (R)-2-methyl-1-phenylpropan-1-ol using whole-cell Lactobacillus paracasei BD101 biotransformation

MakaleYalnız künyeScopus SJRQ3

Özet

Green chemistry includes a novel process in the production of drugs precursors and biological active molecules using biocatalysts, so reducing the threats for human sanitary and ecological pollutions. Asymmetric bioreduction of prochiral ketones by biocatalysts is one of the best prevalent used methods in synthetic organic chemistry due to the production of enantiopure chiral carbinols. This study emphasizes the application biocatalyst L paracasei BD101 for enantioselective bioreduction of 2-methyl-1-phenylpropan-1-one ketone, which contain branched alkyl chain, to (R)-2-methyl-1-phenylpropan-1-ol ((R)-2) in high yields and excellent enantiomeric excess (>99%). The scale-up production was performed, and 4.61 g of (R)-2 in enantiopure form was synthesized. L paracasei BD101 was proved to be a substantial biocatalyst in asymmetric bioreduction of a ketone which contains a branched alkyl chain. There is not any work in the literature similar to our study. Hence, it is important to work on filling this gap. This study is the first example for an enantiopure synthesis of (R)-2 by a biocatalyst. The new green method was developed for bioreduction of bulky ketones, which contains a branched alkyl chain, and it approves the synthesis of novel chiral carbinols in an easy, cheap, and environmentally friendly condition using L paracasei BD101.

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dc.contributor.authorŞahin, Engin
dc.date.accessioned2026-10-29T19:09:09.901007159Z
dc.date.available2026-10-29T19:09:09.901007159Z
dc.date.issued2020
dc.description.abstractGreen chemistry includes a novel process in the production of drugs precursors and biological active molecules using biocatalysts, so reducing the threats for human sanitary and ecological pollutions. Asymmetric bioreduction of prochiral ketones by biocatalysts is one of the best prevalent used methods in synthetic organic chemistry due to the production of enantiopure chiral carbinols. This study emphasizes the application biocatalyst L paracasei BD101 for enantioselective bioreduction of 2-methyl-1-phenylpropan-1-one ketone, which contain branched alkyl chain, to (R)-2-methyl-1-phenylpropan-1-ol ((R)-2) in high yields and excellent enantiomeric excess (>99%). The scale-up production was performed, and 4.61 g of (R)-2 in enantiopure form was synthesized. L paracasei BD101 was proved to be a substantial biocatalyst in asymmetric bioreduction of a ketone which contains a branched alkyl chain. There is not any work in the literature similar to our study. Hence, it is important to work on filling this gap. This study is the first example for an enantiopure synthesis of (R)-2 by a biocatalyst. The new green method was developed for bioreduction of bulky ketones, which contains a branched alkyl chain, and it approves the synthesis of novel chiral carbinols in an easy, cheap, and environmentally friendly condition using L paracasei BD101.
dc.identifier.doi10.1080/10242422.2019.1698554
dc.identifier.eissn1029-2446
dc.identifier.endpage143
dc.identifier.issn1024-2422
dc.identifier.issue2
dc.identifier.scopus2-s2.0-85076435619
dc.identifier.startpage138
dc.identifier.urihttps://rdlopen.rawdatalibrary.net/r/bayburt/12078
dc.identifier.volume38
dc.identifier.wosWOS:000501039100001
dc.language.isoen
dc.publisherTaylor and Francis Ltd
dc.relation.ispartofBiocatalysis and Biotransformation
dc.rightsinfo:eu-repo/semantics/closedAccess
dc.subject(R)-2-methyl-1-phenylpropan-1-ol
dc.subjectbiocatalyst
dc.subjectChirality
dc.subjectenantioselective bioreduction
dc.subjectgreen synthesis
dc.subject.classificationBiochemistry & Molecular Biology
dc.subject.classificationBiotechnology & Applied Microbiology
dc.subject.otherBiocatalysts
dc.subject.otherChirality
dc.subject.otherEnantioselectivity
dc.subject.otherEnzymes
dc.subject.otherKetones
dc.subject.otherMethanol
dc.subject.other2 methyl 1 phenylpropan 1 ol
dc.subject.other2 methyl 1 phenylpropan 1 one ketone
dc.subject.otheralkane derivative
dc.subject.otheralkyl group
dc.subject.otherketone derivative
dc.subject.othermethanol derivative
dc.subject.otherunclassified drug
dc.subject.other(R)-2-methyl-1-phenylpropan-1-ol
dc.subject.otherAsymmetric bioreduction
dc.subject.otherBio reductions
dc.subject.otherEcological pollutions
dc.subject.otherEnantiomeric excess
dc.subject.otherEnvironmentally friendly condition
dc.subject.otherGreen synthesis
dc.subject.otherSynthetic organic chemistry
dc.subject.otherArticle
dc.subject.otherasymmetric synthesis
dc.subject.otherbacterial strain
dc.subject.otherbiocatalysis
dc.subject.otherbiocatalyst
dc.subject.otherbiotransformation
dc.subject.otherenantiomer
dc.subject.othergreen chemistry
dc.subject.otherLactobacillus paracasei
dc.subject.othernonhuman
dc.subject.otherprecursor
dc.subject.otherreduction (chemistry)
dc.subject.otherscale up
dc.subject.otherwhole cell
dc.subject.otherStereochemistry
dc.titleFirst green synthesis of (R)-2-methyl-1-phenylpropan-1-ol using whole-cell Lactobacillus paracasei BD101 biotransformation
dc.typeArticle
rdl.citation.openalex10
rdl.citation.scopus10
rdl.citation.wos9
rdl.oa.statusclosed
rdl.scopus.quartileQ3
rdl.source.indexSCOPUS
rdl.source.indexWOS
rdl.wos.indexScience Citation Index Expanded (SCI-EXPANDED)