Biocatalytic asymmetric synthesis of (S)-1-indanol using Lactobacillus paracasei BD71

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Özet

Enantiopure benzo-fused cyclic alcohols have been used as a building block of a drug for Parkinson’s disease. Biocatalytic reduction of ketones is one of the most promising and significant routes to prepare optically active alcohols. In this study, the reductive capacity of seven lactic acid bacteria (LAB) strains were investigated as whole-cell biocatalyst in the enantioselective reduction of 1-indanone (1). Lactobacillus paracasei BD71 was found to have the best reductive capacity. Effects of different parameters such as pH, incubation time, agitation speed and temperature, on enantiomeric excess (ee) and conversion were investigated in a bioconversion. (S)-1-indanol ((S)-2) could be used as precursor for the synthesis of rasagiline mesylate TVP1012 for the therapy of Parkinson’s illness. It was produced in gram-scale (5.24 g), high yield (93%) and enantiomerically pure form using L. paracasei BD71 whole-cell biocatalysts. Also, to our knowledge, this is the first report on production of (S)-2 using whole-cell catalyst in enantiopure form, excellent yield, conversion and gram scale. This is a cheap, clean and eco-friendly process for production of (S)-2 compared to chemical processes.

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AlanDeğerDil
dc.contributor.authorKalay, Erbay
dc.contributor.authorDertli, Enes
dc.contributor.authorŞahin, Engin
dc.date.accessioned2026-10-29T19:09:06.127408860Z
dc.date.available2026-10-29T19:09:06.127408860Z
dc.date.issued2022
dc.description.abstractEnantiopure benzo-fused cyclic alcohols have been used as a building block of a drug for Parkinson’s disease. Biocatalytic reduction of ketones is one of the most promising and significant routes to prepare optically active alcohols. In this study, the reductive capacity of seven lactic acid bacteria (LAB) strains were investigated as whole-cell biocatalyst in the enantioselective reduction of 1-indanone (1). Lactobacillus paracasei BD71 was found to have the best reductive capacity. Effects of different parameters such as pH, incubation time, agitation speed and temperature, on enantiomeric excess (ee) and conversion were investigated in a bioconversion. (S)-1-indanol ((S)-2) could be used as precursor for the synthesis of rasagiline mesylate TVP1012 for the therapy of Parkinson’s illness. It was produced in gram-scale (5.24 g), high yield (93%) and enantiomerically pure form using L. paracasei BD71 whole-cell biocatalysts. Also, to our knowledge, this is the first report on production of (S)-2 using whole-cell catalyst in enantiopure form, excellent yield, conversion and gram scale. This is a cheap, clean and eco-friendly process for production of (S)-2 compared to chemical processes.
dc.identifier.doi10.1080/10242422.2021.2004133
dc.identifier.eissn1029-2446
dc.identifier.endpage392
dc.identifier.issn1024-2422
dc.identifier.issue5
dc.identifier.scopus2-s2.0-85119347087
dc.identifier.startpage386
dc.identifier.urihttps://rdlopen.rawdatalibrary.net/r/bayburt/12031
dc.identifier.volume40
dc.identifier.wosWOS:000719228000001
dc.language.isoen
dc.publisherTaylor and Francis Ltd.
dc.relation.ispartofBiocatalysis and Biotransformation
dc.rightsinfo:eu-repo/semantics/closedAccess
dc.subject(S)-1-indanol
dc.subjectBiotransformation
dc.subjectLactobacillus paracasei BD71
dc.subjectParkinson’s drug precursor
dc.subjectwhole-cell biocatalysts
dc.subject.classificationBiochemistry & Molecular Biology
dc.subject.classificationBiotechnology & Applied Microbiology
dc.subject.otherBacilli
dc.subject.otherCells
dc.subject.otherCytology
dc.subject.otherEnantiomers
dc.subject.otherEnzymes
dc.subject.otherKetones
dc.subject.other1 indanone
dc.subject.otherketone
dc.subject.otherrasagiline
dc.subject.otherunclassified drug
dc.subject.other(S)-1-indanol
dc.subject.otherAsymmetric synthesis
dc.subject.otherBuilding blockes
dc.subject.otherCyclic alcohols
dc.subject.otherEnantiopure
dc.subject.otherGram scale
dc.subject.otherIndanol
dc.subject.otherLactobacillus paracasei bd71
dc.subject.otherParkinson’s drug precursor
dc.subject.otherWhole cell biocatalysts
dc.subject.otheragitation
dc.subject.otherArticle
dc.subject.otherbacterial strain
dc.subject.otherbacterium culture
dc.subject.otherbacterium isolation
dc.subject.otherbiocatalysis
dc.subject.otherbiotransformation
dc.subject.othercarbon nuclear magnetic resonance
dc.subject.otherchemical phenomena
dc.subject.otherchiral chromatography
dc.subject.othercolumn chromatography
dc.subject.othercontrolled study
dc.subject.otherdrug structure
dc.subject.otherenantiomeric excess
dc.subject.otherenantioselectivity
dc.subject.otherEnterococcus faecium
dc.subject.otherenzyme activity
dc.subject.otherflow rate
dc.subject.otherhigh performance liquid chromatography
dc.subject.otherincubation time
dc.subject.otherlactic acid bacterium
dc.subject.otherLactobacillus fermentum
dc.subject.otherLactobacillus paracasei
dc.subject.otherLactobacillus plantarum
dc.subject.othernonhuman
dc.subject.otherpH
dc.subject.otherproton nuclear magnetic resonance
dc.subject.othertemperature
dc.subject.otherthin layer chromatography
dc.subject.otherLactic acid
dc.titleBiocatalytic asymmetric synthesis of (S)-1-indanol using Lactobacillus paracasei BD71
dc.typeArticle
rdl.citation.openalex6
rdl.citation.scopus6
rdl.citation.wos6
rdl.oa.statusclosed
rdl.scopus.quartileQ3
rdl.sdgSDG03
rdl.source.indexSCOPUS
rdl.source.indexWOS
rdl.wos.indexScience Citation Index Expanded (SCI-EXPANDED)