Production of (R)-1-(1,3-benzodioxol-5-yl)ethanol in high enantiomeric purity by Lactobacillus paracasei BD101

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dc.authorid37098938400
dc.contributor.authorŞahin E.
dc.date.accessioned20.04.201910:49:12
dc.date.accessioned2019-04-20T21:43:08Z
dc.date.available20.04.201910:49:12
dc.date.available2019-04-20T21:43:08Z
dc.date.issued2018
dc.departmentBayburt Üniversitesien_US
dc.description.abstractPiperonyl ring is found in a number of naturally occurring compounds and possesses enormous biological activities. There are many studies in the literature with compounds containing a piperonyl ring, but there are very few studies on the synthesis of chiral piperonyl carbinol. The objective of this study was to determine the microbial reduction ability of bacterial strains and to reveal the effects of different physicochemical parameters on this reduction ability. A total of 15 bacterial isolates were screened for their ability to reduce 1-(benzo[d][1,3]dioxol-5-yl) ethanone 1 to its corresponding alcohol. Among these isolates Lactobacillus paracasei BD101 was found to be the most successful biocatalyst to reduce the ketone containing piperonyl ring to the corresponding alcohol. 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 study was performed, and a total of 3.72 g of (R)-1-(1,3-benzodioxol-5-yl) ethanol in high enantiomeric form (>99% enantiomeric excess) was produced in a mild, cheap, and environment-friendly process. This study demonstrates that L paracasei BD101 can be used as a biocatalyst to obtain chiral carbinol with excellent yield and selectivity. © 2017 Wiley Periodicals, Inc.en_US
dc.identifier.doi10.1002/chir.22782
dc.identifier.endpage194
dc.identifier.issn0899-0042
dc.identifier.issue2
dc.identifier.pmid29110342en_US
dc.identifier.scopus2-s2.0-85040364625en_US
dc.identifier.scopusqualityQ3en_US
dc.identifier.startpage189
dc.identifier.urihttps://dx.doi.org/10.1002/chir.22782
dc.identifier.urihttps://hdl.handle.net/20.500.12403/408
dc.identifier.volume30
dc.identifier.wosWOS:000419687000008en_US
dc.identifier.wosqualityQ3en_US
dc.indekslendigikaynakWeb of Scienceen_US
dc.indekslendigikaynakScopusen_US
dc.indekslendigikaynakPubMeden_US
dc.language.isoenen_US
dc.publisherJohn Wiley and Sons Inc.
dc.relation.ispartofChiralityen_US
dc.relation.publicationcategoryMakale - Uluslararası Hakemli Dergi - Kurum Öğretim Elemanıen_US
dc.rightsinfo:eu-repo/semantics/closedAccessen_US
dc.subjectasymmetric reduction
dc.subjectbiocatalyst
dc.subjectbiotransformations
dc.subjectpiperonyl carbinol
dc.subjectpiperonyl ring
dc.subjectalcohol derivative
dc.subjectketone derivative
dc.subjectpipamperone
dc.subjectalcohol
dc.subjectbenzoxazole derivative
dc.subjectalcohol production
dc.subjectArticle
dc.subjectbacterial strain
dc.subjectbiocatalyst
dc.subjectenantiomer
dc.subjectenantioselectivity
dc.subjectLactobacillus paracasei
dc.subjectnonhuman
dc.subjectphysical chemistry
dc.subjectpriority journal
dc.subjectreduction (chemistry)
dc.subjectchemistry
dc.subjectLactobacillus paracasei
dc.subjectmetabolism
dc.subjectpH
dc.subjectstereoisomerism
dc.subjecttemperature
dc.subjectBenzoxazoles
dc.subjectEthanol
dc.subjectHydrogen-Ion Concentration
dc.subjectLactobacillus paracasei
dc.subjectStereoisomerism
dc.subjectTemperature
dc.subjectasymmetric reduction
dc.subjectbiocatalyst
dc.subjectbiotransformations
dc.subjectpiperonyl carbinol
dc.subjectpiperonyl ring
dc.subjectalcohol derivative
dc.subjectketone derivative
dc.subjectpipamperone
dc.subjectalcohol
dc.subjectbenzoxazole derivative
dc.subjectalcohol production
dc.subjectArticle
dc.subjectbacterial strain
dc.subjectbiocatalyst
dc.subjectenantiomer
dc.subjectenantioselectivity
dc.subjectLactobacillus paracasei
dc.subjectnonhuman
dc.subjectphysical chemistry
dc.subjectpriority journal
dc.subjectreduction (chemistry)
dc.subjectchemistry
dc.subjectLactobacillus paracasei
dc.subjectmetabolism
dc.subjectpH
dc.subjectstereoisomerism
dc.subjecttemperature
dc.subjectBenzoxazoles
dc.subjectEthanol
dc.subjectHydrogen-Ion Concentration
dc.subjectLactobacillus paracasei
dc.subjectStereoisomerism
dc.subjectTemperature
dc.titleProduction of (R)-1-(1,3-benzodioxol-5-yl)ethanol in high enantiomeric purity by Lactobacillus paracasei BD101en_US
dc.typeArticleen_US

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