Bio-catalytic asymmetric synthesis of ?-adrenergic receptor blocker precursor: (R)-2-bromo-1-(naphthalen-2-yl)ethanol

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dc.authoridKalay, Erbay/0000-0002-4656-8254
dc.contributor.authorTasdemir, Volkan
dc.contributor.authorKalay, Erbay
dc.contributor.authorDertli, Enes
dc.contributor.authorSahin, Engin
dc.date.accessioned2024-10-04T18:48:25Z
dc.date.available2024-10-04T18:48:25Z
dc.date.issued2020
dc.departmentBayburt Üniversitesien_US
dc.description.abstractAromatic alpha-halohydrins, particularly 2-haloethanols as significant precursor of drugs, can easily be converted to chiral beta-adrenergic receptor blockers. Eight strains of Lactobacillus curvatus were tested as biocatalysts for asymmetric reduction of 2-bromo-1-(naphthalen-2-yl)ethanone 1 to 2-bromo-1- (naphthalen-2-yl) ethanol 2. The parameters of the bioreduction were optimized using L. curvatus N4, the best biocatalyst found. As a result, (R)-2-bromo-1-(naphthalen-2-yl)ethanol 2, which can be beta-adrenergic receptor blocker precursor, was produced for the first time in high yield and enantiomerically pure form using biocatalysts. Moreover, the gram scale synthesis was performed and 7.54 g of (R)-2 was synthesized as enantiopure form (enantiomeric excess >99%) in 48 h. The important advantages of this process are that it produces of (R)-2 for the first time in enantiopure form, in excellent yield and under environmentally friendly and moderate reaction conditions. This system is of the potential to be applied at a commercial scale.en_US
dc.identifier.doi10.1080/10242422.2020.1768245
dc.identifier.endpage444en_US
dc.identifier.issn1024-2422
dc.identifier.issn1029-2446
dc.identifier.issue6en_US
dc.identifier.scopus2-s2.0-85085629258en_US
dc.identifier.scopusqualityQ3en_US
dc.identifier.startpage438en_US
dc.identifier.urihttps://doi.org/10.1080/10242422.2020.1768245
dc.identifier.urihttp://hdl.handle.net/20.500.12403/3048
dc.identifier.volume38en_US
dc.identifier.wosWOS:000538739900001en_US
dc.identifier.wosqualityQ4en_US
dc.indekslendigikaynakWeb of Scienceen_US
dc.indekslendigikaynakScopusen_US
dc.language.isoenen_US
dc.publisherTaylor & Francis Ltden_US
dc.relation.ispartofBiocatalysis and Biotransformationen_US
dc.relation.publicationcategoryMakale - Uluslararası Hakemli Dergi - Kurum Öğretim Elemanıen_US
dc.rightsinfo:eu-repo/semantics/closedAccessen_US
dc.subjectChiral 2-haloethanolsen_US
dc.subjectbiocatalystsen_US
dc.subjectasymmetric reductionen_US
dc.subject(R)-2-bromo-1-(naphthalen-2-yl)ethanolen_US
dc.subjectLactobacillus curvatusen_US
dc.titleBio-catalytic asymmetric synthesis of ?-adrenergic receptor blocker precursor: (R)-2-bromo-1-(naphthalen-2-yl)ethanolen_US
dc.typeArticleen_US

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