Optimization of asymmetric reduction conditions of 2-bromo-1-(naphthalen-2-yl)ethanone by Enterococcus faecium BY48 biocatalyst with A-optimal design-embedded model

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dc.authoridOzdemir, Akin/0000-0002-1716-6694
dc.contributor.authorOzdemir, Akin
dc.contributor.authorSahin, Engin
dc.date.accessioned2024-10-04T18:52:33Z
dc.date.available2024-10-04T18:52:33Z
dc.date.issued2022
dc.departmentBayburt Üniversitesien_US
dc.description.abstractAromatic alpha-halohydrins, especially 2-haloethanols, which are a common pharmacological precursor, may be readily transformed to chiral beta-adrenergic receptor blockers. Studies including the synthesis of (S)-2-bromo-1-(naphthalen-2-yl)ethanol ((S)-2), an alpha-halohydrin, in high conversion, enantiomeric excess (ee), and yield by biocatalytic asymmetric reduction of 2-bromo-1-(naphthalen-2-yl)ethanone (1) are still insufficient. Moreover, asymmetric reduction of substrate 1 using a mathematical optimization method is not explored in the current literature. In this article, the four asymmetric bioreduction conditions, which are (1) pH, (2) temperature, (3) incubation period, and (4) agitation speed, of substrate 1 were optimized to obtain (S)-2 with A-optimal design-embedded model in the presence of Enterococcus faecium BY48. Optimum bioreduction conditions were determined by the A-optimal design-embedded model as follows: pH = 7, temperature = 25 degrees C, incubation period = 24 h, and agitation speed = 200 rpm. And then, it was suggested that (S)-2 could be obtained with 98.88% ee and 100% conversion rate (cr) under these optimum conditions. As a result of the experimental reaction performed under the optimization conditions suggested by the model, (S)-2 was obtained with 99% ee and 100% cr. The study revealed that E. faecium BY48 could be used as a biocatalyst in asymmetric reduction reactions. Also, the A-optimal design-embedded model could have the great potential to obtain the optimum asymmetric bioreduction conditions.en_US
dc.description.sponsorshipYildiz Technical Universityen_US
dc.description.sponsorshipYildiz Technical Universityen_US
dc.identifier.doi10.1002/chir.23430
dc.identifier.endpage806en_US
dc.identifier.issn0899-0042
dc.identifier.issn1520-636X
dc.identifier.issue5en_US
dc.identifier.pmid35218076en_US
dc.identifier.scopus2-s2.0-85125241769en_US
dc.identifier.scopusqualityQ3en_US
dc.identifier.startpage796en_US
dc.identifier.urihttps://doi.org/10.1002/chir.23430
dc.identifier.urihttp://hdl.handle.net/20.500.12403/3547
dc.identifier.volume34en_US
dc.identifier.wosWOS:000761178000001en_US
dc.identifier.wosqualityQ3en_US
dc.indekslendigikaynakWeb of Scienceen_US
dc.indekslendigikaynakScopusen_US
dc.indekslendigikaynakPubMeden_US
dc.language.isoenen_US
dc.publisherWileyen_US
dc.relation.ispartofChiralityen_US
dc.relation.publicationcategoryMakale - Uluslararası Hakemli Dergi - Kurum Öğretim Elemanıen_US
dc.rightsinfo:eu-repo/semantics/closedAccessen_US
dc.subject(S)-2-bromo-1-(naphthalen-2-yl)ethanolen_US
dc.subjectA-optimal designen_US
dc.subjectasymmetric bioreductionen_US
dc.subjectchiral halohydrinsen_US
dc.subjectoptimizationen_US
dc.subjectwhole-cell biocatalysten_US
dc.titleOptimization of asymmetric reduction conditions of 2-bromo-1-(naphthalen-2-yl)ethanone by Enterococcus faecium BY48 biocatalyst with A-optimal design-embedded modelen_US
dc.typeArticleen_US

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