Efficient bio-catalytic production of enentiopure (S)-(4-chlorophenyl) (phenyl)methanol as a drug precursor by using a novel rotatable composite design-based optimization strategy

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dc.contributor.authorTozlu, Nesrullah
dc.contributor.authorBulbul, Ali Savas
dc.contributor.authorOzdemir, Akin
dc.contributor.authorSahin, Engin
dc.date.accessioned2024-10-04T18:49:41Z
dc.date.available2024-10-04T18:49:41Z
dc.date.issued2023
dc.departmentBayburt Üniversitesien_US
dc.description.abstractAsymmetric bioreductions catalyzed by biocatalysts have demonstrated great promise in manufacturing chiral alcohols. On the other hand, the synthesis of (S)-(4-chlorophenyl)(phenyl)methanol ((S)-2), precursors of Lcloprastine and carbinoxamine, still presents considerable challenges due to the inadequate substrate quantity and production process. In this work, a novel rotatable composite design-based optimization technique was used with the Lactobacillus paracasei BD101 biocatalyst for the asymmetric reduction of (4-chlorophenyl)(phenyl) methanone (1). Optimization conditions of the reaction were determined by the proposed optimization strategy as: pH=5.85, temperature=37 degrees C, incubation time=71 h, and agitation speed=120 rpm. The reaction conversion and the product of enantiomeric excess (ee) were also predicted to be 97% and 99%, respectively. In the experimental study performed under the determined optimized conditions, (S)-2 was obtained with >99% ee, >99% conversion, and 97% yield. In addition, 1 with the amount of 15.166 g was completely converted to (S)-2 (14.85 g, 97% isolated yield) on a high-gram scale. Notice that the manufacture of (S)-2 on a gram scale utilizing a biocatalyst and an optimization technique is demonstrated in this work for the first time. Finally, an economical, effective, and environmentally friendly biocatalytic process for the biocatalytic synthesis of (S)-2, which have antitussive and antiemetic properties and relax the bronchial muscle, has been demonstrated by the novel rotatable composite design-based optimization method.en_US
dc.identifier.doi10.1016/j.mcat.2023.113404
dc.identifier.issn2468-8231
dc.identifier.scopus2-s2.0-85166278445en_US
dc.identifier.scopusqualityQ2en_US
dc.identifier.urihttps://doi.org/10.1016/j.mcat.2023.113404
dc.identifier.urihttp://hdl.handle.net/20.500.12403/3254
dc.identifier.volume547en_US
dc.identifier.wosWOS:001047298500001en_US
dc.identifier.wosqualityQ2en_US
dc.indekslendigikaynakWeb of Scienceen_US
dc.indekslendigikaynakScopusen_US
dc.language.isoenen_US
dc.publisherElsevieren_US
dc.relation.ispartofMolecular Catalysisen_US
dc.relation.publicationcategoryMakale - Uluslararası Hakemli Dergi - Kurum Öğretim Elemanıen_US
dc.rightsinfo:eu-repo/semantics/closedAccessen_US
dc.subjectBiocatalysisen_US
dc.subjectDrug precursoren_US
dc.subjectAsymmetric bioreductionen_US
dc.subjectGreen chemistryen_US
dc.subject(s)-(4-chlorophenyl)(phenyl)methanolen_US
dc.titleEfficient bio-catalytic production of enentiopure (S)-(4-chlorophenyl) (phenyl)methanol as a drug precursor by using a novel rotatable composite design-based optimization strategyen_US
dc.typeArticleen_US

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