Biocatalyzed Enantiomerically Pure Production of (S)?Phenyl(thiophen?2?yl)methanol

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dc.authorid0000-0002-3723-1705en_US
dc.contributor.authorŞahin, Engin
dc.contributor.authorDertli, Enes
dc.date.accessioned2020-11-25T19:40:40Z
dc.date.available2020-11-25T19:40:40Z
dc.date.issued2019en_US
dc.departmentFakülteler, Sağlık Bilimleri Fakültesi, Beslenme ve Diyetetik Bölümüen_US
dc.description.abstractChiral aryl heteroaryl methanols are important precursors for the synthesis of pharmaceutically important molecules. The aims of this study were to use a biocatalyst that could efficiently bioreduce phenyl(thiophen‐2‐yl)methanone 1 to (S)‐phenyl(thiophen‐2‐yl)methanol 2, to identify the impact of the physicochemical factors that might affect the bioreduction by the biocatalyst, and to obtain multigram production of aryl heteroaryl secondary alcohol 2 with the biocatalyst under optimized conditions. Over the years, the (S)‐phenyl(thiophen‐2‐yl)methanol was synthesized on a small scale using a chemical catalyst without its enantiomerically pure form. In this study, Lactobacillus paracasei BD101 was used for the asymmetric reduction of phenyl(thiophen‐2‐yl)methanone to (S)‐phenyl(thiophen‐2‐yl)methanol in the large‐scale production. The asymmetric bioreduction conditions were systematically optimized, and the production of 3.77 g of (S)‐phenyl(thiophen‐2‐yl)methanol was carried out in enantiomerically pure form >99% enantiomeric excess (ee), >99% conversion, and 90% yield. This method obtained with this biocatalyst is a process that can be used industrially in terms of conversion, ee, and yield. This study provides guidance for the application of L. paracasei BD101 in the production of optically active aryl heteroaryl alcohols.en_US
dc.identifier.citationŞahin, E., & Dertli, E. (2019). Biocatalyzed Enantiomerically Pure Production of (S)‐Phenyl (thiophen‐2‐yl) methanol. Journal of Heterocyclic Chemistry, 56(10), 2884-2888.en_US
dc.identifier.doi10.1002/jhet.3681
dc.identifier.endpage2888en_US
dc.identifier.issue10en_US
dc.identifier.scopus2-s2.0-85070854421en_US
dc.identifier.scopusqualityQ3en_US
dc.identifier.startpage2884en_US
dc.identifier.urihttps://onlinelibrary.wiley.com/doi/full/10.1002/jhet.3681?casa_token=IKh_QyLp_uoAAAAA%3AmccjIO_F-KWtiy4G2R5hj54qBQ7sVxUpxe_Y_KwEYXcZEgAaBt3x_tMfY2GYNNUHRBN3RmLv1TRyJN7T
dc.identifier.urihttps://hdl.handle.net/20.500.12403/2224
dc.identifier.volume56en_US
dc.identifier.wosWOS:000482368200001en_US
dc.identifier.wosqualityQ3en_US
dc.indekslendigikaynakWeb of Scienceen_US
dc.indekslendigikaynakScopusen_US
dc.language.isoenen_US
dc.publisherThe Journal of Heterocyclic Chemistryen_US
dc.relation.ispartofThe Journal of Heterocyclic Chemistryen_US
dc.relation.publicationcategoryMakale - Uluslararası Hakemli Dergi - Kurum Öğretim Elemanıen_US
dc.subjectChiralityen_US
dc.subjectBiotransformationen_US
dc.subjectasymmetric reductionen_US
dc.titleBiocatalyzed Enantiomerically Pure Production of (S)?Phenyl(thiophen?2?yl)methanolen_US
dc.typeArticleen_US

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