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oai:bayburt-rdlopen.rawdatalibrary.net:bayburt/119592026-10-29T19:42:03Zopenairedrivercom_bayburt_10000col_bayburt_10001com_bayburt_10007col_bayburt_10225

Synthesis of enantiopure (S)-6-chlorochroman-4-ol using whole-cell Lactobacillus paracasei biotransformationŞahin, Engin(S)-6-chlorochroman-4-olasymmetric reductionbiotransformationchiralitygreen synthesisChromane, which has a fused cyclic structure, is a significant molecule that can be found in the structure of many important compounds. Lactobacillus paracasei BD101 was demonstrated as whole-cell biocatalyst for the synthesis of (S)-6-chlorochroman-4-ol with immense enantioselectivity. The conditions of asymmetric reduction were optimized one factor by one factor using L paracasei BD101 to achieve enantiomerically pure product and complete conversion. Using these obtained optimization conditions, asymmetric reduction of 6-chlorochroman-4-one was performed under environmentally friendly conditions; 6-chlorochroman-4-one, having a fused cyclic structure as previously noted to be difficult to asymmetric reduction with biocatalysts, was enantiomerically reduced to (S)-6-chlorochroman-4-ol with an enantiomeric excess >99% on a high gram scale. This study is the first example in the literature for the enantiopure synthesis of (S)-6-chlorochroman-4-ol using a biocatalyst. Also notably, the optical purity of (S)-6-chlorochroman-4-ol obtained in this study through asymmetric bioreduction using whole-cell biocatalyst is the highest value in the literature. In this study, (S)-6-chlorochroman-4-ol was produced on a gram scale by an easy, inexpensive, and environmentally friendly method, which has shown the production of valuable chiral precursors for drug synthesis and other industrial applications. This study provides a convenient method for the production of (S)-6-chlorochroman-4-ol, which can meet the industrial green production demand of this chiral secondary alcohol.John Wiley and Sons Inc.2020Articlehttps://rdlopen.rawdatalibrary.net/r/bayburt/11959https://doi.org/10.1002/chir.231770899-0042enChiralityinfo:eu-repo/semantics/openAccessinfo:eu-repo/semantics/articlehttps://bayburt-rdlopen.rawdatalibrary.net/tr/items/bayburt/11959