img
Biocatalytic asymmetric synthesis of (R)-1-tetralol using Lactobacillus paracasei BD101     
Yazarlar
Doç. Dr. Erbay KALAY Doç. Dr. Erbay KALAY
Kafkas Üniversitesi, Türkiye
Engin Şahin
Bayburt Üniversitesi, Türkiye
Özet
Asymmetric bioreduction of ketones is a fundamental process in the production of organic molecules. Compounds containing tetralone rings are found in the structure of many biologically active and pharmaceutical molecules. Biocatalytic reduction of ketones is one of the most promising and significant routes to prepare optically active alcohols. In this study, the reductive capacity of Lactobacillus paracasei BD101 was investigated as whole-cell biocatalyst in the enantioselective reduction of 1-tetralone (1). In biocatalytic reduction reactions, the conversion of the substrate and the enantiomeric excess (ee) of the product are significantly affected by optimization parameters such as temperature, agitation rate, pH, and incubation time. Effects of these parameters on ee and conversion were investigated comprehensively. (R)-1-tetralol ((R)-2), which can be used to treat disorder such as obsessive compulsive, post-traumatic stress, premenstrual dysphoric, and social anxiety, was manufactured in enantiopure form, high yield and gram-scale, using whole-cell biocatalysts of L. paracasei BD101. The 7.04 g of (R)-2 was obtained in optically pure form with 95% yield. Also, to our knowledge, this is the first report on production of (R)-2 using whole-cell biocatalyst in excellent yield, conversion, enantiopure form and gram scale. This is a clean, eco-friendly and cheap method for the synthesis of (R)-2 compared with chemical catalyst.
Anahtar Kelimeler
(R)‐ | 1‐ | tetralol | chirality | drug scaffold | Lactobacillus paracasei BD101 | whole‐ | cell biocatalysts
Makale Türü Özgün Makale
Makale Alt Türü SSCI, AHCI, SCI, SCI-Exp dergilerinde yayımlanan tam makale
Dergi Adı CHIRALITY
Dergi ISSN 0899-0042
Dergi Tarandığı Indeksler SCI-Expanded
Dergi Grubu Q3
Makale Dili İngilizce
Basım Tarihi 08-2021
Cilt No 33
Sayı 8
Sayfalar 447 / 453
Doi Numarası 10.1002/chir.23318
Makale Linki https://onlinelibrary.wiley.com/doi/10.1002/chir.23318