Production of enantiopure chiral aryl heteroaryl carbinols using whole-cell Lactobacillus paracasei biotransformation

Küçük Resim Yok

Tarih

2020

Dergi Başlığı

Dergi ISSN

Cilt Başlığı

Yayıncı

Taylor & Francis Inc

Erişim Hakkı

info:eu-repo/semantics/closedAccess

Özet

Aryl and heteroaryl chiral carbinols are useful precursors in the synthesis of drugs. Lactobacillus paracasei BD87E6, which is obtained from a cereal based fermented beverage, was investigated as whole cell biocatalyst for the bioreduction of different ketones (including aromatic, hetero-aromatic and fused bicyclic ketone) into chiral carbinols, which can be used as a pharmaceutical intermediate. The study shows that bioreduction of aryl, heteroaryl and fused bicyclic ketone (1-5) to their corresponding chiral carbinols (1a-5a) in excellent enantioselectivity (>99%) with high yields. This study gave the first example for an enantiopure production of (S)-6-chlorochroman-4-ol (3a), which has many antioxidant activity, by a biological method. For asymmetric bioreduction of other prochiral ketones, these results open way to use of L. paracasei BD87E6 as biocatalysts. Also, the present process shows a hopeful and alternative green synthesis for the production of enantiopure carbinols in a mild, inexpensive and environmentally friendly process.

Açıklama

Anahtar Kelimeler

Biotransformation, chiral heteroaryl carbinol, enantioselective bioreduction, (S)-6-chlorochroman-4-ol, whole-cell biocatalyst

Kaynak

Synthetic Communications

WoS Q Değeri

Q3

Scopus Q Değeri

Q3

Cilt

50

Sayı

4

Künye