Production of enantiomerically enriched chiral carbinols using Weissella paramesenteroides as a novel whole cell biocatalyst

Küçük Resim Yok

Tarih

2019

Dergi Başlığı

Dergi ISSN

Cilt Başlığı

Yayıncı

Biocatalysis and Biotransformation

Erişim Hakkı

Özet

In this study, four bacterial strains were tested for their ability to reduce acetophenones to its corresponding alcohol. Among these strains Weissella paramesenteroides N7 was found to be the most successful biocatalyst to reduce the ketones to the corresponding alcohols. The reaction conditions were systematically optimized for W. paramesenteroides N7 that resulted in high enantioselectivity and conversion rates for the bioreduction. The scale-up asymmetric reduction of 1-(4-methoxyphenyl) propan-1-one (1r) by W. paramesenteroides N7 gave (R)-1-(4-methoxyphenyl) propan-1-ol (2r) with 94% yield and >99% enantiomeric excess. This is the first report showing the synthesis of (R)-1-(4-methoxyphenyl) propan-1-ol (2r) in enantiopure form using a biocatalyst on a gram scale. The whole cell catalyzed the reductions of ketone substrates on the preparative scale, demonstrating that W. paramesenteroides N7 would be a valuable biocatalyst for the preparation of chiral aromatic alcohols of pharmaceutical interest as a promising and alternative green approach. Weissella paramesenteroides as a food originated yeast species is capable of bioreduction of prochiral ketones to secondary chiral alcohols in one enantiomeric form.

Açıklama

Anahtar Kelimeler

Weissella paramesenteroides N7, Biotransformation, Chirality

Kaynak

Biocatalysis and Biotransformation

WoS Q Değeri

Q3

Scopus Q Değeri

Q3

Cilt

37

Sayı

5

Künye

Tozlu, C., Şahin, E., Serencam, H., & Dertli, E. (2019). Production of enantiomerically enriched chiral carbinols using Weissella paramesenteroides as a novel whole cell biocatalyst. Biocatalysis and Biotransformation, 37(5), 388-398.