Debaryomyces hansenii as a new biocatalyst in the asymmetric reduction of substituted acetophenones
Küçük Resim Yok
Tarih
2017
Yazarlar
Dergi Başlığı
Dergi ISSN
Cilt Başlığı
Yayıncı
Taylor and Francis Ltd
Erişim Hakkı
info:eu-repo/semantics/closedAccess
Özet
Chiral secondary alcohols are convenient mediator for the synthesis of biologically active compounds and natural products. In this study fifteen yeast strains belonging to three food originated yeast species Debaryomyces hansenii, Saccharomyces cerevisiae and Hanseniaspora guilliermondii were tested for their capability for the asymmetric reduction of acetophenone to 1-phenylethanol as biocatalyst microorganisms. Of these strains, Debaryomyces hansenii P1 strain showed an effective asymmetric reduction ability. Under optimized conditions, substituted acetophenones were converted to the corresponding optically active secondary alcohols in up to 99% enantiomeric excess and at high conversion rates. This is the first report on the enantioselective reduction of acetophenone by D. hansenii P1 from pastırma, a fermented Turkish meat product. The preparative scale asymmetric bio reduction of 3-methoxy acetophenone 1g by D. hansenii P1 gave (R)-1-(3-methoxyphenyl) ethanol 2g 82% yield, and >99% enantiomeric excess. Compound 2g can be used for the synthesis of (+)-NPS-R-568 [3-(2-chlorophenyl)-N-[(1R)-1-(3-methoxyphenly) ethyl] propan-1-amine] which have a great potential for the treatment of primary and secondary hyper-parathyroidism. In addition, D. hansenii P1 successfully reduced acetophenone derivatives. This study showed that this yeast can be used industrially to produce enantiomerically pure chiral secondary alcohols, which can be easily converted to different functional groups. © 2017 Informa UK Limited, trading as Taylor & Francis Group.
Açıklama
Anahtar Kelimeler
Bio reduction: asymmetric reduction, bio transformations, Debaryomyces hansenii, whole yeast cells, Amorphous alloys, Bioactivity, Biocatalysts, Condensation reactions, Enantiomers, Ethanol, Yeast, Asymmetric reduction, Biologically active compounds, Chiral secondary alcohols, Debaryomyces hansenii, Enantiomeric excess, Enantioselective reduction, Optimized conditions, Yeast cell, Ketones, 1 (2 bromophenyl)ethanol, 1 (2 chlorophenyl)ethanol, 1 (2 methoxyphenyl)ethanol, 1 (2 nitrophenyl)ethanol, 1 (3 chlorophenyl)ethanol, 1 (3 methoxyphenyl)ethanol, 1 (4 biphenyl)ethanol, 1 (4 bromophenyl)ethanol, 1 (4 chlorophenyl)ethanol, 1 (4 methoxyphenyl)ethanol, 1 (4 nitrophenyl)ethanol, 1 (4 tolyl)ethanol, 1 phenylethanol, acetophenone derivative, alcohol derivative, ketone derivative, natural product, unclassified drug, Article, asymmetric synthesis, biocatalyst, carbon nuclear magnetic resonance, chirality, Debaryomyces hansenii, drug synthesis, enantiomer, enantioselectivity, fermentation, flow rate, fungal cell culture, fungal strain, fungus isolation, Hanseniaspora guilliermondii, high performance liquid chromatography, nonhuman, primary hyperparathyroidism, process optimization, proton nuclear magnetic resonance, reduction (chemistry), retention time, Saccharomyces cerevisiae, secondary hyperparathyroidism, Bio reduction: asymmetric reduction, bio transformations, Debaryomyces hansenii, whole yeast cells, Amorphous alloys, Bioactivity, Biocatalysts, Condensation reactions, Enantiomers, Ethanol, Yeast, Asymmetric reduction, Biologically active compounds, Chiral secondary alcohols, Debaryomyces hansenii, Enantiomeric excess, Enantioselective reduction, Optimized conditions, Yeast cell, Ketones, 1 (2 bromophenyl)ethanol, 1 (2 chlorophenyl)ethanol, 1 (2 methoxyphenyl)ethanol, 1 (2 nitrophenyl)ethanol, 1 (3 chlorophenyl)ethanol, 1 (3 methoxyphenyl)ethanol, 1 (4 biphenyl)ethanol, 1 (4 bromophenyl)ethanol, 1 (4 chlorophenyl)ethanol, 1 (4 methoxyphenyl)ethanol, 1 (4 nitrophenyl)ethanol, 1 (4 tolyl)ethanol, 1 phenylethanol, acetophenone derivative, alcohol derivative, ketone derivative, natural product, unclassified drug, Article, asymmetric synthesis, biocatalyst, carbon nuclear magnetic resonance, chirality, Debaryomyces hansenii, drug synthesis, enantiomer, enantioselectivity, fermentation, flow rate, fungal cell culture, fungal strain, fungus isolation, Hanseniaspora guilliermondii, high performance liquid chromatography, nonhuman, primary hyperparathyroidism, process optimization, proton nuclear magnetic resonance, reduction (chemistry), retention time, Saccharomyces cerevisiae, secondary hyperparathyroidism
Kaynak
Biocatalysis and Biotransformation
WoS Q Değeri
Q4
Scopus Q Değeri
Q3
Cilt
35
Sayı
5
