共 33 条
Debaryomyces hansenii as a new biocatalyst in the asymmetric reduction of substituted acetophenones
被引:16
作者:
Sahin, Engin
[1
]
机构:
[1] Bayburt Univ, Dept Food Engn, Fac Engn, TR-69000 Bayburt, Turkey
关键词:
Bio reduction: asymmetric reduction;
whole yeast cells;
Debaryomyces hansenii;
bio transformations;
TRANSFER HYDROGENATION;
KETONES;
HYPERPARATHYROIDISM;
CALCIMIMETICS;
BIOREDUCTION;
CATALYSTS;
ISOLATE;
YEAST;
D O I:
10.1080/10242422.2017.1348500
中图分类号:
Q5 [生物化学];
Q7 [分子生物学];
学科分类号:
071010 ;
081704 ;
摘要:
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 pastirma, 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.
引用
收藏
页码:363 / 371
页数:9
相关论文