Nitrile biotransformations for the synthesis of enantiomerically enriched beta(2)-, and beta(3)-hydroxy and -alkoxy acids and amides, a dramatic O-substituent effect of the substrates on enantioselectivity

doi:10.1016/j.tetasy.2008.01.017

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	Nitrile biotransformations for the synthesis of enantiomerically enriched beta(2)-, and beta(3)-hydroxy and -alkoxy acids and amides, a dramatic O-substituent effect of the substrates on enantioselectivity
	Ma, Da-You; Wang, De-Xian; Pan, Jie; Huang, Zhi-Tang; Wang, Mei-Xiang
刊名	TETRAHEDRON-ASYMMETRY
	2008-02-19
卷号	19 期号:3 页码:322-329
ISSN号	0957-4166
DOI	10.1016/j.tetasy.2008.01.017
英文摘要	Rhodococcus erythropolis AJ270, a nitrile hydratase/amidase-containing microbial whole cell catalyst, is able to catalyze the hydrolysis of a number of P-hydroxy and beta-alkoxy nitriles under very mild conditions. Both the efficiency and enantio selectivity of the biocatalysis. however, were strongly dependent upon the structures of both nitrile and amide substrates. When biotransformations of racemic 3-hydroxy-3-phenylpropionitrile and 2-hydroxymethyl-3-phenylpropionitrile gave low enantioselectivity, their O-methylated isomers underwent highly efficient and enantio selective biocatalytic reactions to afford highly enantioenriched beta(2)- and beta(3)-hydroxy amide and acid derivatives in excellent yield. The study has provided an example of simple and very convenient substrate engineering method to increase the enantioselectivity of the biocatalytic reaction. (C) 2008 Elsevier Ltd. All rights reserved.
语种	英语
出版者	PERGAMON-ELSEVIER SCIENCE LTD
WOS记录号	WOS:000254160800010
内容类型	期刊论文
源URL	[http://ir.iccas.ac.cn/handle/121111/64133]
专题	中国科学院化学研究所
通讯作者	Wang, Mei-Xiang
作者单位	Chinese Acad Sci, Inst Chem, Biol Chem Lab, Beijing Natl Lab Mol Sci, Beijing 100080, Peoples R China
推荐引用方式 GB/T 7714	Ma, Da-You,Wang, De-Xian,Pan, Jie,et al. Nitrile biotransformations for the synthesis of enantiomerically enriched beta(2)-, and beta(3)-hydroxy and -alkoxy acids and amides, a dramatic O-substituent effect of the substrates on enantioselectivity[J]. TETRAHEDRON-ASYMMETRY,2008,19(3):322-329.
APA	Ma, Da-You,Wang, De-Xian,Pan, Jie,Huang, Zhi-Tang,&Wang, Mei-Xiang.(2008).Nitrile biotransformations for the synthesis of enantiomerically enriched beta(2)-, and beta(3)-hydroxy and -alkoxy acids and amides, a dramatic O-substituent effect of the substrates on enantioselectivity.TETRAHEDRON-ASYMMETRY,19(3),322-329.
MLA	Ma, Da-You,et al."Nitrile biotransformations for the synthesis of enantiomerically enriched beta(2)-, and beta(3)-hydroxy and -alkoxy acids and amides, a dramatic O-substituent effect of the substrates on enantioselectivity".TETRAHEDRON-ASYMMETRY 19.3(2008):322-329.