Nitrile biotransformations for highly enantioselective synthesis of oxiranecarboxamides with tertiary and quaternary stereocenters; Efficient chemoenzymatic approaches to enantiopure alpha-methylated serine and isoserine derivatives

doi:10.1021/jo0482515

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	Nitrile biotransformations for highly enantioselective synthesis of oxiranecarboxamides with tertiary and quaternary stereocenters; Efficient chemoenzymatic approaches to enantiopure alpha-methylated serine and isoserine derivatives
	Wang, MX; Deng, G; Wang, DX; Zheng, QY
刊名	JOURNAL OF ORGANIC CHEMISTRY
	2005-04-01
卷号	70 期号:7 页码:2439-2444
ISSN号	0022-3263
DOI	10.1021/jo0482515
英文摘要	Biotransformations of a number of differently substituted and configured oxiranecarbonitriles using Rhodococcus sp. AJ270, a microbial whole-cell catalyst that contains nitrile hydratase/amidase, were studied. While almost all trans-configured 3-aryl-2-methyloxiranecarbonitriles and 2,3-dimethyl-3-phenyloxiranecarbonitrile were efficiently hydrated by the action of the less enantioselective nitrile hydratase, the amidase exhibited excellent 2S,3R-enantioselectivity against 2-methyl-3-(para-substituted-phenyl)oxiranecarboxamides. Under very mild conditions, biotrans-formations of nitriles provided an efficient and practical synthesis of 2R,3S-(-)-3-aryl-2-methyloxiranecarboxamides, electrophilic epoxides with tertiary and quaternary stereocenters, in excellent yield with enantiomeric excess greater than 99.5%. The synthetic applications of the resulting enantiomerically pure epoxides were demonstrated by convenient and straightforward syntheses of polyfunctionalized chiral molecules possessing a quaternary stereocenter such as R-(+)-2-hydroxy2-methyl-3-phenylpropionic acid, 2R,3R-(-)-3-amino-2-hydroxy-2-methyl-3-phenylpropionic acid, and 2S,3S-(+)-2-amino-3-hydroxy-2-methyl-3-phenylpropionic acid, employing the regio- and stereospecific epoxide ring opening reactions of 2R,3S-(-)-2-methyl-3-phenyloxiranecarboxamide as the key steps.
语种	英语
出版者	AMER CHEMICAL SOC
WOS记录号	WOS:000227928200003
内容类型	期刊论文
源URL	[http://ir.iccas.ac.cn/handle/121111/56397]
专题	中国科学院化学研究所
通讯作者	Wang, MX
作者单位	Chinese Acad Sci, Inst Chem, Ctr Mol Sci, Lab Chem Biol, Beijing 100080, Peoples R China
推荐引用方式 GB/T 7714	Wang, MX,Deng, G,Wang, DX,et al. Nitrile biotransformations for highly enantioselective synthesis of oxiranecarboxamides with tertiary and quaternary stereocenters; Efficient chemoenzymatic approaches to enantiopure alpha-methylated serine and isoserine derivatives[J]. JOURNAL OF ORGANIC CHEMISTRY,2005,70(7):2439-2444.
APA	Wang, MX,Deng, G,Wang, DX,&Zheng, QY.(2005).Nitrile biotransformations for highly enantioselective synthesis of oxiranecarboxamides with tertiary and quaternary stereocenters; Efficient chemoenzymatic approaches to enantiopure alpha-methylated serine and isoserine derivatives.JOURNAL OF ORGANIC CHEMISTRY,70(7),2439-2444.
MLA	Wang, MX,et al."Nitrile biotransformations for highly enantioselective synthesis of oxiranecarboxamides with tertiary and quaternary stereocenters; Efficient chemoenzymatic approaches to enantiopure alpha-methylated serine and isoserine derivatives".JOURNAL OF ORGANIC CHEMISTRY 70.7(2005):2439-2444.