Rhodococcus rhodochrous IFO 15564-mediated hydrolysis of alicyclic nitriles and amides:: stereoselectivity and use for kinetic resolution and asymmetrization

被引：37

作者：

Matoishi, K ^{[1
]}

Sano, A ^{[1
]}

Imai, N ^{[1
]}

Yamazaki, T ^{[1
]}

Yokoyama, M ^{[1
]}

Sugai, T ^{[1
]}

Ohta, H ^{[1
]}

机构：

[1] Keio Univ, Dept Chem, Yokohama, Kanagawa 2238522, Japan

来源：

TETRAHEDRON-ASYMMETRY | 1998年 / 9卷 / 07期

关键词：

D O I：

10.1016/S0957-4166(98)00084-6

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

The stereocourse and the selectivity of the hydrolysis of alicyclic mono-and dinitriles and amides mediated by Rhodoroccus rhodochrous IFO 15564 has been examined. The stereochemistry of the substrates, as well as the nature of substituents and presence of double bonds in alicyclic rings greatly affected the rate of hydrolysis by nitrile hydratase and amidase. The rate difference between enantiomers or enantiotopic groups, in some cases, enabled kinetic resolution or asymmetrization. The highest enantioselectivity of amidase was observed in the hydrolysis of 5-benzoyloxy-3-cyclohexene-1-carboxamide (E>200), and both enantiomers of methyl 5-hydroxy-3-cyclohexene-1-carboxylate thus became readily available. (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

页码：1097 / 1102

页数：6

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