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

Kaori Matoishi, Akio Sano, Nori Imai, Takahiro Yamazaki, Masahiro Yokoyama, Takeshi Sugai, Hiromichi Ohta

研究成果: Article査読

36 被引用数 (Scopus)

抄録

The stereocourse and the selectivity of the hydrolysis of alicyclic mono- and dinitriles and amides mediated by Rhodococcus 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.

本文言語English
ページ(範囲)1097-1102
ページ数6
ジャーナルTetrahedron Asymmetry
9
7
DOI
出版ステータスPublished - 1998 4 9

ASJC Scopus subject areas

  • 触媒
  • 物理化学および理論化学
  • 有機化学
  • 無機化学

フィンガープリント

「Rhodococcus rhodochrous IFO 15564-mediated hydrolysis of alicyclic nitriles and amides: Stereoselectivity and use for kinetic resolution and asymmetrization」の研究トピックを掘り下げます。これらがまとまってユニークなフィンガープリントを構成します。

引用スタイル