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

Research output: Contribution to journalArticlepeer-review

34 Citations (Scopus)

Abstract

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.

Original languageEnglish
Pages (from-to)1097-1102
Number of pages6
JournalTetrahedron Asymmetry
Volume9
Issue number7
DOIs
Publication statusPublished - 1998 Apr 9

ASJC Scopus subject areas

  • Catalysis
  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry

Fingerprint Dive into the research topics of 'Rhodococcus rhodochrous IFO 15564-mediated hydrolysis of alicyclic nitriles and amides: Stereoselectivity and use for kinetic resolution and asymmetrization'. Together they form a unique fingerprint.

Cite this