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 journalArticle

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

Fingerprint

amidase
Rhodococcus
Stereoselectivity
Nitriles
nitriles
Amides
amides
hydrolysis
Hydrolysis
Enantiomers
enantiomers
Kinetics
kinetics
Stereochemistry
Enantioselectivity
stereochemistry
carboxylates
selectivity
rings
Substrates

ASJC Scopus subject areas

  • Inorganic Chemistry
  • Organic Chemistry
  • Materials Chemistry
  • Drug Discovery

Cite this

Rhodococcus rhodochrous IFO 15564-mediated hydrolysis of alicyclic nitriles and amides : Stereoselectivity and use for kinetic resolution and asymmetrization. / Matoishi, Kaori; Sano, Akio; Imai, Nori; Yamazaki, Takahiro; Yokoyama, Masahiro; Sugai, Takeshi; Ohta, Hiromichi.

In: Tetrahedron Asymmetry, Vol. 9, No. 7, 09.04.1998, p. 1097-1102.

Research output: Contribution to journalArticle

Matoishi, Kaori ; Sano, Akio ; Imai, Nori ; Yamazaki, Takahiro ; Yokoyama, Masahiro ; Sugai, Takeshi ; Ohta, Hiromichi. / Rhodococcus rhodochrous IFO 15564-mediated hydrolysis of alicyclic nitriles and amides : Stereoselectivity and use for kinetic resolution and asymmetrization. In: Tetrahedron Asymmetry. 1998 ; Vol. 9, No. 7. pp. 1097-1102.
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