Methane monooxygenase biotransformations

Highly stereoselective hydroxylation of 3-methylcyclohexene by methane monooxygenase: Steric and electronic effects on product distribution

David J. Leak, Stephen L.R. Ellison, Christopher Murricane, Peter B. Baker

Research output: Contribution to journalArticle

Abstract

Cell extracts containing soluble methane monooxygenase from Methylococcus capsulatus, Methylosinus sporium and Methylosinus trichosporium converted 3-methylcyclohexene to predominantly cis-4-methylcyclohex-2-enol, contrary to an earlier suggestion of rearrangement products. In the case of M. capsulatus extracts, this comprised 90% of the total products. The product mixture was consistent with predictions based on chemical reactivity of the substrate, steric effects in the substrate and products and enzymic constraints operating in concert.

Original languageEnglish
Pages (from-to)197-204
Number of pages8
JournalBiocatalysis and Biotransformation
Volume1
Issue number3
DOIs
Publication statusPublished - 1 Jan 1988

Keywords

  • Hydroxylation stereospecificity
  • Methylococcus capsulatus
  • Methylosinus sporium
  • Methylosinus trichosporium
  • Monooxygenase

ASJC Scopus subject areas

  • Biotechnology
  • Catalysis
  • Biochemistry

Cite this

Methane monooxygenase biotransformations : Highly stereoselective hydroxylation of 3-methylcyclohexene by methane monooxygenase: Steric and electronic effects on product distribution. / Leak, David J.; Ellison, Stephen L.R.; Murricane, Christopher; Baker, Peter B.

In: Biocatalysis and Biotransformation, Vol. 1, No. 3, 01.01.1988, p. 197-204.

Research output: Contribution to journalArticle

@article{13182a68817c48e5baa75499ffdaf8bd,
title = "Methane monooxygenase biotransformations: Highly stereoselective hydroxylation of 3-methylcyclohexene by methane monooxygenase: Steric and electronic effects on product distribution",
abstract = "Cell extracts containing soluble methane monooxygenase from Methylococcus capsulatus, Methylosinus sporium and Methylosinus trichosporium converted 3-methylcyclohexene to predominantly cis-4-methylcyclohex-2-enol, contrary to an earlier suggestion of rearrangement products. In the case of M. capsulatus extracts, this comprised 90{\%} of the total products. The product mixture was consistent with predictions based on chemical reactivity of the substrate, steric effects in the substrate and products and enzymic constraints operating in concert.",
keywords = "Hydroxylation stereospecificity, Methylococcus capsulatus, Methylosinus sporium, Methylosinus trichosporium, Monooxygenase",
author = "Leak, {David J.} and Ellison, {Stephen L.R.} and Christopher Murricane and Baker, {Peter B.}",
year = "1988",
month = "1",
day = "1",
doi = "10.3109/10242428809014846",
language = "English",
volume = "1",
pages = "197--204",
journal = "Biocatalysis and Biotransformation",
issn = "1024-2422",
publisher = "Informa Healthcare",
number = "3",

}

TY - JOUR

T1 - Methane monooxygenase biotransformations

T2 - Highly stereoselective hydroxylation of 3-methylcyclohexene by methane monooxygenase: Steric and electronic effects on product distribution

AU - Leak, David J.

AU - Ellison, Stephen L.R.

AU - Murricane, Christopher

AU - Baker, Peter B.

PY - 1988/1/1

Y1 - 1988/1/1

N2 - Cell extracts containing soluble methane monooxygenase from Methylococcus capsulatus, Methylosinus sporium and Methylosinus trichosporium converted 3-methylcyclohexene to predominantly cis-4-methylcyclohex-2-enol, contrary to an earlier suggestion of rearrangement products. In the case of M. capsulatus extracts, this comprised 90% of the total products. The product mixture was consistent with predictions based on chemical reactivity of the substrate, steric effects in the substrate and products and enzymic constraints operating in concert.

AB - Cell extracts containing soluble methane monooxygenase from Methylococcus capsulatus, Methylosinus sporium and Methylosinus trichosporium converted 3-methylcyclohexene to predominantly cis-4-methylcyclohex-2-enol, contrary to an earlier suggestion of rearrangement products. In the case of M. capsulatus extracts, this comprised 90% of the total products. The product mixture was consistent with predictions based on chemical reactivity of the substrate, steric effects in the substrate and products and enzymic constraints operating in concert.

KW - Hydroxylation stereospecificity

KW - Methylococcus capsulatus

KW - Methylosinus sporium

KW - Methylosinus trichosporium

KW - Monooxygenase

UR - http://www.scopus.com/inward/record.url?scp=84907036634&partnerID=8YFLogxK

U2 - 10.3109/10242428809014846

DO - 10.3109/10242428809014846

M3 - Article

VL - 1

SP - 197

EP - 204

JO - Biocatalysis and Biotransformation

JF - Biocatalysis and Biotransformation

SN - 1024-2422

IS - 3

ER -