Literature DB >> 6587349

Epoxidation of olefins by cytochrome P-450 model compounds: mechanism of oxygen atom transfer.

J P Collman, J I Brauman, B Meunier, S A Raybuck, T Kodadek.   

Abstract

The mechanism of the Mn(III) porphyrin-catalyzed epoxidation of olefins by lithium hypochlorite is examined. The active oxidant is thought to be a high-valent manganese-oxo complex. It is shown that a relatively stable intermediate is reversibly formed upon interaction of the olefin and the oxo complex. The decomposition of this intermediate to Mn(III) porphyrin and epoxide is the rate-determining step of the catalytic cycle. Some analogies to the biochemical epoxidation of olefins catalyzed by cytochrome P-450 are discussed.

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Year:  1984        PMID： 6587349      PMCID： PMC345259          DOI： 10.1073/pnas.81.10.3245

Source DB:  PubMed          Journal:  Proc Natl Acad Sci U S A        ISSN： 0027-8424            Impact factor:   11.205


  9 in total

1.  Loss of haem in rat liver caused by the porphyrogenic agent 2-allyl-2-isopropylacetamide.

Authors:  F De Matteis
Journal:  Biochem J       Date:  1971-10       Impact factor: 3.857

2.  Destruction of cytochrome P-450 by 2-isopropyl-4-pentenamide and methyl 2-isopropyl-4-pentenoate: mass spectrometric characterization of prosthetic heme adducts and nonparticipation of epoxide metabolites.

Authors:  P R Ortiz de Montellano; G S Yost; B A Mico; S E Dinizo; M A Correia; H Kumbara
Journal:  Arch Biochem Biophys       Date:  1979-10-15       Impact factor: 4.013

Review 3.  Oxygen activation by cytochrome P-450.

Authors:  R E White; M J Coon
Journal:  Annu Rev Biochem       Date:  1980       Impact factor: 23.643

4.  Destruction of cytochrome P-450 by ethylene and other olefins.

Authors:  P R Ortiz de Montellano; B A Mico
Journal:  Mol Pharmacol       Date:  1980-07       Impact factor: 4.436

5.  Self-catalyzed inactivation of hepatic cytochrome P-450 by ethynyl substrates.

Authors:  P R Ortiz de Montellano; K L Kunze
Journal:  J Biol Chem       Date:  1980-06-25       Impact factor: 5.157

6.  Oxygenation of hydrocarbons by cytochrome P-450 model compounds: modification of reactivity by axial ligands.

Authors:  J P Collman; T Kodadek; S A Raybuck; B Meunier
Journal:  Proc Natl Acad Sci U S A       Date:  1983-11       Impact factor: 11.205

7.  Self-catalyzed destruction of cytochrome P-450: covalent binding of ethynyl sterols to prosthetic heme.

Authors:  P R Ortiz de Montellano; K L Kunze; G S Yost; B A Mico
Journal:  Proc Natl Acad Sci U S A       Date:  1979-02       Impact factor: 11.205

8.  Destruction of cytochrome P-450 by vinyl fluoride, fluroxene, and acetylene. Evidence for a radical intermediate in olefin oxidation.

Authors:  P R Ortiz de Montellano; K L Kunze; H S Beilan; C Wheeler
Journal:  Biochemistry       Date:  1982-03-16       Impact factor: 3.162

9.  Determination of partition ratios for allylisopropylacetamide during suicidal processing by a phenobarbital-induced cytochrome P-450 isozyme from rat liver.

Authors:  M J Loosemore; G N Wogan; C Walsh
Journal:  J Biol Chem       Date:  1981-08-25       Impact factor: 5.157
  9 in total
  4 in total

1.  Observations and comments on the mechanism of epoxidation of alkenes by manganese(III) porphyrins with hypochlorite.

Authors:  R W Lee; P C Nakagaki; P N Balasubramanian; T C Bruice
Journal:  Proc Natl Acad Sci U S A       Date:  1988-02       Impact factor: 11.205

2.  Ethylene metabolism in Pisum sativum L.

Authors:  I O Sanders; A R Smith; M A Hall
Journal:  Planta       Date:  1989-08       Impact factor: 4.116

3.  Experimental and theoretical studies of the porphyrin ligand effect on the electronic structure and reactivity of oxoiron(iv) porphyrin π-cation-radical complexes.

Authors:  Yuri Ishimizu; Zhifeng Ma; Masahiko Hada; Hiroshi Fujii
Journal:  J Biol Inorg Chem       Date:  2019-05-21       Impact factor: 3.358

4.  Pseudotetrahedral manganese complexes supported by the anionic tris(phosphino)borate ligand [PhBP(iPr)3].

Authors:  Connie C Lu; Jonas C Peters
Journal:  Inorg Chem       Date:  2006-10-16       Impact factor: 5.165
  4 in total

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