Literature DB >> 2271658

Enantioselective oxidations of sulfides catalyzed by chloroperoxidase.

S Colonna1, N Gaggero, A Manfredi, L Casella, M Gullotti, G Carrea, P Pasta.   

Abstract

The chloroperoxidase-catalyzed and horseradish peroxidase catalyzed oxidations of sulfides by tert-butyl and other peroxides have been investigated. The former metal enzyme afforded the corresponding sulfoxides having R absolute configuration in up to 92% enantiomeric excess (ee), whereas the latter gave racemic products. The various factors that control the enantioselectivity of the oxygenation have been examined.

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Year:  1990        PMID: 2271658     DOI: 10.1021/bi00498a006

Source DB:  PubMed          Journal:  Biochemistry        ISSN: 0006-2960            Impact factor:   3.162


  12 in total

1.  Opposite enantioselectivities of two phenotypically and genotypically similar strains of Pseudomonas frederiksbergensis in bacterial whole-cell sulfoxidation.

Authors:  Waldemar Adam; Frank Heckel; Chantu R Saha-Möller; Marcus Taupp; Jean-Marie Meyer; Peter Schreier
Journal:  Appl Environ Microbiol       Date:  2005-04       Impact factor: 4.792

2.  Mössbauer and electron paramagnetic resonance studies of chloroperoxidase following mechanism-based inactivation with allylbenzene.

Authors:  P G Debrunner; A F Dexter; C E Schulz; Y M Xia; L P Hager
Journal:  Proc Natl Acad Sci U S A       Date:  1996-11-12       Impact factor: 11.205

3.  Replacement of the proximal heme thiolate ligand in chloroperoxidase with a histidine residue.

Authors:  X Yi; M Mroczko; K M Manoj; X Wang; L P Hager
Journal:  Proc Natl Acad Sci U S A       Date:  1999-10-26       Impact factor: 11.205

4.  Cloning and Characterization of a Novel Esterase from Rhodococcus sp. for Highly Enantioselective Synthesis of a Chiral Cilastatin Precursor.

Authors:  Yan Zhang; Jiang Pan; Zheng-Jiao Luan; Guo-Chao Xu; Sunghoon Park; Jian-He Xu
Journal:  Appl Environ Microbiol       Date:  2014-09-19       Impact factor: 4.792

5.  Enantiospecificity of chloroperoxidase-catalyzed epoxidation: biased molecular dynamics study of a cis-β-methylstyrene/chloroperoxidase-compound I complex.

Authors:  Alexander N Morozov; Cassian D'Cunha; Carlos A Alvarez; David C Chatfield
Journal:  Biophys J       Date:  2011-02-16       Impact factor: 4.033

6.  Sulphoxidation reaction catalysed by myeloperoxidase from human leucocytes.

Authors:  C Capeillère-Blandin; C Martin; N Gaggero; P Pasta; G Carrea; S Colonna
Journal:  Biochem J       Date:  1998-10-01       Impact factor: 3.857

7.  Paramagnetic nuclear magnetic resonance relaxation and molecular mechanics studies of the chloroperoxidase-indole complex: insights into the mechanism of chloroperoxidase-catalyzed regioselective oxidation of indole.

Authors:  Rui Zhang; Qinghao He; David Chatfield; Xiaotang Wang
Journal:  Biochemistry       Date:  2013-05-14       Impact factor: 3.162

Review 8.  Synthetic Fe/Cu Complexes: Toward Understanding Heme-Copper Oxidase Structure and Function.

Authors:  Suzanne M Adam; Gayan B Wijeratne; Patrick J Rogler; Daniel E Diaz; David A Quist; Jeffrey J Liu; Kenneth D Karlin
Journal:  Chem Rev       Date:  2018-10-29       Impact factor: 60.622

9.  The coprophilous mushroom Coprinus radians secretes a haloperoxidase that catalyzes aromatic peroxygenation.

Authors:  Dau Hung Anh; René Ullrich; Dirk Benndorf; Ales Svatos; Alexander Muck; Martin Hofrichter
Journal:  Appl Environ Microbiol       Date:  2007-06-29       Impact factor: 4.792

10.  Oxidation of thioanisole and p-methoxythioanisole by lignin peroxidase: kinetic evidence of a direct reaction between compound II and a radical cation.

Authors:  Thomas B Brück; Maria Francesca Gerini; Enrico Baciocchi; Patricia J Harvey
Journal:  Biochem J       Date:  2003-09-15       Impact factor: 3.857

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