Characterization of chlorovinylcobalamin, a putative intermediate in reductive degradation of chlorinated ethylenes

Kevin M McCauley; Scott R Wilson; Wilfred A van der Donk

doi:10.1021/ja029692c

Characterization of chlorovinylcobalamin, a putative intermediate in reductive degradation of chlorinated ethylenes

J Am Chem Soc. 2003 Apr 16;125(15):4410-1. doi: 10.1021/ja029692c.

Authors

Kevin M McCauley¹, Scott R Wilson, Wilfred A van der Donk

Affiliation

¹ Department of Chemistry, University of Illinois at Urbana-Champaign, 600 South Mathews Avenue, Urbana, IL 61801, USA.

PMID: 12683797
DOI: 10.1021/ja029692c

Abstract

The first X-ray structure of a vinylcobalamin is reported. Chlorovinylcobalamin is formed in the reaction of cob(I)alamin with chloroacetylene. Subsequently, cob(I)alamin catalyzes the reduction of chlorovinylcobalamin to vinylcobalamin in the presence of excess titanium(III)citrate. Introduction of a chlorine onto the vinyl group of vinylcobalamin greatly changes its reduction potential. These results are discussed with respect to vitamin B12-catalyzed dechlorination of perchloroethylene, a pollutant on the priority list of the EPA.

Publication types

Research Support, Non-U.S. Gov't
Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

Crystallography, X-Ray
Ethylenes / chemistry*
Hydrocarbons, Chlorinated / chemistry*
Oxidation-Reduction
Vinyl Compounds / chemistry*
Vitamin B 12 / analogs & derivatives
Vitamin B 12 / chemical synthesis
Vitamin B 12 / chemistry*

Substances

Ethylenes
Hydrocarbons, Chlorinated
Vinyl Compounds
chlorovinylcobalamin
Vitamin B 12