A bis(eta(5)-cyclopentadienyl)cobalt complex of a bis-dithiolene: a chemical analogue of the metal centres of the DMSO reductase family of molybdenum and tungsten enzymes, in particular ferredoxin aldehyde oxidoreductase

The synthesis is described of a bis-ene-1,2-dithiolate pro-ligand, designed to model the stereochemical situation in the cofactor of the tungsten enzyme ferredoxin aldehyde oxidoreductase from Pyrococcus furiosus. Each masked ene-1,2-dithiolate unit is mounted on a pyrano[2,3-b]tetrahydroquinoxaline...

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Bibliographic Details
Published inTetrahedron Vol. 61; no. 46; pp. 11010 - 11019
Main Authors Alphonse, FA, Karim, R, Cano-Soumillac, C, Hebray, M, Collison, D, Garner, CD, Joule, JA
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier 14.11.2005
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
CRYSTAL-STRUCTURE
aldehyde
MODEL
ligand
enedithiolate
FORMS
DMSO reductase family
tungsten
ELECTRON-TRANSFER
OXIDASE
pyrano[2,3-b]quinoxaline
COFACTOR
COBALT
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Summary:The synthesis is described of a bis-ene-1,2-dithiolate pro-ligand, designed to model the stereochemical situation in the cofactor of the tungsten enzyme ferredoxin aldehyde oxidoreductase from Pyrococcus furiosus. Each masked ene-1,2-dithiolate unit is mounted on a pyrano[2,3-b]tetrahydroquinoxaline tricycle, comparable to the pyrano[2,3-g]tetrahydropteridines found in all molybdoenzymes and tungsten analogues. Hydrolytic release of the bis-ligand was confirmed by its entrapment as a double (eta(5)-C5H5)CO complex. (c) 2005 Elsevier Ltd. All rights reserved.
ISSN:0040-4020
DOI:10.1016/j.tet.2005.08.095