A bis(η5-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

France-Aimée  Alphonse; Rehana Karim; Céline  Cano-Soumillac; Marielle Hebray; David Collison; David Garner; John Joule

doi:10.1016/j.tet.2005.08.095

A bis(η5-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

France-Aimée Alphonse, Rehana Karim, Céline Cano-Soumillac, Marielle Hebray, David Collison, David Garner, John Joule

Research output: Contribution to journal › Article › peer-review

Abstract

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 (η5-C5H5)Co complex.

Original language	English
Pages (from-to)	11010-11019
Number of pages	10
Journal	Tetrahedron Letters
Volume	61
Issue number	46
DOIs	https://doi.org/10.1016/j.tet.2005.08.095
Publication status	Published - 2005

Keywords

Aldehyde
Tungsten
Ligand
DMSO reductase family
Pyrano[2,3-b]quinoxaline
Enedithiolate

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Alphonse, F-A., Karim, R., Cano-Soumillac, C., Hebray, M., Collison, D., Garner, D., & Joule, J. (2005). A bis(η5-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. Tetrahedron Letters, 61(46), 11010-11019. https://doi.org/10.1016/j.tet.2005.08.095

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title = "A bis(η5-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",

abstract = "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 (η5-C5H5)Co complex.",

keywords = "Aldehyde, Tungsten, Ligand, DMSO reductase family, Pyrano[2,3-b]quinoxaline, Enedithiolate",

author = "France-Aim{\'e}e Alphonse and Rehana Karim and C{\'e}line Cano-Soumillac and Marielle Hebray and David Collison and David Garner and John Joule",

year = "2005",

doi = "10.1016/j.tet.2005.08.095",

language = "English",

volume = "61",

pages = "11010--11019",

journal = "Tetrahedron Letters",

issn = "0040-4039",

publisher = "Elsevier",

number = "46",

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Alphonse, F-A, Karim, R, Cano-Soumillac, C, Hebray, M, Collison, D, Garner, D & Joule, J 2005, 'A bis(η5-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', Tetrahedron Letters, vol. 61, no. 46, pp. 11010-11019. https://doi.org/10.1016/j.tet.2005.08.095

A bis(η5-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. / Alphonse, France-Aimée ; Karim, Rehana; Cano-Soumillac, Céline et al.

In: Tetrahedron Letters, Vol. 61, No. 46, 2005, p. 11010-11019.

Research output: Contribution to journal › Article › peer-review

TY - JOUR

T1 - A bis(η5-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

AU - Alphonse, France-Aimée

AU - Karim, Rehana

AU - Cano-Soumillac, Céline

AU - Hebray, Marielle

AU - Collison, David

AU - Garner, David

AU - Joule, John

PY - 2005

Y1 - 2005

N2 - 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 (η5-C5H5)Co complex.

AB - 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 (η5-C5H5)Co complex.

KW - Aldehyde

KW - Tungsten

KW - Ligand

KW - DMSO reductase family

KW - Pyrano[2,3-b]quinoxaline

KW - Enedithiolate

U2 - 10.1016/j.tet.2005.08.095

DO - 10.1016/j.tet.2005.08.095

M3 - Article

VL - 61

SP - 11010

EP - 11019

JO - Tetrahedron Letters

JF - Tetrahedron Letters

SN - 0040-4039

IS - 46

ER -

Alphonse F-A, Karim R, Cano-Soumillac C, Hebray M, Collison D, Garner D et al. A bis(η5-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. Tetrahedron Letters. 2005;61(46):11010-11019. doi: 10.1016/j.tet.2005.08.095