Galactose oxidase models: solution chemistry, and phenoxyl radical generation mediated by the copper status

Chemistry : a European Journal
Fabien MichelJean-Louis Pierre

Abstract

Galactose oxidase (GO) is an enzyme that catalyzes two-electron oxidations. Its active site contains a copper atom coordinated to a tyrosyl radical, the biogenesis of which requires copper and dioxygen. We have recently studied the properties of electrochemically generated mononuclear Cu(II)-phenoxyl radical systems as model compounds of GO. We present here the solution chemistry of these ligands under various copper and dioxygen statuses: N(3)O ligands first chelate Cu(II), leading, in the presence of base, to [Cu(II)(ligand)(CH(3)CN)](+) complexes (ortho-tert-butylated ligands) or [(Cu(II))(2)(ligand)(2)](2+) complexes (ortho-methoxylated ligands). Excess copper(II) then oxidizes the complex to the corresponding mononuclear Cu(II)-phenoxyl radical species. N(2)O(2) tripodal ligands, in the presence of copper(II), afford directly a copper(II)-phenoxyl radical species. Addition of more than two molar equivalents of copper(II) affords a Cu(II)-bis(phenoxyl) diradical species. The donor set of the ligand directs the reaction towards comproportionation for ligands possessing an N(3)O donor set, while disproportionation is observed for ligands possessing an N(2)O(2) donor set. These results are discussed in the light of recent resu...Continue Reading

Citations

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Sep 5, 2015·Inorganic Chemistry·David de BellefeuilleFabrice Thomas
Dec 17, 2005·Dalton Transactions : an International Journal of Inorganic Chemistry·Laurent BenisvyClaire Wilson
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Jun 14, 2006·Journal of Peptide Science : an Official Publication of the European Peptide Society·Mohammed Akhter HossainJean-Louis Pierre
Feb 14, 2007·Dalton Transactions : an International Journal of Inorganic Chemistry·Olaf RotthausJean-Louis Pierre
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Sep 21, 2005·Dalton Transactions : an International Journal of Inorganic Chemistry·Isabelle SylvestreMalcolm A Halcrow
Dec 22, 2005·Chemistry : a European Journal·Olaf RotthausJean-Louis Pierre
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Apr 23, 2011·Inorganic Chemistry·Ross S ForganPeter A Tasker

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