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Biological Chemistry

Editor-in-Chief: Brüne, Bernhard

Editorial Board Member: Buchner, Johannes / Lei, Ming / Ludwig, Stephan / Sies, Helmut / Thomas, Douglas D. / Turk, Boris / Wittinghofer, Alfred

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IMPACT FACTOR 2016: 3.273

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1437-4315
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Volume 386, Issue 10 (Oct 2005)

Issues

Combinatorial approaches to functional models for galactose oxidase

Albrecht Berkessel
  • Institut für Organische Chemie der Universität zu Köln, Greinstrasse 4, D-50939 Köln, Germany
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/ Magali Dousset
  • Institut für Organische Chemie der Universität zu Köln, Greinstrasse 4, D-50939 Köln, Germany
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/ Stephan Bulat
  • Institut für Organische Chemie der Universität zu Köln, Greinstrasse 4, D-50939 Köln, Germany
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/ Katja Glaubitz
  • Institut für Organische Chemie der Universität zu Köln, Greinstrasse 4, D-50939 Köln, Germany
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Published Online: 2005-10-12 | DOI: https://doi.org/10.1515/BC.2005.119

Abstract

The copper enzyme galactose oxidase (GOase, EC 1.1.3.9) catalyses the oxidation of D-galactose and other primary alcohols in air to the corresponding aldehydes and hydrogen peroxide. The current mechanistic hypothesis for this two-electron redox reaction involves a Cu(I)/Cu(II) couple and the reversible oxidation of a ligating phenolate (tyrosine residue of the Tyr272-Cys228 conjugate) to a phenoxyl radical. Our approaches to functional models for galactose oxidase comprise both the use of low-molecular-weight copper complexes of a Schiff-base and sulfonamide ligands, and the synthesis/screening of combinatorial libraries. With regard to the latter, we have synthesized (by the IRORI-directed synthesis approach) peptide libraries carrying either His or the redox-active amino acids Tyr, mod-Cys (a model for the Tyr272-Cys228 conjugate) or TOAC (a TEMPO-derived α-amino acid) at four variable positions. After incubation with copper ions, the catalytically active library members were identified by specially designed screening methods.

Keywords: combinatorial chemistry; copper complexes; galactose oxidase; peptide libraries; Schiff-base ligands

About the article

Corresponding author


Received: June 13, 2005

Accepted: July 11, 2005

Published Online: 2005-10-12

Published in Print: 2005-10-01


Citation Information: Biological Chemistry, ISSN (Online) 1437-4315, ISSN (Print) 1431-6730, DOI: https://doi.org/10.1515/BC.2005.119.

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