PMID: 18348Jun 1, 1977

On the structure of flavin-oxygen intermediates involved in enzymatic reactions

European Journal of Biochemistry
S GhislaM Husein

Abstract

During the catalytic reactions of flavoprotein hydroxylases and bacterial luciferase, flavin peroxides are formed as intermediates [see Massey, V. and Hemmerich, P. (1976) in The Enzymes, 3rd edn (P. Boyer, ed.) pp. 421--505, Academic Press, New York]. These intermediates have been postulated to be C(4a) derivatives of the flavin coenzyme. To test this hypothesis, modified flavin coenzymes carrying an oxygen substituent at position C(4a) of the isoalloxazine ring were synthesized. They are tightly bound by the apoenzymes of D-amino acid oxidase, p-hydroxybenzoate hydroxylase and lactate oxidase; the resulting complexes show spectral properties closely similar to those of the transient oxygen adducts of the hydroxylases. The optical spectra of the lumiflavin model compounds were found to be highly dependent on the solvent environment and nature of the subsituents. Under appropriate conditions they simulate satisfactorily the spectra of the transient enzymatic oxygen adducts. The results support the proposal that the primary oxygen adducts formed with these flavoproteins on reaction of the reduced enzymes with oxygen are flavin C(4a) peroxides.

References

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Citations

Jan 1, 1989·The International Journal of Biochemistry·V LeskovacM Radulović
Jan 1, 1989·The International Journal of Biochemistry·V LeskovacM Radulović
Jun 1, 1982·Applied and Environmental Microbiology·W R MahaffeyA W Bourquin
Oct 31, 2001·European Journal of Biochemistry·P ChaiyenP Wilairat
Dec 1, 1978·Proceedings of the National Academy of Sciences of the United States of America·S GhislaJ M Lhoste
May 1, 1984·Proceedings of the National Academy of Sciences of the United States of America·M KurfürstJ W Hastings
Aug 15, 1977·European Journal of Biochemistry·V Favaudon
Apr 1, 1982·European Journal of Biochemistry·M KurfürstJ W Hastings
Oct 26, 2013·FEBS Letters·Dirk TischlerGeorge T Gassner
Apr 9, 2009·Bioelectrochemistry·Soren Demin, Elizabeth A H Hall
Oct 18, 2016·Photochemistry and Photobiology·John Lee
May 15, 1985·Archives of Biochemistry and Biophysics·C Gomez-Moreno, D E Edmondson
Nov 30, 2018·Photochemistry and Photobiology·John LeeAntonie J W G Visser
Sep 15, 2010·Photochemical & Photobiological Sciences : Official Journal of the European Photochemistry Association and the European Society for Photobiology·Robert LechnerBurkhard König
Jan 1, 1989·Critical Reviews in Biotechnology·F S Sariaslani
Jun 1, 1995·European Journal of Biochemistry·B Langkau, S Ghisla
Jul 22, 2014·Angewandte Chemie·Samer GozemMassimo Olivucci

Related Concepts

Apoenzymes
D-Amino Acid Dehydrogenase
Flavins
Mixed Function Oxygenases
Luciferases
Oxidation-Reduction
Oxidase
Peroxides
Plasma Protein Binding Capacity
4-Hydroxybenzoate 3-monooxygenase

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