Aug 25, 1976

Nucleophilic addition reactions of free and enzyme-bound deazaflavin

The Journal of Biological Chemistry
M S Jorns, L B Hersh

Abstract

DeazaFMN-containing glycolate oxidase has been prepared and shown to catalyze the stereospecific transfer of the alpha-hydrogen from substrate to enzyme-bound deazaFMN. The reaction of sulfite, cyanide, and hydroxylamine with several deazaflavin-containing enzymes (glycolate oxidase, D-amino acid oxidase, glucose oxidase, N-methylglutamate synthetase) and free deazaFMN has been examined. All the deazaflavin systems tested form reversible 1:1 complexes with sulfite and cyanide. The pH dependence of the reaction of free deazaFMN with cyanide indicates that cyanide anion is the reacting nucleophile. Hydroxylamine complexes are formed with deazaFMN glycolate oxidase and deazaFAD glucose oxidase. The effectiveness of the various nucleophilic reagents in complex formation decreases in the following order: sulfite greater than cyanide greater than hydroxylamine. The relative stability observed for the sulfite and cyanide complexes formed with various deazaflavin systems (glycolate oxidase greater than D-amino acid oxidase greater than free deazaFMN) follows the same trend observed for the stability of the sulfite complexes formed with the corresponding flavin system. A correlation is also observed between the reduction potential (E'o)...Continue Reading

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Mentioned in this Paper

(S)-2-Hydroxy-acid oxidase
D-Amino Acid Dehydrogenase
HAO2 gene
Covalent Interaction
Alcohol Oxidoreductases
Enzymes, antithrombotic
DAO gene
Complex (molecular entity)
Oxidase
5-deaza-FMN

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