Reaction of enzyme-bound 5-deazaflavin with peroxides. Pyrimidine ring contraction via an epoxide intermediate.

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Reaction of enzyme-bound 5-deazaflavin with peroxides. Pyrimidine ring contraction via an epoxide intermediate.

Reaction of peroxides with 5-deazaflavin bound to glucose oxidase, lactate oxidase, or D-amino acid oxidase results in the formation of 5-deazaflavin 4a, 5-epoxide. The reaction of D-amino acid oxidase with m-chloroperoxybenzoate is an exception since the reagent reacts rapidly with the protein moiety to form m-chlorobenzoate which then binds noncovalently near the unmodified coenzyme. Epoxide ...

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Formation of epoxide intermediates in the reaction of enzyme-bound 5-deazaflavin with peroxides.

Reaction of free 5-deazaflavin with Hz02 or m-chloroperoxybenzoate results in the formation of 4a,5epoxy derivatives. These compounds (Arna 340 nm) are nonfluorescent, decompose in neutral aqueous solution, and react with iodide to regenerate the original parent compound. The initial reaction of peroxides with 5-deazaFAD bound to oxynitrilase or with 5-deazaFMN bound to glycolate oxidase result...

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Nucleophilic addition reactions of free and enzyme-bound deazaflavin.

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 th...

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Oxacycle Synthesis via Intramolecular Reaction of Carbanions and Peroxides

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ژورنال

عنوان ژورنال: Journal of Biological Chemistry

سال: 1983

ISSN: 0021-9258

DOI: 10.1016/s0021-9258(18)32093-3