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Proceedings of the National Academy of Sciences of the United States of America logoLink to Proceedings of the National Academy of Sciences of the United States of America
. 1976 Apr;73(4):995–999. doi: 10.1073/pnas.73.4.995

Simple synthesis of a 4a-hydroperoxy adduct of a 1,5-dihydroflavine: preliminary studies of a model for bacterial luciferase.

C Kemal, T C Bruice
PMCID: PMC430184  PMID: 1063419

Abstract

The solution chemistry of N(5)-alkyl flavinium cations and radical species formed by their le- reduction are discussed. Previously unknown, the 4a-flavine hydroperoxides are established to be formed on reaction of N(5)-alkyl flavinium cations with H2O2 or on reaction of N(5)-alkyl-1, 5-dihydroflavines with 3O2. The stability of the 4a-flavine hydroperoxide species is exemplified in the isolation and characterization of 4a-hydroperoxy-N(5)-ethyl-3-methyl-lumiflavine. 4a-Flavine hydroperoxide compounds are shown to be stronger oxidants than H2O2, and to undergo a chemiluminescent reaction in the presence of an aldehyde. Preliminary observations on the chemiluminescent reaction of 4a-flavine hydroperoxides + RCHO are provided, and these are compared to those in the literature dealing with the bioluminescence of bacterial luciferase in the presence of 3O2 and RCHO.

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Selected References

These references are in PubMed. This may not be the complete list of references from this article.

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