• Corpus ID: 12993135

Conversion of canavanine to alpha-keto-gamma-guanidinooxybutyrate and to vinylglyoxylate and 2-hydroxyguanidine.

@article{Hollander1989ConversionOC,
  title={Conversion of canavanine to alpha-keto-gamma-guanidinooxybutyrate and to vinylglyoxylate and 2-hydroxyguanidine.},
  author={Marsha M. Hollander and A J Reiter and William H. Horner and Arthur J. L. Cooper},
  journal={Archives of biochemistry and biophysics},
  year={1989},
  volume={270 2},
  pages={
          698-713
        }
}
It was observed previously that hydroxyguanidine is formed in the reaction of canavanine(2-amino-4-guanidinooxybutanoate) with amino acid oxidases. The present work shows that hydroxyguanidine is formed by a nonenzymatic beta,gamma-elimination reaction following enzymatic oxidation at the alpha-C and that the abstraction of the beta-H is general-base catalyzed. The elimination reaction requires the presence in the alpha-position of an anion-stabilizing group--the protonated imino group (iminium…