Conversion of canavanine to α-keto-γ-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 James Cooper},
  journal={Archives of Biochemistry and Biophysics},
  year={1989},
  volume={270},
  pages={698-713}
}
Abstract 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 β,-γ-elimination reaction following enzymatic oxidation at the α-C and that the abstraction of the β-H is general-base catalyzed. The elimination reaction requires the presence in the α-position of an anion-stabilizing group—the protonated imino group (iminium ion… 
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