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The autoxidation of 3-hydroxyanthranilic acid in the presence of amino acids

Journal Article


Abstract


  • The autoxidation of 3-hydroxyanthranilic acid 1 at pH 11.7 in the presence of the amino acids lysine, glycine and alanine gave p-quinone conjugates. The autoxidation of 1 in the presence of proline gave two rearrangement products arising from Strecker degradation of the initially formed proline conjugate. N-α-t-Boc histidine, arginine and cysteine failed to give amino acid conjugates with oxidized 1. © 1989.

Publication Date


  • 1989

Citation


  • Manthey, M. K., Pyne, S. G., & Truscott, R. J. W. (1989). The autoxidation of 3-hydroxyanthranilic acid in the presence of amino acids. Tetrahedron, 45(9), 2803-2810. doi:10.1016/S0040-4020(01)80110-1

Scopus Eid


  • 2-s2.0-38249024787

Web Of Science Accession Number


Start Page


  • 2803

End Page


  • 2810

Volume


  • 45

Issue


  • 9

Abstract


  • The autoxidation of 3-hydroxyanthranilic acid 1 at pH 11.7 in the presence of the amino acids lysine, glycine and alanine gave p-quinone conjugates. The autoxidation of 1 in the presence of proline gave two rearrangement products arising from Strecker degradation of the initially formed proline conjugate. N-α-t-Boc histidine, arginine and cysteine failed to give amino acid conjugates with oxidized 1. © 1989.

Publication Date


  • 1989

Citation


  • Manthey, M. K., Pyne, S. G., & Truscott, R. J. W. (1989). The autoxidation of 3-hydroxyanthranilic acid in the presence of amino acids. Tetrahedron, 45(9), 2803-2810. doi:10.1016/S0040-4020(01)80110-1

Scopus Eid


  • 2-s2.0-38249024787

Web Of Science Accession Number


Start Page


  • 2803

End Page


  • 2810

Volume


  • 45

Issue


  • 9