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DOI: 10.1039/A801543K (Paper) Reference Section for: Chem. Commun., 1998, 1191-1192

N-Nitrosated N-hydroxyguanidines are nitric oxide-releasing diazeniumdiolates

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Garry J. Southan, Aloka Srinivasan, Larry K. Keefer, Clifford George and Henry M. Fales

Abstract

N-Hydroxyguanidines can be nitrosatively converted to zwitterionic diazeniumdiolates of crystallographically-confirmed structure H2N+[double bond, length half m-dash]C[NHR][N(O)NO]–, whose hydrolytic dissociation at physiological pH leads to both NO and N2O; the results appear to account for the formation of the ‘potential intercellular nitric oxide carrier’ produced on exposing NG- hydroxy-L-arginine (a metabolic intermediate in mammalian NO biosynthesis) to aerobic NO.

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