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N-Nitrosated N-Hydroxyguanidines Are Nitric Oxide-Releasing Diazeniumdiolates

Author:

Southan, G. J.

Srinivasan, A.

George, C.

Fales, H. M.

Keefer, L. K.

1. Year: 1998
Journal: Chemical Communications
1. Issue: 11
2. Pages: 1191-1192
Type of Article: Article

Abstract:

N-Hydroxyguanidines can be nitrosatively converted to zwitterionic diazeniumdiolates of crystallographically-confirmed structure H2N+=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 N-G-hydroxy-L-arginine (a metabolic intermediate in mammalian NO biosynthesis) to aerobic NO. [References: 11]

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