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Chemistry Of N-hydroxy-L-arginine.

J. Fukuto
Published 1996 · Chemistry, Medicine

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Abstract The synthesis of N -hydroxy- l -arginine can be accomplished by a relatively simple and straightforward procedure. Also, a variety of arginine derivatives can be synthesized using minor modifications of this procedure. N -Hydroxy- l -arginine is subject to decomposition under either basic or oxidizing conditions. In fact, one of the dominant chemical features of N -hydroxy- l -arginine (or N -hydroxyguanidines), which would be significant to those interested in exploring its role either as a biosynthetic intermediate in NO generation or as an independently acting species, is its ability to act as a reducing agent. Even a cursory inspection of N -hydroxy- l -arginine indicates that the N -hydroxyguanidine function is electron rich and could be easily oxidized. Oxidation of N -hydroxy- l -arginine is, indeed, facile and can lead to either the release of HNO (from a two-electron oxidation) or the formation of an apparent radical species (from one-electron oxidation). The ability of N -hydroxy- l -arginine to act as a one-electron reducing agent (or hydrogen atom-donor) may be important in the biosynthesis of the NO radical since an odd-electron step is required. 17 Regardless, it is likely that N -hydroxyguanidines can act as electron sources and may participate in redox reactions with biological oxidants. The physiological relevance of such processes, however, remains to be determined.
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