L-Arginine N-hydroxy

Scheme 7.13 Nitric oxide synthase-mediated conversion of N-hydroxy-L-arginine to nitric oxide.

Wallace, G. C., Gulati, P., and Fukuto, J. M. (1991). N -Hydroxy-L-arginine A novel arginine analog capable of causing vasorelaxation in bovine intrapulmonary artery. Biochem. Biophys. Res. Commun. 176, 528-534. 

Pufahl, R. A., and Marietta, M. A. (1993). Oxidation of N -Hydroxy-L-arginine by nitric oxide synthase Evidence for the involvement of the heme in catalysis. Biochem. Biophys. Res. Commun. 193, 963-970. 

Widmer, J., and Keller-Schierlein, W. (1974). Metabolites of microorganisms. 130. Synthesis of delta-N-hydroxy-L-arginine. Helv. Chim. Acta 57, 657-664. 

Boucher, J.-L., Genet, A., Vadon, S., Delaforge, M., Henry, Y., and Mansuy, D. (1992). Cytochrome P450 catalyzes the oxidatit)n of N - -hydroxy-L-arginine by NADPH and O2 to nitric oxide and citrulline. Biochem. Biophys. Res. Commun. 187, 880-886. 

All NOS isoforms catalyse the hydroxylation of L-arginine to form N°-hydroxy-L-arginine, which is subsequently converted to L-citrulline and NO (Fig. (4)). This reaction requires molecular oxygen (O2) and NADPH. 

Klatt, P., Schmidt, K., Uray, G., and Mayer, B. (1993). Multiple catalytic functions of brain nitric oxide synthase. Biochemical characterization, cofactor-requirement and role of N "-hydroxy-L-arginine as an intermediate. J. Biol. Chem. 268, 14781-14787. 

Free N-hydroxyamino acids (1) or (2) have never been isolated from living organisms, probably because of their instability. As already mentioned, N-hydroxyamino acid residues occur only as fragments of many natural products containing the N-hydroxyamide bond. The isolation of free N -hydroxy-L-arginine from the fermentation medium of Bacillus cereus (6, 7) may be considered as an exception however, this compound contains an N-hydroxyguanidine rather than an N-hydroxyamine group. 

Fischer, B., W. Keller-Schierlein, H. Kneifel, W.A. Konig, W. Loeffler, A. Muller, R. Muntwyler, and H. Zahner Stoffwechselprodukte von Mikroor-ganismen. 118. S-N-Hydroxy-L-arginin, ein Aminosaure-Antagonist aus Nannizzia grypsea. Arch. Mikrobiol. 91, 203 (1973). 

Maehr, H., J.F. Blount, D.L. Pruess, L.Yarmchuk, and M. Kellett Antimetabolites Produced by Microorganisms. VIII. N -Hydroxy-L-arginine, a New Naturally Occuring Amino Acid. J. Antibiotics 26, 284 (1973). 

Perlman, D., A.J. Vlietinck, H.W. Matthews, and F.F. Lo Microbial Production of Vitamin B12 Antimetabolites. I. N -Hydroxy-L-arginine from Bacillus cereus 439. 

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