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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.
This paper references
10.1039/C39880001618
Ester bio-isosteres: synthesis of oxadiazolyl-1-azabicyclo[2.2.1]heptanes as muscarinic agonists
J. Saunders (1988)
10.1016/S0040-4039(00)92109-9
Synthesis of the putative l-arginine metabolite L-NG-hydroxyarginine
P. Feldman (1991)
10.1021/BI00144A024
Mechanistic probes of N-hydroxylation of L-arginine by the inducible nitric oxide synthase from murine macrophages.
R. A. Pufahl (1992)
10.1021/JM00070A010
Peracid oxidation of an N-hydroxyguanidine compound: a chemical model for the oxidation of N omega-hydroxyl-L-arginine by nitric oxide synthase.
J. Fukuto (1993)
10.1007/978-3-642-85055-4
The Practice of Peptide Synthesis
Professor Dr. Miklos Bodanszky (1994)
10.1021/JO00068A031
Methodology for the preparation of N-guanidino-modified arginines and related derivatives
F. Wagenaar (1993)
10.1021/BI00006A014
Hydrogen peroxide-supported oxidation of NG-hydroxy-L-arginine by nitric oxide synthase.
R. A. Pufahl (1995)
Multiple catalytic functions of brain nitric oxide synthase. Biochemical characterization, cofactor-requirement, and the role of N omega-hydroxy-L-arginine as an intermediate.
P. Klatt (1993)
A self-consistent field molecular orbital study of hydroxyguanidine.
A. M. Sapse (1981)
10.1016/0006-291X(91)90957-9
N omega-hydroxy-L-arginine: a novel arginine analog capable of causing vasorelaxation in bovine intrapulmonary artery.
G. C. Wallace (1991)
10.1021/JM00368A024
Novel N-hydroxyguanidine derivatives as anticancer and antiviral agents.
A. Tai (1984)
10.1016/0006-2952(92)90584-6
Chemical oxidation of N-hydroxyguanidine compounds. Release of nitric oxide, nitroxyl and possible relationship to the mechanism of biological nitric oxide generation.
J. Fukuto (1992)
10.1038/236400A0
Biological Sciences: Hydroxyguanidine—a New Antitumour Drug
R. Adamson (1972)
10.1006/BBRC.1994.1909
Inhibition of rat liver arginase by an intermediate in NO biosynthesis, NG-hydroxy-L-arginine: implications for the regulation of nitric oxide biosynthesis by arginase.
F. Daghigh (1994)
10.1021/JM00109A032
Synthesis and bioactivity of N omega-hydroxyarginine: a possible intermediate in the biosynthesis of nitric oxide from arginine.
G. C. Wallace (1991)
10.1016/0006-2952(93)90616-5
Cytochrome P450 dependent N-hydroxylation of a guanidine (debrisoquine), microsomal catalysed reduction and further oxidation of the N-hydroxy-guanidine metabolite to the urea derivative. Similarity with the oxidation of arginine to citrulline and nitric oxide.
B. Clement (1993)
On the mechanism of the nitric oxide synthase-catalyzed conversion of N omega-hydroxyl-L-arginine to citrulline and nitric oxide.
H. Korth (1994)
N omega-hydroxy-L-arginine is an intermediate in the biosynthesis of nitric oxide from L-arginine.
D. Stuehr (1991)



This paper is referenced by
10.1021/ja906133h
EPR and ENDOR characterization of the reactive intermediates in the generation of NO by cryoreduced oxy-nitric oxide synthase from Geobacillus stearothermophilus.
R. Davydov (2009)
10.1135/CCCC20040499
Nω-Hydroxy-L-arginine and Its Homologues. Chemical and Biological Properties. A Review
Petra Beranová (2004)
Abgrenzung der verschiedenen Schadensersatzansprüche
Long Jiang (2001)
10.11606/D.60.2009.tde-10092009-085526
Análise in vitro e in vivo da ação conjunta dos hormônios Dehidroepiandrosterona (DHEA) e Melatonina (MEL) contra Trypanosoma cruzi
C. C. Kuehn (2009)
10.5445/IR/1000084228
Spektroskopische Untersuchungen an der induzierbaren Stickstoffmonoxid-Synthase (iNOS)
M. Horn (2018)
10.1007/978-3-7091-6351-1_1
Nitric oxide: physiological roles, biosynthesis and medical uses.
D. R. Adams (1999)
10.1016/j.pharmthera.2010.02.005
Modulating the NO generating system from a medicinal chemistry perspective: current trends and therapeutic options in cardiovascular disease.
D. Schade (2010)
Fourier transform infrared spectroscopy study of ligand photodissociation and migration in inducible nitric oxide
Nienhaus (2014)
10.1021/jm401977j
Oseltamivir analogues bearing N-substituted guanidines as potent neuraminidase inhibitors.
Caitlin A. Mooney (2014)
10.1016/j.niox.2008.04.016
Nitric oxide, N omega-hydroxy-L-arginine and breast cancer.
S. Pervin (2008)
10.1016/j.jinorgbio.2012.09.024
Oxidation of N-hydroxy-l-arginine by hypochlorous acid to form nitroxyl (HNO).
Meredith R. Cline (2013)
10.1016/j.abb.2010.02.004
Inhibition of human arginase I by substrate and product analogues.
L. Di Costanzo (2010)
10.1039/c0ob01117g
Prodrug design for the potent cardiovascular agent Nω-hydroxy-L-arginine (NOHA): synthetic approaches and physicochemical characterization.
D. Schade (2011)
10.12688/f1000research.5836.1
Fourier transform infrared spectroscopy study of ligand photodissociation and migration in inducible nitric oxide synthase.
M. Horn (2014)
10.12688/f1000research.5836.2
Fourier transform infrared spectroscopy study of ligand photodissociation and migration in inducible nitric oxide synthase
Michael Dr. Horn (2014)
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