Online citations, reference lists, and bibliographies.
← Back to Search

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, D. Stuehr, P. Feldman, M. Bova, P. Wong
Published 1993 · Chemistry, Medicine

Cite This
Download PDF
Analyze on Scholarcy
Share
Arginine is oxidized by a class of enzymes called the nitric oxide synthases (NOS) to generate citrulline and, presumably, nitric oxide (.NO). N-Hydroxylation of a guanidinium nitrogen of arginine to generate N-hydroxyarginine (NOHA) has been shown to be a step in the biosynthesis of .NO. In an effort to elucidate the mechanism by which further oxidation of NOHA occurs, the oxidation of a model N-hydroxyguanidine compound by several peracids was studied in depth. This oxidative chemistry is a possible model for the enzymatic process since the corresponding urea (or citrulline equivalent product) is obtained along with an oxidized nitrogen species. The oxidized nitrogen product was, however, not .NO but rather HNO. .NO generation in this chemical system and in the enzymatic process would require another one-electron oxidation. The mechanistic details of this are further discussed.



This paper is referenced by
10.1016/J.CRVI.2004.12.002
Production of NA by endothelial NO-synthase: an in vitro versus in vivo study.
A. Meulemans (2005)
10.1007/978-1-4615-1903-4_2
Mechanisms of Mammalian Nitric Oxide Biosynthesis
P. Feldman (1995)
10.1146/ANNUREV.PHARMTOX.45.120403.095959
Nitroxyl (HNO): chemistry, biochemistry, and pharmacology.
J. Fukuto (2005)
10.1046/J.1432-1033.2003.03358.X
Microperoxidase 8 catalysed nitrogen oxides formation from oxidation of N-hydroxyguanidines by hydrogen peroxide.
R. Ricoux (2003)
10.1007/978-3-0348-8747-2_2
Inducible nitric oxide synthase and inflammation
A. Hobbs (1999)
MOLECULAR REGULATION OF ENDOTHELIAL NITRIC OXIDE SYNTHASE
P. Lane (2000)
10.1016/S0006-2952(99)00102-1
Microsomal formation of nitric oxide and cyanamides from non-physiological N-hydroxyguanidines: N-hydroxydebrisoquine as a model substrate.
B. Clement (1999)
10.1016/S0003-9861(03)00335-7
Oxidation of N-hydroxyguanidines by copper(II): model systems for elucidating the physiological chemistry of the nitric oxide biosynthetic intermediate N-hydroxyl-L-arginine.
J. Cho (2003)
10.1016/S0003-9861(02)00729-4
Differential effects of mutations in human endothelial nitric oxide synthase at residues Tyr-357 and Arg-365 on L-arginine hydroxylation and GN-hydroxy-L-arginine oxidation.
P. Chen (2003)
Molecular investigation of candidate genes involved in the biosynthesis of dinoflagellate paralytic shellfish toxins
L. Harlow (2005)
10.1016/S0960-894X(00)00345-0
Metalloporphyrin catalyzed oxidation of N-hydroxyguanidines: a biomimetic model for the H2O2-dependent activity of nitric oxide synthase.
G. Keserű (2000)
10.1089/ARS.2006.8.1363
The activation of metabolites of nitric oxide synthase by metals is both redox and oxygen dependent: a new feature of nitrogen oxide signaling.
Sonia Donzelli (2006)
10.1016/0040-4039(95)01242-A
Superoxide anion efficiently performs the oxidative cleavage of CNOH bonds of amidoximes and N-hydroxyguanidines with formation of nitrogen oxides
N. Sennequier (1995)
10.1074/JBC.275.12.8582
Unusual Oxidative Chemistry ofN ω-Hydroxyarginine and N-Hydroxyguanidine Catalyzed at an Engineered Cavity in a Heme Peroxidase*
J. Hirst (2000)
10.1016/S0891-5849(98)00120-8
Hydroxyguanidines inhibit peroxynitrite-induced oxidation.
G. Southan (1998)
10.1016/S0166-1280(98)00573-9
Lewis acidity of NO+ and NO2+ as measured by their affinity to selected bases. An ab initio background study of biological NO release
L. L. Torday (1999)
Developing Detection Methods for Nitroxyl
Gail M Johnson (2013)
10.1039/c0ob01117g
Prodrug design for the potent cardiovascular agent Nω-hydroxy-L-arginine (NOHA): synthetic approaches and physicochemical characterization.
D. Schade (2011)
10.1016/J.FREERADBIOMED.2004.06.031
Alternative nitric oxide-producing substrates for NO synthases.
D. Mansuy (2004)
10.1021/ja312092x
Nitrite reduction mediated by heme models. Routes to NO and HNO?
Julie L Heinecke (2013)
10.1016/S0076-6879(96)68039-2
Chemistry of N-hydroxy-L-arginine.
J. Fukuto (1996)
10.1039/c5dt03459k
Mechanistic studies of the reactions of the reduced vitamin B12 derivatives with the HNO donor Piloty's acid: further evidence for oxidation of cob(I)alamin by (H)NO.
Harishchandra Subedi (2016)
10.1016/S0166-1280(98)00497-7
A conformational study on the intermediates along the synthetic pathway of nitric oxide (NO) formation by NO synthase
M. B. Santillán (1999)
10.1002/(SICI)1521-3757(19990614)111:12<1824::AID-ANGE1824>3.0.CO;2-E
Stickstoffmonoxid: die rätselhafte Chemie eines biologischen Botenstoffes
S. Pfeiffer (1999)
10.1074/jbc.M004337200
Arginine Conversion to Nitroxide by Tetrahydrobiopterin-free Neuronal Nitric-oxide Synthase
S. Adak (2000)
10.1016/j.saa.2020.118680
A near-infrared fluorescent probe for imaging of nitroxyl in living cells.
Z. Liu (2020)
10.1089/ars.2010.3841
The specificity of nitroxyl chemistry is unique among nitrogen oxides in biological systems.
Wilmarie Flores-Santana (2011)
10.1002/JCCS.199800083
A GENERAL PROCEDURE FOR SYNTHESIS OF NG-ALKYL, AND NG-ARYL-L-ARGININES AS POTENTIAL NITRIC OXIDE SYNTHASE INHIBITORS
B. Chen (1998)
Nitric oxide in acute and chronic inflammation
M. Paul-Clark (2002)
10.1007/s12039-014-0751-4
Efficient iron(III) porphyrins-catalyzed oxidation of guanidoximes to cyanamides in ionic liquids
P. Kumari (2015)
10.1016/S0166-1280(99)00031-7
A MODEL MECHANISM OF NITRIC OXIDE (NO) FORMATION BY NO SYNTHASE
M. B. Santillán (1999)
10.1089/152308603322110887
Heme proteins and nitric oxide (NO): the neglected, eloquent chemistry in NO redox signaling and regulation.
D. Thomas (2003)
See more
Semantic Scholar Logo Some data provided by SemanticScholar