Reaction between S-Nitrosothiols and Thiols:  Generation of Nitroxyl (HNO) and Subsequent Chemistry

• Published in: Biochemistry (Easton) Vol. 37; no. 16; pp. 5362 - 5371
• Main Authors: Wong, Patrick S.-Y, Hyun, Jinjoo, Fukuto, Jon M, Shirota, Frances N, DeMaster, Eugene G, Shoeman, Don W, Nagasawa, Herbert T
• Format: Journal Article
• Language: English
• Published: United States American Chemical Society 21.04.1998
• Subjects: Aerobiosis; Ammonia - metabolism; Antioxidants - chemistry; Antioxidants - metabolism; Free Radicals - chemistry; Free Radicals - metabolism; Glutathione - analogs & derivatives; Glutathione - chemistry; Nitric Oxide - chemistry; Nitrites - metabolism; Nitrogen Oxides - chemistry; Nitrogen Oxides - metabolism; Nitroso Compounds - chemistry; Nitrous Oxide - metabolism; Oxidation-Reduction; S-Nitrosoglutathione; Sulfhydryl Compounds - chemistry
• ISSN: 0006-2960; 1520-4995
• DOI: 10.1021/bi973153g

S-Nitrosothiols have been implicated to play key roles in a variety of physiological processes. The potential physiological importance of S-nitrosothiols prompted us to examine their reaction with thiols. We find that S-nitrosothiols can react with thiols to generate nitroxyl (HNO) and the corresponding disulfide. Further reaction of HNO with the remaining S-nitrosothiol and thiol results in the generation of other species including NO, sulfinamide, and hydroxylamine. Mechanisms are proposed that rationalize the observed products.