S-nitrosothiols are thought to be important intermediates in nitric oxide signaling pathways. These compounds are unstable, in part, through their ability to donate NO. One model S-nitrosothiol, S-nitrosocysteine, is particularly unstable. Recently, it was proposed that this compound decomposed via intra and intermolecular transfer of the NO group from the sulfur to the nitrogen to form N-nitrosocysteine. This primary nitrosamine is expected to rapidly rearrange to ultimately form a reactive diazonium ion intermediate. To test this hypothesis, we demonstrated that thiirane-2-carboxylic acid is formed during the decomposition of S-nitrosocysteine at neutral pH. Acrylic acid was another product of this reaction. These results indicate that a small but significant amount of S-nitrosocysteine decomposes via S- to N-transnitrosation. The formation of a reactive intermediate in this process indicates the potential for this reaction to contribute to the toxicological properties of nitric oxide.
Decomposition of S-nitrosocysteine via S- to N-transnitrosation. Publishing Authors By Initials
Decomposition of S-nitrosocysteine via S- to N-transnitrosation. Journal Published:
PUBLICATION TYPE: Research Support, Non-U.S. Gov
Journal: Chemical research in toxicology
VOLUME: 20
Page Numbers: 721-3
Journal Abbreviation: Chem. Res. Toxicol.
ISSN: 0893-228X
DAY: 18
MONTH: 04
YEAR: 2007
Decomposition of S-nitrosocysteine via S- to N-transnitrosation. Information
Number of References:
LANGUAGE: eng
NlmUniqueID: 8807448
Decomposition of S-nitrosocysteine via S- to N-transnitrosation. Keywords Mesh Terms:
KEYWORDS: Sulfur
MESH TERMS: chemistry
Chemical & Substance for Abstract: Decomposition of S-nitrosocysteine via S- to N-transnitrosation. Information
Substance Name: acrylic acid
Registry Number: 79-10-7
Grant and Affiliation Information for Decomposition of S-nitrosocysteine via S- to N-transnitrosation.
AFFILIATION: Division of Environmental Health Sciences and the Cancer Center, University of Minnesota, Minneapolis, Minnesota 55455, USA. peter431@umn.edu
Country: United States
AGENCY: United States NCI
GRANT: CA59887
ACRONYM: CA
MEDLINETA: Chem Res Toxicol
REFSOURCE:
DATABASENAME:
ACCESSION NUMBER:
Number Hits: 0
Decomposition of S-nitrosocysteine via S- to N-transnitrosation Related Publications