Nitrite anion: the key intermediate in alkyl nitrates degradative mechanism.
Alkyl nitrates are metabolized in vitro to yield nitric oxide, and thiol groups have long been considered necessary cofactors. Here, we report evidence that no reaction between thiols and alkyl nitrates takes place in vitro, but stronger reducing agents, such as iron(II) derivatives, are necessary; alkoxy radicals and nitrite anions are the reaction intermediates. The latter, in slightly acidic conditions, can nitrosate thiols to the corresponding S-nitrosothiols, the real NO releasers.
Grossi
Loris
L
Dipartimento di Chimica Organica A Mangini, Università di Bologna, Bologna, Italy. loris.grossi@unibo.it
D000838:Anions; D002712:Chlorides; D005290:Ferric Compounds / Q000737:chemistry; D005296:Ferrous Compounds / Q000737:chemistry; D005609:Free Radicals / Q000737:chemistry; D005978:Glutathione / Q000737:chemistry; D009566:Nitrates / Q000737:chemistry*; D009573:Nitrites / Q000737:chemistry*; D010084:Oxidation-Reduction; D013438:Sulfhydryl Compounds / Q000737:chemistry*
D000838:Anions; D002712:Chlorides; D005290:Ferric Compounds; D005296:Ferrous Compounds; D005609:Free Radicals; D009566:Nitrates; D009573:Nitrites; D013438:Sulfhydryl Compounds; D005978:Glutathione; C029451:ferrous chloride; C024555:ferric chloride