Abstract Peroxynitrite reacts with thiols 1 at acidic pH to give the corresponding S- nitrosothiols 2 and disulfides 3. The formation of nitrosothiols 2, the yield of which is strongly pH-dependent, can be rationalized in terms of acid-catalyzed decomposition of the undissociated HPN, probably through the intermediacy of the protonated form H 2 PN+, leading to a species, X− NO, capable of nitrosating the thiol function. In contrast, the ...
[Barrett, Anthony G.M.; Barton, Derek H.R.; Nagubandi, Sreemulu Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1980 , p. 237 - 239]