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Oxidation of amino-containing disulfides by Br/sub 2//sup -/ and OH: a pulse-radiolysis study. [1. 5 MeV electrons]

Journal Article · · J. Phys. Chem.; (United States)
DOI:https://doi.org/10.1021/j150601a016· OSTI ID:6603457

The rate constant for reaction of Br/sub 2/ radicals with dithiodipropionic acid (approx. 4.2 x 10/sup 8/ mol/sup -1/dm/sup 3/s/sup -1/) was independent of pH in the range 6.6-11.0 and was approx. 4.5 times smaller than those for the neutral dimethyl and diethyl disulfides Br/sub 2//sup -/ only reacted with the disulfides of cysteamine, cysteine, and penicillamine with an appreciable rate (> 10/sup 8/mol/sup -1/dm/sup 3/s/sup -1/) when one or both of the amino groups were unprotonated. Homocystine was less sensitive to the degree of protonation. While the reaction of Br/sub 2/ radicals with dithiodipropionic acid yielded a transient (lambda/sub max/ approx. = 450 nm) which possessed the characteristics of a disulfide cation, the amino-containing disulfides cited above produced transients which adsorbed with a lambda/sub max/ near 380 nm. The latter transients decayed by second-order kinetics over the pH range studied, and they gave no evidence of reaction with OH/sup -/. These species have been tentatively identified as perthiyl (RSS.) radicals. Hydroxyl radicals produced composite spectra consisting of the 380-nm species and other transients which absorbed below 350 nm. Oxidized glutathione gave only weak absorptions on reaction with Br/sub 2/ and OH radicals. The yields of sulfydryl molecules have been measured for cystine and dithiodipropionic acid. The mechanisms of radiolysis are discussed in the light of present results and earlier studies.

Research Organization:
Univ. of Calgary, Alberta
OSTI ID:
6603457
Journal Information:
J. Phys. Chem.; (United States), Journal Name: J. Phys. Chem.; (United States) Vol. 85:1; ISSN JPCHA
Country of Publication:
United States
Language:
English