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The SH bond of thiols dissociates with pKa (pH where 50% dissociated) in the range ~ 710:RSH RS + H+thiolpKaH2S ~71 (to form HS)cysteine ~85, 89 (-NH3+, -NH2) glutathione ~89, 91 (-NH3+, -NH2) About 3% of glutathione (GSH) is dissociated to the thiolate form (GS) at pH 74 Many reactions of thiols with oxidants will be pH-dependent around physiological pH because the thiolate form is usually oxidized much faster than the undissociated thiol Effects of thiol dissociation on rates of reactions in the physiological pH range Example of thiolate(pH)-dependent reactivity Reactivity of GSH increased exactly 100fold between pH 68 Acetaminophen (paracetamol, Tylenol) oxidized in the liver to a quinoneimine GSH adds rapidly to double bond, protects against adduct forming with protein thiols Only thiolate anion reactive, reaction pH-dependent at pH 10 107 (Folkes et al
Obulesu M, Lakshmi MJ (2014) Apoptosis in Alzheimers disease: an understanding of the physiology, pathology and therapeutic avenues
10.1183/16000617.0001-2024 47 MthotN.RubinJ.GuayD.BeaulieuC.EthierD.ReddyT
not independently peer-reviewed by Astral
Funding Statement The study was supported by Heilongjiang Provincial Clinical Collaboration Project for Major and Difficult Diseases Integrating Traditional Chinese and Western Medicine, and Longjiang scholar support program (15991190005)
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