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Carbon disulfide is an environmental toxin, but there are suggestions in the literature that it may also have regulatory and/or therapeutic roles in mammalian physiology. Thiols or thiolates would be likely biological targets for an electrophile, such as CS 2 , and in this context, the present study examines the dynamics of CS 2 reactions with various thiols (RSH) in physiologically relevant near-neutral aqueous media to form the respective trithiocarbonate anions (TTC - , also known as "thioxanthate anions"). The rates of TTC - formation are markedly pH-dependent, indicating that the reactive form of RSH is the conjugate base RS - . The rates of the reverse reaction, that is, decay of TTC - anions to release CS 2 , is pH-independent, with rates roughly antiparallel to the basicities of the RS - conjugate base. These observations indicate that the rate-limiting step of decay is simple CS 2 dissociation from RS - , and according to microscopic reversibility, the transition state of TTC - formation would be simple addition of the RS - nucleophile to the CS 2 electrophile. At pH 7.4 and 37 °C, cysteine and glutathione react with CS 2 at a similar rate but the trithiocarbonate product undergoes a slow cyclization to give 2-thiothiazolidine-4-carboxylic acid. The potential biological relevance of these observations is briefly discussed.

Biological Thiols and Carbon Disulfide: The Formation and Decay of Trithiocarbonates under Physiologically Relevant Conditions