Two-Dimensional NMR Studies of Arsenical-Sulfhydryl Adducts

Article abstract of DOI:10.1002/mrc.1260270713

British anti-lewisite (2,3-dimercaptopropanol) (BAL) has long been used as an arsenic antidote, but its therapeutic efficacy is limited by its inherent toxicity.Two less toxic potential replacements for BAL are dimercaptosuccinic acid and dimercaptopropanesulfonic acid.These two disulfhydryl compounds were compared with BAL by studying the structures of their adducts with two organic arsenicals, phenyldichloroarsine and trans-2-chlorovinylarsine oxide.The 1:1 adducts were synthesized and characterized by one- and two-dimensional NMR spectroscopy. 1H and 13C spectral data and resonance assignments, verified by spin simulation, are presented for the adducts.All were five-membered heteroatomic ring systems, with different solubility properties.When stereoisomers were detectable, the ratio of anti to syn isomers varied, indicating that the functional group of the antidote influenced stereochemical aspects of adduct formation.KEY WORDS - 2D NMR Phenyldichloroarsine Lewisite British anti-lewisite Dimercaptosuccinic acid 2,3-Dimercaptopropanesulfonic acid Adducts