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Two-dimensional NMR studies of arsenical-sulfhydryl adducts

✍ Scribed by Richard J. O'Connor; Evelyn L. McGown; Kilian Dill; Susan F. Hallowell

Publisher: John Wiley and Sons
Year: 1989
Tongue: English
Weight: 422 KB
Volume: 27
Category: Article
ISSN: 0749-1581
DOI: 10.1002/mrc.1260270713

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✦ Synopsis

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. 'H and ' ' C 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.

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