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Complexes of diphenylarsinic acid and phenylarsonic acid with thiols: a 1H and 13C NMR study

✍ Scribed by Takashi Nakayama; Tomohiko Isobe; Kunichika Nakamiya; John S. Edmonds; Yasuyuki Shibata; Masatoshi Morita

Publisher: John Wiley and Sons
Year: 2005
Tongue: English
Weight: 164 KB
Volume: 43
Category: Article
ISSN: 0749-1581
DOI: 10.1002/mrc.1585

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✦ Synopsis

Abstract

The high toxicity of diphenylarsinic acid, found in ground water and well water as a probable consequence of the inappropriate disposal of warfare agents, prompted us to study the reaction, monitored by ^1^H and ^13^C NMR spectroscopy, of the compound and its monophenyl analogue, phenylarsonic acid, with cellular thiols as represented, in particular, by glutathione. Glutathione reduced the phenylarsenic acids to trivalent forms and complexed them: diphenylarsinic acid to a monoglutathione adduct and phenylarsonic acid to a diglutathione adduct. The complexes were characterized by ^1^H and ^13^C NMR spectroscopy and mass spectrometry. The NMR spectra showed the diastereotopic nature of the two phenyl groups in the diphenylarsinic acid–glutathione compound, and of the two glutathione residues in the phenylarsonic acid–diglutathione complex. The stereochemistry of thiol compounds of phenylarsonic acid was further explored by ^1^H and ^13^C NMR spectroscopy of the L‐cysteine complex. The diphenylarsinic acid–glutathione complex was stable below pH 12 but at higher pH the complex dissociated into diphenylarsinous acid and reduced glutathione. The released diphenylarsinous acid then oxidized to diphenylarsinic acid with a half‐life of about 7 h at pH 13 and at room temperature. Copyright © 2005 John Wiley & Sons, Ltd.

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