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KMID : 0370019900040000106
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Chung-Ang Journal of Pharmacal Sciences
1990 Volume.4 No. 0 p.106 ~ p.114
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Synthesis and Characterization of Isotopically-Labelled Cystenine and Glutathione Conjugates of Methylisocyanate
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Han, Deog Hwa/Department of Medicinal Chemistry, School of Pharmacy, BG-20, University of Washington
Person, Paul G/Baillie Thomas A./Department of Medicinal Chemistry, School of Pharmacy, BG-20, University of Washington/Department of Medicinal Chemistry, School of Pharmacy, BG-20, University of Washington
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Abstract
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Four isotopically labelled analogs of S-(N-methylcarbamoyl) glutathione(SMG), the glutathione conjugate of methylisocyanate, and three isotopically-labelled derivatives of S-(N-methylcarbamoyl) cysteine (SMC), the corresponding cysteine adduct, have been prepared by reaction of glutathione and cysteine, respectively, with [1-^13C]-, [3-^13C]-, [3-14^C]- or [3, 3, 3-^2H_3]methylisocyanate. The latter species, which served as key intermediates in the syntheses, were obtained either by reaction of [1-^13C]acetylchloride with sodium azide [to give [1-^13C]methylisocyanate), or by reaction of silver cyanate with iodomethane labelled with ^13C, ^14C or deterium (to give the methyl-substituted compounds). Condensation of labelled methylisocyanate with glutathione or cysteine proceeded smoothly and in high yield in aqueous acetonitrile solution, and afforded the target conjugates in high isotopic purity. The structures of the products were confirmed by fast atom bombardment tandem mass spectrometry (FAB / MS / MS) and by ^1H- and ^13C-NMR spectroscopy.
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KEYWORD
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