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Synthesis and characterization of isotopically‐labelled cysteine‐ and glutathione conjugates of methylisocyanate
Author(s) -
Han DeogHwa,
Pearson Paul G.,
Baillie Thomas A.
Publication year - 1989
Publication title -
journal of labelled compounds and radiopharmaceuticals
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.432
H-Index - 47
eISSN - 1099-1344
pISSN - 0362-4803
DOI - 10.1002/jlcr.2580271204
Subject(s) - chemistry , glutathione , cysteine , adduct , fast atom bombardment , mass spectrometry , conjugate , isotopic labeling , nuclear magnetic resonance spectroscopy , stereochemistry , organic chemistry , chromatography , mathematical analysis , mathematics , enzyme
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‐ 13 C]‐, [3‐ 13 C]‐, [3‐ 14 C]‐ or [3,3,3‐ 2 H 3 ]methylisocyanate. The latter species, which served as key intermediates in the syntheses, were obtained either by reaction of [1‐ 13 C]acetylchloride with sodium azide (to give [1‐ 13 C]methylisocyanate), or by reaction of silver cyanate with iodomethane labelled with 13 C, 14 C or deuterium (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 1 H‐ and 13 C‐NMR spectroscopy.