NMR and MS study of the formation of beta-D-glucopyranosylamine uronic acid in aqueous solution

作者：Ghadban Ali; Albertin Luca^*; Condamine Eric; Mounguengui Redeo W Moussavou; Heyraud Alain

来源：Canadian Journal of Chemistry, 2011, 89(8): 987-1000.

DOI：10.1139/V11-064

• uronic acids
• glycosylamines
• amination
• alpha anomer
• precursor

The products of the reaction of D-glucuronic acid with various combinations of ammonia and volatile ammonium salts in water were studied by NMR and MS spectroscopy. For long reaction times (similar to 24 h), the expected products beta-D-glucopyranosylamine uronic acid and ammonium N-(beta-D-glucopyranosyluronic acid)carbamate were obtained in good-to-high yield, whereas seven intermediate species were identified in samples taken at earlier reaction times. (1)H-(1)H homonuclear and (1)H-(13)C heteronuclear correlation experiments enabled a complete assignment of the (1)H and (13)C NMR spectra of the starting and final compounds, and a partial assignment of the peaks of intermediate species. Based on these results, a (1)H NMR protocol for the quantification of the different compounds taking part in the reaction was developed, which was used to monitor the evolution of the composition of an early reaction sample redissolved in D(2)O. It was thus established that two of the observed intermediate species are actually the alpha anomer of the main products, whereas the others are precursors to the formation of alpha/beta-D-glucopyranosylamine uronic acid and ammonium N-(alpha/beta-D-glucopyranosyluronic acid)carbamate. The correct assignments for the (1)H and (13)C spectra of D-glucuronic acid in D(2)O are also reported.

• 出版日期2011-8
• 单位中国地震局