Carbohydrate Research p. 15 - 30 (1992)
Update date:2022-08-11
Topics:
Vernin, Gaston
Metzger, Jacques
Boniface, Christian
Murello, Marie-Helene
Siouffi, Antoine
et al.
Fructose-methionine Amadori intermediates, prepared from D-glucose and L-methionine, were purified by semi-preparative HPLC.Structural elucidation was achieved by 13C-NMR and mass spectrometry in the FAB+ and FAB- modes.Constant rates of formation of glucosylamine and the Amadori intermediate, and their thermal degradation into reductones and methionine as well as into diglucosylamine, were observed.Thermal degradation of the Amadori intermediate gives not only the well-known degradation products of the sugar moiety and methional (from the Strecker degradation of methionine), but also several heterocyclic compounds (pyridines, pyrazines, pyrroles, and furans).Some of them contain a methylthiopropyl group in their side chain.These new compounds were identified by the fragmentation rules and Kovats additive properties.Out of the 80 compounds isolated, ca. 70 were identified.
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