Correlations between Structure and Reactivity of Amadori Compounds: the Reactivity of Acyclic Forms

Summary Several Amadori compounds were prepared and solution (NMR) and, in some cases, solid-state structures (X-ray) were determined. Several of the compounds studied contain sugar units which exist predominantly in acyclic forms. Such compounds were used as model Amadori compounds and rates of reactivity with respect to C(1)H2 proton exchange, the ability to generate oxygen free radicals, and the type of dicarbonyl intermediates produced were evaluated. The results of the experiments enable direct, although qualitative, correlations to be made between the population of acyclic forms in solutions of Amadori compounds, the rates of their reversible enolization, and their reactivity in redox and degradation reactions.