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E. S. C. BEUGRE, Dept. of Food Science, McGill university, Macdonald campus, Sainte Anne de Bellevue, QC H9X 3V9, Canada

In thermally processed foods, Amadori products are considered to be critical for the generation of flavors and colors. During their solvent phase synthesis, these reactive precursor forms decompose and polymerize into brown polymers and hence are difficult to isolate from the reaction mixtures in high yields. Solid phase synthesis of Amadori products is a convenient and attractive alternative for synthesis where the sugar and the amino compound can be reacted, while one of the reactants is immobilized on an insoluble support.

Our objective was to develop a solid phase synthesis of flavor precursor 1-(amino acid)-1-deoxy-D-fructose derivatives.

The chloromethyl divinylbenzen copolymer was converted to a divinylbenzaldehyde-styrene copolymer, and then reacted with glucose to form 4,6-O-benzylidene glucose-styren copolymer. This immobilized glucose was condensed to N-amylamine, washed with 20% CF₃COOH to cleave the Amadori products and regenerate the solid support.

The infrared spectra showed the appearance of a large peak at 1700^cm-1 attributed to the aldehydic carbonyl group(C=O) proving that the chloromethyl divinylbenzen-styrene copolymer was converted to divinylbenzaldehyde-styrene copolymer. (yields were 48.30g; 0.79 mmol of CHO/g of resin). The presence of characteristic sugar's peaks absorption hydroxyl bands (OH) at 1288, 1080 and 1047^cm-1 indicate the effectiveness of the sugar addition. The condensation of N-amylamine to the polymer protected sugar shows the disappearance of the large C=O band at 1700^cm-1 and the appearance of a large peak at 1644^cm-1 suggesting a new mechanism. After acid hydrolysis, Amadori products were revealed by the Elson-Morgan test.

These results suggest that the polymer supported synthesis has the advantage of producing flavor precursors in gram quantities.