1,5-Anhydro-D-fructose, a New Material for Modification of Amino Groups as Demonstrated Using Amino Acid and Proteins.

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1, 5-Anhydro-D-fructose (1, 5-anhydro-D-arabino-hexo-2-close, 1, 5-AF) reacted well with the amino group and seemed to be useful as a reagent for modification of the amino compounds. The rate of browning of 1, 5-AF by reaction with glycine was higher than those of glucose and xylose at 50°C and pH 7.5. Forty-five percent of the amino group of glycine was modified by the incubation of a lyophilized mixture of 1, 5-AF and glycine at 30°C for 48 h, whereas the degree of modification by glucose was less than 5%. This modification was applied to lysozyme. A mass spectrum indicated that the sugar moiety was incorporated into the lysozyme. The optimum pH values of the modified and unmodified lysozyme on glycolchitin were pH 4.5 and 5.0, respectively. On the other hand, the optimum pH of the modified enzyme on freeze-dried cells of Micrococcus lysodeikticus shifted from pH 7.8 to 6.0. Wheat proteins, gliadin and glutenin, were also modified. The modified gliadin had higher emulsification ability and solubility than the unmodified ones.