糖-アミノ酸結合体の研究 (第1報)

6-O-グリシル-D-グルコースの合成とその性質について

抄録

The present series of work was carried out in order to obtain fundamental knowledge on the compounds formed by peptide bonded to sugar in vivo, more specifically the ester-type bonding in which the hydroxyl group of the sugar is bonded to carboxyl in the amino acid. For this purpose, examination was made on the preparation of 6-glycylglucose, the representative compound of the most simple monosaccharide and amino acid, and the object was attained in the following manner:
1, 2;3, 5-Di-O-benzylidene-D-glucofuranose was reacted with N-benzyloxycarbonylglycine, used as reagent for peptide synthesis, and diethylphosphorous or isovaleric anhydride, and the amorphous 6-O-(N-benzyloxycarbonylglycyl)-1, 2;3, 5-di-O-benzylidene-D-glucofuranose so obtained was converted to the crystalline 6-O, N-benzyloxycarbonylglycyl)-D-glucose. Catalytic reduction of this product finally afforded the objective 6-O-glycylglucose which was extremely labile and turned brown at room temperature to be decomposed rapidly into glucose, glycine, and glycylglycine. It was therefore impossible to obtain this compound in pure state or change it to its various derivatives, such as acetylated compound.