グルクロン酸とグルコースとのα (1,4) 重合体に関する研究 (第1報)

Benzyl Maltosideの接触酸化による4-O-(α-D-Glucopyranosiduronyl)-D-glucoseの合成

抄録

There are two kinds of chief products by thorough catalytic oxidation of benzyl maltoside (I) and they were confirmed to be benzyl 4-O-(α-D-glucopyranosiduronyl)-D-glucoside (II) and benzyl glucuronoside (III). II was isolated as the crystalline methyl ester hexaacetate (IV) by the acetylation of a mixture of oxidation products. All the protective groups in III were liberated and purified by cellulose adsorption to glucuronic acid (VIII). The structure of II was determined from the analyses of IV, of 4-O-(α-D-glucopyranosiduronyl)-D-glucose prepared from VI, and of two kinds of methylated sugar obtained by methylation of VI followed by acid hydrolysis. VIII was confirmed by its derivation to crystalline glucuronolactone (XI). Contrary to expectations, presence of benzyl 4-O-(α-D-glucopyranosiduronyl)-D-glucuronoside (XII) was not detected in the oxidation product.
Further catalytic oxidation of II merely gave III, with recovery of II and formation of XII was not detected. Oxidation of II, therefore, seems to cause severance of the α (1, 4) linkage. Various properties of the new compound (VI), especially the result of its acid hydrolysis, are discussed.