3β-Hydroxysialic Acid Glycosides. I. Calcium-Binding Ability and Chemical and Enzymatic Stabilities

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Methyl α- and β-glycosides of N-acetylneuraminic acid (Neu5Ac) and N-acetyl-3β-hydroxyneuraminic acid (Neu5Acβ3OH) (1-4) were prepared to evaluate their calcium-binding ability. (Methyl α-glucopyranosidonyl) α- and β-, and 4-methylumbelliferyl α-glycosides of Neu5Ac and Neu5Acβ3OH (5-10) were also synthesized for the comparison of chemical and enzymatic stabilities, respectively. Methyl β-glycosides of Neu5Ac and Neu5Acβ3OH, 3 and 4,respectively, showed intense calcium-binding abilities, while no such ability was observed in the corresponding α-glycosides, 1 and 2. The Neu5Aβ3OH glycosides, 6,8,and 10,showed much stronger resistance to acidic hydrolysis and sialidase digestion than the corresponding Neu5Ac glycosides, 5,7,and 9.
公益社団法人日本薬学会の論文
1992-10-25