25 糖アミノ酸残基を基盤とした新規糖類縁体の合成と生理活性物質への応用(口頭発表の部)

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Carbohydrates and peptides play key roles in a variety of disease-related processes; however, use of naturally occurring carbohydrates and peptides as chemotherapeutic agents has often been hampered by their susceptibility to digestion by glycosidases and proteases. There has been a considerable interest in designing and constructing mimetics of the oligosaccharide and peptide molecules with the expectation that these molecules may provide stable alternatives to the biologically important natural carbohydrates and peptides. Glycamino acids, are a unique class of carbohydrate-based molecules that possess both a carboxylate group at the anomeric position and an amino group replacing one of the OH groups of the carbohydrate. As a part of our ongoing program to develop a new class of molecules that possess the structural and functional features of both carbohydrates and peptides, we have synthesized the first homooligomers of glycamino acids in which the glycamino acid residues are connected via β(1→2)-, 13(1→3)-,β(1→4)-, and β(1→6)-linkages, and hybrid molecules composed of a repeating unit of glycamino acid and aspartic acid. We found that, upon O-sulfation, the amido-linked oligosaccharide analogs were able to inhibit the replication of HIV-1, sialyl Lewis x-dependent cell adhesion and heparanase activity.
天然有機化合物討論会の論文
1999-09-01