Effect of anomeric linkage on the sialylation of glycosides by cells

Maria Carmelita Z. Kasuya, Maki Ikeda, Kazuhiko Hashimoto, Toshinori Sato, Kenichi Hatanaka

研究成果: Article査読

13 被引用数 (Scopus)


The synthesis of sialylated glycosides using saccharide primers and cells was investigated. α·and β·Saccharide primers were chemically synthesized and introduced into B16 melanoma cells to prime oligosaccharide synthesis. Incorporation of α- and β-dodecyl lactosides into B16 cells resulted in the sialylation of the galactose residue to give GM3-type oligosaccharides. The β-dodecyl galactoside primer was sialylated but the α-dodecyl galactoside primer was not. Both the α- and β-dodecyl glucoside primers were not elongated. In the glycosylation of primers by cells, this research confirmed that sialyl transferases tolerate acceptor modifications and are permissive to primer elongation regardless of the α- or β-linkage to the aglycon unit. However, the presence of the terminal galactose residue that is β-linked to the adjacent saccharide or aglycon unit is essential for sialylation by cellular enzymes to occur.

ジャーナルJournal of Carbohydrate Chemistry
出版ステータスPublished - 2005

ASJC Scopus subject areas

  • 生化学
  • 有機化学


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