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

13 引用 (Scopus)

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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.

元の言語English
ページ(範囲)705-715
ページ数11
ジャーナルJournal of Carbohydrate Chemistry
24
発行部数7
DOI
出版物ステータスPublished - 2005 11 28

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ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry

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