Effect of anomeric linkage on the sialylation of glycosides by cells

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

Research output: Contribution to journalArticle

13 Citations (Scopus)

Abstract

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.

Original languageEnglish
Pages (from-to)705-715
Number of pages11
JournalJournal of Carbohydrate Chemistry
Volume24
Issue number7
DOIs
Publication statusPublished - 2005 Nov 28

Keywords

  • Ganglioside
  • Glycoside primer
  • Oligosaccharide
  • Sialylation
  • α,β Anomer

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry

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