C-Sialosides: Synthesis and biological activities

Go Hirai, Eisuke Ota, Motonari Sakai, Shigeru Nishiyama, Mikiko Sodeoka

Research output: Contribution to journalReview article

Abstract

This mini-review focuses on the synthesis and biological activities of sialic acid (SA) derivatives with a C-glycosidic linkage in place of the standard O-glycosidic bond at the C-2 position. We summarize reported synthetic methodologies for monoand di-saccharides in separate sections. Then, we introduce our strategy for the construction of C-sialoside linkages utilizing Ireland-Claisen rearrangement reaction and its application to the synthesis of a ganglioside GM4 analogue. Although C-sialosides are expected to be useful as sialidase-resistant analogues of sialoglycoconjugates (sialoGCs), their biological activities have not yet been investigated in detail. Herein we briefly discuss the potential applications of C-sialosides.

Original languageEnglish
Pages (from-to)47-60
Number of pages14
JournalTrends in Glycoscience and Glycotechnology
Volume27
Issue number154
DOIs
Publication statusPublished - 2015 Jan 1
Externally publishedYes

Keywords

  • C-glycosides
  • Gangliosides
  • Influenza infection
  • Ireland-Claisen rearrangement reaction
  • Organic synthesis
  • Radical coupling
  • Sialic acid
  • Sialidase
  • Sialoglycoconjugate
  • SmI2-mediated coupling reaction

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry

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