Synthesis of a novel glycosphingolipid from the millipede, Parafontaria laminata armigera, and the assembly of its carbohydrate moiety into multivalent structures

Noriyasu Hada, Yoshiko Sonoda, Tadahiro Takeda

Research output: Contribution to journalArticle

18 Citations (Scopus)

Abstract

A novel glycosphingolipid, β-d-Manp-(1→4)-[α-l-Fucp-(1→3)]-β-d-Glcp-(1→1)-Cer, found in the millipede, Parafontaria laminata armigera, and multivalent derivatives of its carbohydrate moiety were synthesized. As the key step, the target glycolipid (1) was obtained through an inversion reaction at the 2-position of a β-glucopyranoside residue yielding a β-mannopyranoside. In addition, the synthesis of fluorescently labeled trimer and tetramer glycoconjugates (2, 3) was achieved by iterative amide bond formation using a monomer unit (24).

Original languageEnglish
Pages (from-to)1341-1352
Number of pages12
JournalCarbohydrate Research
Volume341
Issue number10
DOIs
Publication statusPublished - 2006 Jul 24

Keywords

  • Glycocluster
  • Glycosphingolipids
  • Intermolecular nucleophile approach
  • Parafontaria laminata armigera

ASJC Scopus subject areas

  • Analytical Chemistry
  • Biochemistry
  • Organic Chemistry

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