Assembly of a series of malarial glycosylphosphatidylinositol anchor oligosaccharides

Yong Uk Kwon, Regina L. Soucy, Daniel A. Snyder, Peter H. Seeberger

Research output: Contribution to journalArticlepeer-review

50 Scopus citations

Abstract

We report an efficient and convergent synthesis of a series of oligosaccharides comprised of the malaria GPI glycan (2 a), a promising anti-malaria vaccine candidate currently in preclinical trials and several related oligosaccharide sequences (3-8) that are possible biosynthetic precursors of the malarial GPI. A flexible synthetic strategy is disclosed that relies on a late-stage coupling between oligomanno sides of varying length and pseudodis-accharide glycosyl acceptor 11 to readily access various malarial GPI structures. Phosphorylation was accomplished by mild and efficient H-phosphonate chemistry before the final deprotection was carried out by using sodium in ammonia. The direct connection of a thiol group via a phosphate diester linkage to the inositol moiety provides a handle for easy conjugation of the GPI glycan to carrier proteins, immobilization on carbohydrate micro-arrays and photo-affinity labels identification. These synthetic oligosaccharides will serve as molecular probes.

Original languageEnglish
Pages (from-to)2493-2504
Number of pages12
JournalChemistry - A European Journal
Volume11
Issue number8
DOIs
StatePublished - 8 Apr 2005

Keywords

  • Carbohydrates
  • Glycosylation
  • Malaria
  • Oligosaccharides
  • Vaccines

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