Synthesis of a common tetrasaccharide motif of Haemophilus influenzae LPS inner core structures

Org Biomol Chem. 2008 Mar 21;6(6):1087-91. doi: 10.1039/b717564g. Epub 2008 Feb 14.

Abstract

A conserved tetrasaccharide structure, L-glycero-alpha-D-manno-heptopyranosyl-(1-->2)-(6-O-aminoethylphosphono-L-glycero-alpha-D-manno-heptopyranosyl)-(1-->3)-[beta-D-glucopyranosyl-(1-->4)]-L-glycero-alpha-D-manno-heptopyranose, from the LPS inner core of Haemophilus influenzae has been synthesised as its ethylamino glycosides to allow later conjugations. Starting from a previously synthesised suitably protected trisaccharide intermediate, the third heptose and subsequently the spacer were introduced using thioglycoside donor chemistry. The phosphoethanolamine was formed employing a Boc-protected phosphoamidite. Final deprotection and conjugation to biotin gave conjugates that will be used to study the specificity of MAbs raised against native LPS structures.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Biotin / chemistry
  • Carbohydrate Conformation
  • Carbohydrate Sequence
  • Haemophilus influenzae / chemistry*
  • Lipopolysaccharides / chemistry*
  • Molecular Sequence Data
  • Oligosaccharides / chemical synthesis*
  • Oligosaccharides / chemistry

Substances

  • Lipopolysaccharides
  • Oligosaccharides
  • Biotin