Synthesis of Oligosaccharide Components of the Outer Core Domain of P. aeruginosa Lipopolysaccharide Using a Multifunctional Hydroquinone-Derived Reducing-End Capping Group

Org Lett. 2018 Jan 19;20(2):353-356. doi: 10.1021/acs.orglett.7b03590. Epub 2017 Dec 29.

Abstract

The synthesis of a trisaccharide (common to glycoform I and II) and a tetrasaccharide (common to glycoform I) from the outer core domain of Pseudomonas aeruginosa lipopolysaccharide (LPS) using a novel hydroquinone-based reducing-end capping group is reported. This multifunctional capping group was utilized as purification handle and was stable toward many common transformations in oligosaccharide synthesis. The access to outer-core LPS antigens with a TBDPS-protected hydroquinone (TPH) at the reducing end will be useful for glycan array and therapeutic glycoconjugate synthesis.

Publication types

  • Research Support, N.I.H., Extramural

MeSH terms

  • Carbohydrate Sequence
  • Hydroquinones
  • Lipopolysaccharides
  • Molecular Structure
  • Oligosaccharides
  • Pseudomonas aeruginosa*

Substances

  • Hydroquinones
  • Lipopolysaccharides
  • Oligosaccharides