Chemical Synthesis of Rare, Deoxy-Amino Sugars Containing Bacterial Glycoconjugates as Potential Vaccine Candidates

Molecules. 2018 Aug 10;23(8):1997. doi: 10.3390/molecules23081997.

Abstract

Bacteria often contain rare deoxy amino sugars which are absent in the host cells. This structural difference can be harnessed for the development of vaccines. Over the last fifteen years, remarkable progress has been made toward the development of novel and efficient protocols for obtaining the rare sugar building blocks and their stereoselective assembly to construct conjugation ready bacterial glycans. In this review, we discuss the total synthesis of a variety of rare sugar containing bacterial glycoconjugates which are potential vaccine candidates.

Keywords: bacterial glycoconjugates; rare deoxy-amino sugars; stereoselective glycosylation; total synthesis; vaccine candidates; zwitterionic polysaccharides.

Publication types

  • Review

MeSH terms

  • Amino Sugars / chemistry*
  • Animals
  • Antigens, Bacterial / chemistry*
  • Antigens, Bacterial / immunology*
  • Bacteria / chemistry*
  • Bacteria / classification
  • Bacteria / immunology*
  • Bacterial Infections / prevention & control
  • Bacterial Vaccines / chemical synthesis
  • Bacterial Vaccines / chemistry
  • Bacterial Vaccines / immunology*
  • Glycoconjugates / chemical synthesis
  • Glycoconjugates / chemistry*
  • Glycoconjugates / immunology*
  • Glycosylation
  • Humans
  • Polysaccharides / chemistry
  • Polysaccharides, Bacterial / chemical synthesis
  • Polysaccharides, Bacterial / chemistry
  • Polysaccharides, Bacterial / immunology
  • Serogroup

Substances

  • Amino Sugars
  • Antigens, Bacterial
  • Bacterial Vaccines
  • Glycoconjugates
  • Polysaccharides
  • Polysaccharides, Bacterial