Advances in the Chemical Synthesis of Carbohydrates and Glycoconjugates

Adv Biochem Eng Biotechnol. 2021:175:201-230. doi: 10.1007/10_2020_150.

Abstract

Carbohydrates are functional and structural biomolecules with structures ranging from monosaccharides to polysaccharides. They are naturally found as pure glycans or attached to lipids and proteins forming glycoconjugates. The biosynthesis of carbohydrates is not genetically controlled. The regulation takes place by the expression of enzymes that transfer and hydrolyze the glycan units, leading to glycocojugates having complex mixtures of glycan structures. Chemical synthesis emerged as the best strategy to obtain defined glycan and glycoconjugates and overcome the challenging purification processes. Here, we review the recent advances in the synthesis of oligosaccharides using manual and automated methods. The chapter covers the methods for the preparation of building blocks and control of stereoselectivity and regioselectivity during glycosylations. Finally, it also presents the strategies to obtain natural and non-natural glycoconjugates with lipids and proteins.

Keywords: Carbohydrates; Chemical synthesis; Glycan modifications; Glycoconjugates; Glycoproteins.

Publication types

  • Review

MeSH terms

  • Carbohydrate Sequence
  • Carbohydrates*
  • Glycoconjugates*
  • Oligosaccharides
  • Polysaccharides

Substances

  • Carbohydrates
  • Glycoconjugates
  • Oligosaccharides
  • Polysaccharides