Synthesis of multiantennary complex type N-glycans by use of modular building blocks

Chemistry. 2009 Nov 16;15(45):12292-302. doi: 10.1002/chem.200901908.

Abstract

A modular set of oligosaccharide building blocks was developed for the synthesis of multiantennary N-glycans of the complex type, which are commonly found on glycoproteins. The donor building blocks were laid out for the elongation of a core trisaccharide acceptor (beta-mannosyl chitobiose) conveniently protected with a single benzylidene moiety at the beta-mannoside. Through two consecutive regio- and stereoselective couplings the donors gave N-glycans with three to five antennae in high yields. Due to the consistent protection group pattern of the donors the deprotection of the final products can be performed by using a general reaction sequence.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Carbohydrate Conformation
  • Disaccharides / chemical synthesis
  • Disaccharides / chemistry
  • Glycoproteins / chemical synthesis
  • Glycoproteins / chemistry
  • Mannosides / chemical synthesis
  • Mannosides / chemistry
  • Molecular Structure
  • Oligosaccharides / chemical synthesis
  • Oligosaccharides / chemistry
  • Polysaccharides / chemical synthesis*
  • Polysaccharides / chemistry

Substances

  • Disaccharides
  • Glycoproteins
  • Mannosides
  • Oligosaccharides
  • Polysaccharides
  • chitobiose