Synthesis of a core trisaccharide as a versatile building block for N-glycans and glycoconjugates.
N-linked oligosaccharides from glycoproteins (N-glycans) can be conveniently assembled with a building block approach. A protected form of the core trisaccharide (beta-mannosyl chitobiose) was identified as a key building block. The chitobiose part of the core trisaccharide was built from a glycosyl fluoride, which served as a precursor for the reducing GlcNAc azide and the inner GlcNAc moiety. Beta-mannosylation was accomplished at the trisaccharide stage by intramolecular inversion of a beta-glucosyl chitobiose. The benzylidene protection of the beta-mannoside and the azido group at the reducing end of the core trisaccharide allow modular synthesis of N-glycans and their glycoconjugates.
Unverzagt
Carlo
C
Institut für Organische Chemie und Biochemie, Technische Universität München, Lichtenbergstrasse 4, 85748 Garching, Germany. Carlo.Unverzagt@uni-bayreuth.de
D002236:Carbohydrate Conformation; D002240:Carbohydrate Sequence; D006001:Glycoconjugates / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D008969:Molecular Sequence Data; D011134:Polysaccharides / Q000737:chemistry*; D014312:Trisaccharides / Q000737:chemistry*
D006001:Glycoconjugates; D011134:Polysaccharides; D014312:Trisaccharides