A versatile strategy for the synthesis of complex type N-Glycans: Synthesis of diantennary and bisected diantennary oligosaccharides
1998; Elsevier BV; Volume: 39; Issue: 16 Linguagem: Inglês
10.1016/s0040-4039(98)00246-9
ISSN1873-3581
AutoresSven Weiler, Richard R. Schmidt,
Tópico(s)Proteoglycans and glycosaminoglycans research
ResumoBased on readily available glucose, 2-azido-glucose, mannose, and N-phthaloyllactosamine building blocks 5, 6, 8, and 13 a highly versatile strategy for the synthesis of complex type and bisected complex type N-glycan residues is established; this is demonstrated for the synthesis of nonasaccharide 1 and decasaccharide 2, respectively. The glucose residue 5 finally provides regioselective access to the 3-, 4-, and/or 6-hydroxy groups for antenna attachment, introduction of the bisecting N-acetylglucosamine residue, and epimerisation at C-2 in order to generate the required β-linked mannosyl residue c.
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