期刊
CHEMISTRY-A EUROPEAN JOURNAL
卷 14, 期 23, 页码 7072-7081出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.200800757
关键词
carbohydrates; glycosylation; N-glycans; synthesis design
资金
- National Institute of General Medical Sciences [R01-GN172667]
- National Science Foundation [CHE 0547504]
- NATIONAL INSTITUTE OF GENERAL MEDICAL SCIENCES [R01GM072667] Funding Source: NIH RePORTER
Synthesis of N-glycans is of high current interests due to their important biological properties. A highly efficient convergent strategy based oil the pre-activation method for assembly of the complex type core fucosylated bi-antennary N-glycan dodecasaccharide has been developed. Retrosynthetically this extremely challenging target is broken down to three modules: a sialyl disaccharide, a glucosamine building block and a hexasaccharide diol acceptor. The sialyl disaccharide was easily obtained by selective activation of a new 5-N-trichloroacetyl protected sialyl donor in the presence of a thiogalactoside acceptor. The hexasaccharide diol module was produced by double mannosylation of a fucosylated tetrasaccharide acceptor, which in turn was generated by glycosylation of a fucosylated disaccharide with a beta-mannose containing disaccharide donor. The union of the three modules was performed in one-pot giving the fully protected dodecasaccharide in high yield. This synthesis is characterized by minimum protective group and aglycon adjustment on oligosaccharide intermediates, thus greatly enhancing the overall synthetic efficiency. The modular feature of this strategy Suggests that this method can be readily adapted to the synthesis of a wide variety of N-glycan structures.
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