A Total Synthesis of the Methyl Glycoside of Ganglioside GM1
- 12 December 1999
- journal article
- research article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 65 (1) , 144-151
- https://doi.org/10.1021/jo9912496
Abstract
The total synthesis of the methyl glycoside of GM1 (1b) has been accomplished. The key step in the synthesis involves the sulfonamidoglycosidation reaction, which is used to create a β-linkage leading to a GalNAc residue joined to the C4 hydroxyl group of a galactose unit of a C3 sialylated lactosyl moiety. The “proximal hydroxyl” directing effect, which has been postulated before, manifests in this context as well leading to the preponderant formation of the β-glycoside. Together with asialo GM1 and other substructures, the GM1 methyl glycoside has been submitted for biological assays as potential ligands for bacterial and viral infection sites.Keywords
This publication has 13 references indexed in Scilit:
- Synthesis of Asialo GM1. New Insights in the Application of Sulfonamidoglycosylation in Oligosaccharide Assembly: Subtle Proximity Effects in the Stereochemical Governance of GlycosidationJournal of the American Chemical Society, 1998
- Glycals in Organic Synthesis: The Evolution of Comprehensive Strategies for the Assembly of Oligosaccharides and Glycoconjugates of Biological ConsequenceAngewandte Chemie International Edition in English, 1996
- Glycosyl imidates, 73. Synthesis of ganglioside gm1 via a GA1 intermediateEuropean Journal of Organic Chemistry, 1995
- Cystic fibrosis epithelial cells have a receptor for pathogenic bacteria on their apical surface.Proceedings of the National Academy of Sciences, 1995
- Receptor specificity of adherence of Streptococcus pneumoniae to human type-II pneumocytes and vascular endothelial cells in vitroMicrobial Pathogenesis, 1994
- A facile, systematic synthesis of ganglio-series gangliosides: Total synthesis of gangliosides GM1 and GD1aCarbohydrate Research, 1992
- Defective acidification of intracellular organelles in cystic fibrosisNature, 1991
- Many pulmonary pathogenic bacteria bind specifically to the carbohydrate sequence GalNAc beta 1-4Gal found in some glycolipids.Proceedings of the National Academy of Sciences, 1988
- Total synthesis of gangliosides GM1 and GM2Carbohydrate Research, 1986
- Synthesis of a hematoside (GM3-ganglioside) and a stereoisomerGlycoconjugate Journal, 1985