A total synthesis of the methyl glycoside of ganglioside GM1 Journal Article


Authors: Bhattacharya, S. K.; Danishefsky, S. J.
Article Title: A total synthesis of the methyl glycoside of ganglioside GM1
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: nonhuman; molecular sequence data; antigen recognition; magnetic resonance spectroscopy; virus infection; ganglioside gm1; bacterial infection; carbohydrate analysis; carbohydrate sequence; glycosides; carbohydrate conformation; g(m1) ganglioside; article; phospholipid synthesis; spectrometry, mass, fast atom bombardment
Journal Title: Journal of Organic Chemistry
Volume: 65
Issue: 1
ISSN: 0022-3263
Publisher: American Chemical Society  
Date Published: 2000-01-14
Start Page: 144
End Page: 151
Language: English
DOI: 10.1021/jo9912496
PUBMED: 10813908
PROVIDER: scopus
DOI/URL:
Notes: Export Date: 18 November 2015 -- Source: Scopus
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