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 |