ISSN:
1434-193X
Keywords:
Asymmetric synthesis
;
Carbohydrates
;
Pseudosugars
;
Carbohydrate mimics
;
Ganglioside GM1
;
Cholera toxin
;
Heat-labile toxin
;
Chemistry
;
General Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
-The pseudo tetrasaccharide 2 was designed to mimic ganglioside GM1, the membrane receptor of both the cholera toxin and of the heat-labile toxin of E. coli. Compound 2 retains the Gal and Neu5Ac recognition determinant of GM1 and uses as the scaffold element a new, conformationally restricted cyclohexanediol (DCCHD 3), with the same relative and absolute configuration of natural galactose. The diol 3 was enantioselectively synthesized by an asymmetric Diels-Alder reaction, followed by dihydroxylation of the resulting cyclohexene. Glycosylation of 3 with the sialyl donor 17 and the Galβ(1-3)GalNAc donor 15, followed by removal of the protecting groups, completed the synthesis of 2.
Additional Material:
1 Ill.
Type of Medium:
Electronic Resource
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