ISSN:
1434-193X
Schlagwort(e):
Asymmetric synthesis
;
Carbohydrates
;
Pseudosugars
;
Carbohydrate mimics
;
Ganglioside GM1
;
Cholera toxin
;
Heat-labile toxin
;
Chemistry
;
General Chemistry
Quelle:
Wiley InterScience Backfile Collection 1832-2000
Thema:
Chemie und Pharmazie
Notizen:
-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.
Zusätzliches Material:
1 Ill.
Materialart:
Digitale Medien
Permalink
