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Synthesis of a Pseudo Tetrasaccharide Mimic of Ganglioside GM1

✍ Scribed by Anna Bernardi; Giovanna Boschin; Anna Checchia; Maria Lattanzio; Leonardo Manzoni; Donatella Potenza; Carlo Scolastico

Publisher: John Wiley and Sons
Year: 1999
Tongue: English
Weight: 305 KB
Volume: 1999
Category: Article
ISSN: 1434-193X
DOI: 10.1002/(sici)1099-0690(199906)1999:6<1311::aid-ejoc1311>3.0.co;2-w

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✦ Synopsis

The pseudo tetrasaccharide 2 was designed to mimic diol 3 was enantioselectively synthesized by an asymmetric Diels-Alder reaction, followed by dihydroxylation of the ganglioside GM1, the membrane receptor of both the cholera toxin and of the heat-labile toxin of E. coli. Compound 2 resulting cyclohexene. Glycosylation of 3 with the sialyl donor 17 and the Galβ(1-3)GalNAc donor 15, followed by retains the Gal and Neu5Ac recognition determinant of GM1 and uses as the scaffold element a new, conformationally removal of the protecting groups, completed the synthesis of 2. restricted cyclohexanediol (DCCHD 3), with the same relative and absolute configuration of natural galactose. The nants Gal and Neu5Ac of 2 in the appropriate position for [a] Dipartimento di Chimica Organica e Industriale, and Centro tion of the axial hydroxy group with an appropriate donor CNR Sostanze Organiche Naturali, of Galβ(1-3)GalNAc, followed by sialylation of 4 (see via Venezian 21

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