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Synthesis and structural characterization of the dilactone derivative of GD1a ganglioside

✍ Scribed by Giovanni Fronza; Günther Kirschner; Domenico Acquotti; Rosaria Bassi; Luigina Tagliavacca; Sandro Sonnino


Publisher
Elsevier Science
Year
1988
Tongue
English
Weight
562 KB
Volume
182
Category
Article
ISSN
0008-6215

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✦ Synopsis


Treatment of GD1a [alpha-Neu5Ac-(2----3)-beta-GalNAc-(1----4)-[alpha- Neu5Ac-(2----3)]-beta-Gal-(1----4)-beta-Glc-(1----1)-Cer] with dicyclohexylcarbodi-imide in anhydrous methyl sulfoxide affords 94-98% of GD1a-dilactone. The involvement of the carboxyl groups of the two sialic acid residues in the lactone rings was proved by ammoniolysis and reduction experiments, which gave ganglioside derivatives containing the amide of sialic acid and N-acetylneuraminulose, respectively. 1H-N.m.r. spectroscopy showed that the lactone rings involved position 2 of each galactose residue in the ester linkages.


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