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
Synthesis, structure, and conformation of the dilactone derivative of Gd1b ganglioside
β Scribed by Giovanni Fronza; Gunther Kirschner; Domenico Acquotti; Sandro Sonnino
- Publisher
- Elsevier Science
- Year
- 1989
- Tongue
- English
- Weight
- 575 KB
- Volume
- 195
- Category
- Article
- ISSN
- 0008-6215
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β¦ Synopsis
Treatment of DG1b, beta-Gal-(1----3)-beta-GalNAc-(1---- 4)-[alpha-Neu5Ac-(2----8)-alpha-Neu5Ac-(2---- 3)]-beta-Gal-(1----4)-beta-Glc-(1----1)-Cer, with dicyclohexylcarbodi-imide in anhydrous methyl sulfoxide affords 95-98% of GD1b-dilactone. The carboxyl groups of the two sialic acid units are involved in ester linkages, as proved by ammoniolysis and reduction which gave derivatives containing the amide of sialic acid and N-acetylneuraminulose, respectively. 1H-N.m.r. spectroscopy showed that the lactone rings involved position 9 of the inner sialic acid and position 2 of the inner galactose and that the disialosyl chain is extended toward the -beta-Gal-(1 ----4)-beta-Glc- portion of the ganglioside moiety.
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Mammals, birds, amphibians, and teleost fish all have similar brain gangliosides. These gangliosides are of the ganglio-series with predominantly, gangliotetraose, P-o-Gal-(1 + 3)-fl-D-GalNAc-(1 + +&o-Gal-( 1+ 4)-~-Gk, as the neutral oligosaccharide, though with a varying degree of sialylation. Sinc
## Abstract A small number of macrocyclic dilactones of type **3**, __i.e.__, **9, 10, 11**, and epiβ**11**, comprising a 3,4βdihydroxypentanoic acid unit, the pharmacophore of aplysiatoxin, and a conformationally preorganized __Ο__βhydroxynonanoic acid unit were synthesized. Conformational analysi
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