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Glycosphingolipid


DATA No : GSG3035 INFORMANT : Hideharu Ishida

NAME : N-acetylneuraminyla2-3galactosylb1-3(N-acetylneuraminyla2-6)N-acetyl- -galactosaminylb1-4(N-acetylneraminyla2-8N-acetylneraminyla2-3)galactosylb1-4glucosylceramide

COMMON NAME:
SYMBOL: GQ1ba
FORMULA: C106H182N6O55 MOL.WT (average) : 2420.587


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BIOLOGICAL ACTIVITY
This ganglioside is the most potent neuronal ligands for myelin-associated glycoprotein. (Ref. 3040)
Binding specificites of the sialoadhesin family of I-type lectins was examined by employing this ganglioside. (Ref. 3046)
PHYSICAL AND CHEMICAL PROPERTIES
MELTING POINT:

BOILING POINT:

REFRACTIVE INDEX:

OPTICAL ROTATION:-13.0deg(Ref. 3023)

DENSITY:

SOLUBILITY:
SPECTRAL DATA
UV SPECTRA:

IR SPECTRA:

NMR SPECTRA:1D 1H-NMR (Ref. 3023)

MASS SPECTRA:

OTHER SPECTRA:
CHROMATOGRAM DATA

SOURCE
Chemical Synthesis
CHEMICAL SYNTHESIS
Regio- and stereo-selective monosialylation of C-6 of N-acetylgalactosamine residue and the subsequent disialylation with methyl (phenyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-2-thio-D-glycero-D-galacto-2-nonulopyranosid)onate of C-3 of galactose residue with methyl [phenyl 5-acetamido-8-O-(5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-a-D-galacto-2-nonulopyranosylono-1',9-lactone)-4,7-di-O-acetyl-3,5-dideoxy-2-thio-D-glycero-D-galacto-2-nonulopyranosid]onateon 2-(trimethylsilyl)ethyl O-(2-acetamido-2-deoxy-3,4-O-isopropylidene-b-D-galactopyranosyl)-(1-4)-O-(2,6-di-O-benzyl-b-D-galactopyranosyl)-(1-4)-O-2,3,6-tri-O-benzyl-b-D-glucopyranoside by use of N-iodosuccinimide (NIS)-trifluoromethanesulfonic acid (TfOH) as a promoter gave the corresponding hexasaccharide, containing a-glycosidicaly-linked monomeric sialic acid at
C-6 of N-acetylgalactosamine residue and dimeric sialic acid at C-3 of galactose residue on gangliotriose moiety, which was transformed into the acceptor by removal of isopropylidene group. Condensation of methyl O-(methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-a-D-galacto-2-nonulopyranosylonate)-(2-3)-2,4,6-tri-O-benzoyl-1-thio-b-D-galactopyranoside with the hexasaccharide acceptor, using dimethyl(methylthio)sulfonium triflate (DMTST) as a promoter, gave the desired octasaccharide derivative in high yield. The introduction of the ceramide moiety into the octasaccharide, O-deacylation, and hydrolysis of the methyl ester group gave the title ganglioside in good yield. (Ref. 3023)
METABOLISM

GENETIC INFORMATION

NOTE
Fatty acid C18:0

LCB d18:1
REFERENCES
[3023]
AUTHOR:Hotta, K., Ishida, H., Kiso, M., and Hasegawa, A.
TITLE:First total synthesis of a cholinergic neuron-specific ganglioside GQ1ba.
JOURNAL:Journal of Carbohydrate Chemistry
VOL:1445 PAGE : 491 -506 (1995)
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[3040]
AUTHOR:Yang, L. J., Zeller, C. B., Shaper, N. L., Kiso, M., Hasegawa, A., Shapiro, R. E., and Schnaar, R. L.
TITLE:Gangliosides are neuronal ligands for myelin-associated glycoprotein PubMed ID:8570640
JOURNAL:Proc Natl Acad Sci U S A.
VOL:93 PAGE : 814-818 (1996)
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[3046]
AUTHOR:Collins, B. E., Kiso, M., Hasegawa, A., Tropak, M. B., Roder, J. C., Crocker, P. R., and Schnaar, R. L.
TITLE:Binding specificities of the sialoadhesin family of I-type lectins. Sialic acid linkage and substructure requirements for binding of myelin-associated glycoprotein, Schwann cell myelin protein, and sialoadhesin PubMed ID:9201997
JOURNAL:J Biol Chem.
VOL:272 PAGE : 16889-16895 (1997)
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Last updated June 19, 2007. Copyright © 1989-2007 Japanese Conference on the Biochemistry of Lipids (JCBL). All rights reserved.