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Glycosphingolipid


DATA No : GSG3003 INFORMANT : Hideharu Ishida

NAME : N-acetylneraminyla2-3galactosylb1-4glucosylceramide

COMMON NAME:
SYMBOL: GM3
FORMULA: C65H120N2O21 MOL.WT (average) : 1265.649


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BIOLOGICAL ACTIVITY
This ganglioside have the immunosuppressive properties of the natural molecules and are useful in probing which elements of ganglioside structure are critical to their biological activity.(Ref. 3002)
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:+0.8deg(Ref. 3001)

DENSITY:

SOLUBILITY:
SPECTRAL DATA
UV SPECTRA:

IR SPECTRA:(Ref. 3001)

NMR SPECTRA:1D 1H-NMR (Ref. 3001)

MASS SPECTRA:

OTHER SPECTRA:
CHROMATOGRAM DATA

SOURCE
Chemical Synthesis
CHEMICAL SYNTHESIS
Coupling of a-(trimethylsilyl)ethyl O-(6-O-benzoyl-b-D-galactopyranosyl)-(1-4)-2,6-di-O-benzoyl-b-D-glucopyranoside, prepared from 2-(trimethylsilyl)ethyl b-lactoside by selective 3'-O-benzylation, O-bezoylation, and subsequent removal of the benzyl group, with methyl(methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-2-thio-D-glycero-a-D-galacto-2-nonulopyranosid)onate using dimethyl(methylthio)sulfonium triflate as a glycosyl promoterm gave 2-(trimethylsilyl)ethyl O-(methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-a-D-galacto-2-nonulopyranosylonate)-(2-3)-O-(6-O-benzoyl-b-D-galactopyranosyl)-(1-4)-2,6-di-O-benzoyl-b-D-glucopyranoside, which was converted,
via O-acetylation, selective removal of the 2-(trimethylsilyl)ethyl group, and subsequent imidate formation, into the a-N-acetylneuraminyl-(2-3')-lactose trichloroacetimidate. Glycosylation of (2S,3R,4E)-2-azido-3-O-benzoyl-4-octadecene-1,3-diol with afforded the b-glycoside, which was converted, via selective of the azide group, coupling with tetracosanoic acid, O-deacylation, and de-esterification, into the title compounds. (Ref. 3001)
METABOLISM

GENETIC INFORMATION

NOTE
Fatty acid C24:0

LCB d18:1
REFERENCES
[3001]
AUTHOR:Murase, T., Ishida, H., Kiso, M., and Hasegawa, A.
TITLE:A facile, regio- and stereo-selective synthesis of ganglioside GM3 PubMed ID:2776130
JOURNAL:Carbohydr Res.
VOL:188 PAGE : 71-80 (1989)
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[3002]
AUTHOR:Ladisch, S., Hasegawa, A., Li, R., and Kiso, M.
TITLE:Immunosuppressive activity of chemically synthesized gangliosides PubMed ID:7827069
JOURNAL:Biochemistry.
VOL:34 PAGE : 1197-1202 (1995)
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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.