Glycosphingolipid

DATA No : GSG3021 INFORMANT : Hideharu Ishida

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

COMMON NAME	:
SYMBOL	:	GM1a
FORMULA	:	C₇₃H₁₃₁N₃O₃₂ MOL.WT (average) : 1562.822

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BIOLOGICAL ACTIVITY

This gangliosideis is not recognized by 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	:	+5.4(Ref. 3014)

DENSITY	:

SOLUBILITY	:

SPECTRAL DATA

UV SPECTRA	:

IR SPECTRA	:

NMR SPECTRA	:	1D 1H-NMR (Ref. 3014)

MASS SPECTRA	:

OTHER SPECTRA	:

CHROMATOGRAM DATA

SOURCE

Chemical Synthesis

CHEMICAL SYNTHESIS

Glycosylation of 2-(trimethylsilyl)ethyl O-(2,3,6-tri-O-benzyl-b-D-galactopyranosyl)-(1-4)-2,3,6-tri-O-benzyl-b-D-glucopyranoside with the suitably protected galactosamine donor, methyl 3-O-acetyl-4,6-O-benzylidene-2-deoxy-2-phthalimido-1-thio-b-D-galactopyranoside gave the desired trisaccharide, which was transformed into the trisaccharide acceptor via removal of the phthaloyl and o-acetyl groups followed by N-acetylation. Glycosylation of this acceptor with methyl 3-O-benzyl-2,4,6-tri-O-benzoyl-1-thio-b-D-galactopyranoside gave the asialo GM1 saccharide derivative, which was transformed into the acceptor by removal of benzylidene group.
Coupling of this gangliotetraose acceptor with phenyl (methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-2-thio-D-glycero-D-galacto

METABOLISM

GENETIC INFORMATION

NOTE

Fatty acid C18:0

LCB d18:1

REFERENCES

[3014]

AUTHOR	:	Hotta, K., Komba, S., Ishida, H., Kiso, M., and Hasegawa, A.
TITLE	:	Synthesis of a-series ganglioside GM1a.
JOURNAL	:	Journal of Carbohydrate Chemistry
VOL	:	135 PAGE : 665 -677 (1994)

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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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