Glycosphingolipid

DATA No : GSG3037 INFORMANT : Hideharu Ishida

NAME : N-acetylneraminyla2-3galactosylb1-3-N-acetyl-galactosaminyl-b1-3galactosyl-a1-4galactosylb1-4glucosylceramide

COMMON NAME	:	SSEA-4
SYMBOL	:
FORMULA	:	C₇₉H₁₄₁N₃O₃₇ MOL.WT (average) : 1724.963

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BIOLOGICAL ACTIVITY

PHYSICAL AND CHEMICAL PROPERTIES

MELTING POINT	:

BOILING POINT	:

REFRACTIVE INDEX	:

OPTICAL ROTATION	:	-3.0(Ref. 3025)

DENSITY	:

SOLUBILITY	:

SPECTRAL DATA

UV SPECTRA	:

IR SPECTRA	:

NMR SPECTRA	:	1D 1H-NMR (Ref. 3025)

MASS SPECTRA	:

OTHER SPECTRA	:

CHROMATOGRAM DATA

SOURCE

Chemical Synthesis

CHEMICAL SYNTHESIS

a-Selective 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 galactose donor, methyl 3-O-acetyl-2-O-benzyl-4,6-O-benzylidene-1-thio-b-D-galactopyranoside gave the desired trisaccharide, which was transformed into the trisaccharide acceptor, by removal of the O-acetyl group. Glycosylation of this acceptor with methyl 3-O-acetyl-4,6-O-benzylidene-2-deoxy-2-phthalimido-1-thio-b-D-galactopyranoside gave the globotetraose derivative, which was transformed into the acceptor by removal of the phthaloyl and O-acetyl groups followed by N-acetylation.
DMTST promoted coupling of this acceptor with 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-ben-zoyl-1-thio-b-D-galactopyranoside afforded the desired sialyl globopentaoside derivative in good yield, which was transformed, by removal of the benzyl and benzylidene groups followed by O-acetylation, selective removal of the 2-(trimethylsilyl)ethyl group and subsequent imidate formation, into the final glycosyl donor. Condensation of this imidate derivative with (2S,3R,4E)-2-azido-3-O-benzoyl-4-octadecene-1,3-diol gave the b-glycoside, which on channeling through selective reduction of the azido group, coupling of the amino group with octadecanoic acid, O-deacylation and saponification of the methyl ester group, gave the title compound, sialyl globopentaosyl ceramide.(Ref. 3025)

METABOLISM

GENETIC INFORMATION

NOTE

Fatty acid C18:0

LCB d18:1

REFERENCES

[3025]

AUTHOR	:	Ishida, H., Miyawaki, R., Kiso, M., and Hasegawa, A.
TITLE	:	First total synthesis of sialyl globopentaosyl ceramide (V3Neu5AcGb5Cer) and its positional isomer (V6Neu5AcGb5Cer).
JOURNAL	:	Journal of Carbohydrate Chemistry
VOL	:	152 PAGE : 163 -185 (1996)

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