Glycosphingolipid

DATA No : GSG3048 INFORMANT : Hideharu Ishida

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

COMMON NAME	:
SYMBOL	:	GT1aa
FORMULA	:	C₉₅H₁₆₅N₅O₄₈ MOL.WT (average) : 2145.331

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BIOLOGICAL ACTIVITY

PHYSICAL AND CHEMICAL PROPERTIES

MELTING POINT	:

BOILING POINT	:

REFRACTIVE INDEX	:

OPTICAL ROTATION	:	+2.0

DENSITY	:

SOLUBILITY	:

SPECTRAL DATA

UV SPECTRA	:

IR SPECTRA	:

NMR SPECTRA	:	1D 1H-NMR (Ref. 3031)

MASS SPECTRA	:	FAB MS (negative ion mode, triethanolamine matrix): 2172.04 [M-Na]^-, 2150.06, 2149.07 [M-2Na]^-, 2127.06 [M - 3Na]^-,

OTHER SPECTRA	:

CHROMATOGRAM DATA

SOURCE

Chemical Synthesis

CHEMICAL SYNTHESIS

The suitably protected sialyl-a-(2-6)-gangliotriose (III6NeuAc-GgOse) derivative was glycosylated with the phenyl 2-thioglycoside of sialic acid in the presence of N-iodosuccinimide (NIS) and trimethylsilyl trifluoromethanesulfonate (TMSOTf) in acetonitrile medium, giving the disialogangliotriose (III6NeuAcII3NeuAc-GgOse) derivative which contains both sialyl-a(2-6)-GalNAc and sialyl-a(2-3)-Gal structures. This pentasaccharide was efficiently synthesized by the coupling of (methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-a-D-galacto-2-nonulopyranosylonate)-(2-6)-2-deoxy-4,6-O-isopropylidene-2-phthalimido-D-galactopyranosyl trichloroacetimidate with 2-(trimethylsilyl)ethyl (methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-a-D-galacto-2-nonulopyranosylonate)-(2-3)-(2,6-di-O-benzyl-b-D-galactopyranosyl)-(1-4)-2,3,6-tri-O-benzyl-b-D-glucopyranoside,
followed by conversion of the phthalimido group to the acetamido group. O-Deisopropylidenation and further glycosylation with methyl (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, promoted by dimethyl(methylthio)sulfonium triflate (DMTST), gave the desired trisialogangliotetraose (IV3NeuAcIII6NeuAcII3NeuAc-GgOse4) derivative, which was converted stepwise into the title ganglioside GT1aa- by the introduction of the ceramide part and then complete deprotection. (Ref. 3031)

METABOLISM

GENETIC INFORMATION

NOTE

LCB d18:1

REFERENCES

[3031]

AUTHOR	:	Ito, H., Ishida, H., Kiso, M., and Hasegawa, A.
TITLE	:	First total synthesis of ganglioside GT1a alpha PubMed ID:9679279
JOURNAL	:	Carbohydr Res.
VOL	:	306 PAGE : 581-585 (1998)

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