Glycosphingolipid

DATA No : GSG1085 INFORMANT : Kazuo Nakamura

NAME : NeuAc2-3Galb1-3(NeuAc2-6)GalNAcb1-4(NeuAc2-3)Galb1-4GlcCer

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

Download ChemDraw structure data

BIOLOGICAL ACTIVITY

Cholinergic-specific antigen Chol-1a-a (Reacted with anti-cholinergic neuron specific antibody) (Ref. 1028)
Monoclonal antibody: GGR-41 (reacted also with GQ1ba) (Ref. 1124)

PHYSICAL AND CHEMICAL PROPERTIES

MELTING POINT	:

BOILING POINT	:

REFRACTIVE INDEX	:

OPTICAL ROTATION	:

DENSITY	:

SOLUBILITY	:

SPECTRAL DATA

UV SPECTRA	:

IR SPECTRA	:

NMR SPECTRA	:	1D 1H-NMR (Ref. 1026/1028) [Spectrum 0002] HOHAHA (Ref. 1028) [Spectrum 0003]

MASS SPECTRA	:	INTACT FAB-MS [Spectrum 0001] (Ref. 1026/1028)

OTHER SPECTRA	:

CHROMATOGRAM DATA

TLC
[Chromatogram 0001]
[Chromatogram 0002] (Ref. 1026/1028)

SOURCE

Dogfish (shark) (Squalus acanthias) brain (Ref. 1026) bovine brain (Ref. 1028) Rat liver (Ref. 1123)
Rat: intense immunoreactivity was found in the neuropil of the spinal cord dorsal horn, spinal trigeminal nucleus, solitary tract nucleus, superior colliculus, interpeduncular nucleus, hypothalamus and septal area(Ref. 1124)

CHEMICAL SYNTHESIS

The suitably protected sialyl alpha-(2-->6) ganglioside was glycosylated with the phenylthioglycoside of sialic acid in the presence of N-iodosuccinimide (NIS)-trimethylsilyl trifluoromethanesulfonate (TMSOTf), followed by further glycosylation with the methyl thioglycoside promoted by dimethyl(methylthio)sulfonium triflate (DMTST), to give the heptasaccharide. The oligosaccharide obtained was converted into the title ganglioside by the introduction of ceramide and then complete deprotection. (Ref. 1128)

METABOLISM

GENETIC INFORMATION

NOTE

Fatty acids 16:0(15.0%), 16:1(9.3%), 18:0(8.6%), 18:1(9.0%), 22:1(38.4%), 24:0(13%), 24:1(6.7%) (Ref. 1026)

LCB d18:0(43%) , d18:1(57%) (Ref. 1026)

REFERENCES

[1026]

AUTHOR	:	Nakamura, K., Inagaki, F., and Tamai, Y.
TITLE	:	A novel ganglioside in dogfish brain. Occurrence of a trisialoganglioside with a sialic acid linked to N-acetylgalactosamine PubMed ID:3384822
JOURNAL	:	J Biol Chem.
VOL	:	263 PAGE : 9896-9900 (1988)

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[1028]

AUTHOR	:	Ando, S., Hirabayashi, Y., Kon, K., Inagaki, F., Tate, S., and Whittaker, V. P.
TITLE	:	A trisialoganglioside containing a sialyl alpha 2-6 N-acetylgalactosamine residue is a cholinergic-specific antigen, Chol-1 alpha PubMed ID:1587788
JOURNAL	:	J Biochem (Tokyo).
VOL	:	111 PAGE : 287-290 (1992)

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[1123]

AUTHOR	:	Irie, F., Hidari, K. I., Tai, T., Li, Y. T., Seyama, Y., and Hirabayashi, Y.
TITLE	:	Biosynthetic pathway for a new series of gangliosides, GT1a alpha and GQ1b alpha PubMed ID:8082783
JOURNAL	:	FEBS Lett.
VOL	:	351 PAGE : 291-294 (1994)

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[1124]

AUTHOR	:	Irie, F., Hashikawa, T., Tai, T., Seyama, Y., and Hirabayashi, Y.
TITLE	:	Distribution of cholinergic neuron-specific gangliosides (GT1a alpha and GQ1b alpha) in the rat central nervous system PubMed ID:7710562
JOURNAL	:	Brain Res.
VOL	:	665 PAGE : 161-166 (1994)

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[1128]

AUTHOR	:	Ito, H., Ishida, H., Kiso, M., and Hasegawa, A.
TITLE	:	First total synthesis of ganglioside GT1a alpha PubMed ID:9468624
JOURNAL	:	Carbohydr Res.
VOL	:	304 PAGE : 187-189 (1997)

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