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Glycosphingolipid


DATA No : GSG3007 INFORMANT : Hideharu Ishida

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

COMMON NAME: sialyl-neolactotetraosylceramide/sialyl-paragloboside
SYMBOL:
FORMULA: C73H131N3O32 MOL.WT (average) : 1562.822


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BIOLOGICAL ACTIVITY
This ganglioside gave a negative reaction to a lymphocyte homing receptor, L-selectin (LECAM-1). (Ref. 3035)
A new monoclonal antibody directed to this ganglioside was prepared, and which was applied for detection of human gastrointestinal neoplasmas (Ref. 3050)
PHYSICAL AND CHEMICAL PROPERTIES
MELTING POINT:

BOILING POINT:

REFRACTIVE INDEX:

OPTICAL ROTATION:-3.8deg(Ref. 3004)

DENSITY:

SOLUBILITY:
SPECTRAL DATA
UV SPECTRA:

IR SPECTRA:(Ref. 3004)

NMR SPECTRA:1D 1H-NMR (Ref. 3004)

MASS SPECTRA:

OTHER SPECTRA:
CHROMATOGRAM DATA

SOURCE
Chemical Synthesis
CHEMICAL SYNTHESIS
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-benzoyl-1-thio-b-D-galactopyranoside, the key glycosyl donor, was prepared, from the 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)-6-O-benzoyl-b-D- galactopyranoside, via benzoylation, replacement of the 2-(trimethylsilyl)ethyl group by acetyl, and introduction of the methylthio group with methylthiotrimethylsilane. Coupling of 2-(trimethylsilyl)ethyl 2,3,6,2',4',6'-hexa-O-benzyl-b-D-galactopyranoside, prepared from 2-(trimethylsilyl)ethyl b-D-lactoside via selective 3'-O-(4-methyoxybenzylation), benzylation, and selective removal of the 4-methyoxybenzyl group, with 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimide-D-glucopyranosyl bromide gave a trisaccharide derivative, from which the phthaloyl and O-acetyl groups were removed.
N-Acetylation then gave 2-(trimethylsilyl)ethyl O-(2-acetamido-2-deoxy-b-D-galactopyranosyl)-(1-3)-O-(2,4,6-tri-O-benzyl-b-D-galactopyranosyl)-(1-4)-2,3,6-tri-O-benzyl-b-D-glucopyranoside. Dimethyl(methylthio)sulfonium triflate promoted coupling of the disaccharide donor with the trisaccharide acceptor, prepared by 4,6-O-benzylidenation, 3-O-(4-methoxybenzylation) and reductive opening of the benzylidene acetal, gave the corresponding pentasaccharide derivatives 16 and 20 in good yields. This oligosacharide was converted into the corresponding a-trichloroacetimidates which, on coupling with (2S, 3R, 4E)-2-azido-3-O-benzoyl-4-octadecene-1,3-diol, gave the b-glycosides. Finally, the compound was transformed, via selective reduction of the azide group, condensation with octadecanoic acid, O-deacylation, and hydrolysis of the methyl ester group, into the final product.(Ref. 3004)
METABOLISM

GENETIC INFORMATION

NOTE
Fatty acid C18:0

LCB d18:1
REFERENCES
[3004]
AUTHOR:Kameyama, A., Ishida, H., Kiso, M., and Hasegawa, A.
TITLE:Stereoselective synthesis of sialyl-lactotetraosylceramide and sialylneolactotetraosylceramide PubMed ID:2379209
JOURNAL:Carbohydr Res.
VOL:200 PAGE : 269-285 (1990)
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[3035]
AUTHOR:Suzuki, Y., Toda, Y., Tamatani, T., Watanabe, T., Suzuki, T., Nakao, T., Murase, K., Kiso, M., Hasegawa, A., Tadano-Aritomi, K., et al.
TITLE:Sulfated glycolipids are ligands for a lymphocyte homing receptor, L-selectin (LECAM-1), binding epitope in sulfated sugar chain. PubMed ID:7678958
JOURNAL:Biochemical and biophysical research communications
VOL:190 PAGE : 426 -434 (1993)
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[3050]
AUTHOR:Suzuki, Y., Nishi, H., Hidari, K., Hirabayashi, Y., Matsumoto, M., Kobayashi, T., Watarai, S., Yasuda, T., Nakayama, J., Maeda, H., et al.
TITLE:A new monoclonal antibody directed to sialyl alpha 2-3lactoneotetraosylceramide and its application for detection of human gastrointestinal neoplasms PubMed ID:1864848
JOURNAL:J Biochem (Tokyo).
VOL:109 PAGE : 354-360 (1991)
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Last updated June 19, 2007. Copyright © 1989-2007 Japanese Conference on the Biochemistry of Lipids (JCBL). All rights reserved.