Back to HOME

Glycosphingolipid


DATA No : GSG3025 INFORMANT : Hideharu Ishida

NAME : 3-sulfoglucuronylb1-3galactosyl-b1-4-N-acetyl-glucosaminyl-b1-3galactosyl-b1-4glucosylceramide

COMMON NAME: 3-sulfoglucuronylparagloboside
SYMBOL: SGPG
FORMULA: C74H131N2O32SNa2 MOL.WT (average) : 1638.872


Download ChemDraw structure data
BIOLOGICAL ACTIVITY

PHYSICAL AND CHEMICAL PROPERTIES
MELTING POINT:

BOILING POINT:

REFRACTIVE INDEX:

OPTICAL ROTATION:

DENSITY:

SOLUBILITY:
SPECTRAL DATA
UV SPECTRA:

IR SPECTRA:

NMR SPECTRA:

MASS SPECTRA:FAB-MS (negative ion mode); m/z 1615.85 (M-Na)-, 1637.66 (M-H)- (Ref. 3016)

OTHER SPECTRA:
CHROMATOGRAM DATA

SOURCE
Chemical Synthesis
CHEMICAL SYNTHESIS
Methyl (4-O-acetyl-2-O-benzoyl-3-O-levulinoyl-a-D-glucopyranosyl trichloroacetimidate)uronate) was prepared from methyl [2-(trimethylsilyl)ethyl b-D-glucopyranosid]uronate via selective 4-O-acetylation, 2-O-benzoylation, 3-O-levulinoylation, removal of the 2-(trimethylsilyl)ethyl group and imidate formation. The coupling of the donor with 2-(trimethylsilyl)ethyl 2,4,6-tri-O-benzyl-b-D-galactopyranoside using trimethylsilyl trifluoromethanesulfonate gave 2-(trimethylsilyl)ethyl O-(methyl 4-O-acetyl-2-O-ben-zoyl-3-O-levulinoyl-b-D-glucopyranosyluronate)-(1-3)-2,4,6-tri-O-benzyl-b-D-galact-opyranoside, which was transformed via removal of the benzyl group, benzoylation, removal of the 2-(trimethylsilyl)ethyl group and imidate formation into the disaccharide donor. On the other hand, 2-(trimethylsilyl)ethyl O-(2-acetamido-3,6-di-O-benzyl-2-deoxy-b-D-glucopyranosyl)-(1-3)-O-(2,4,6-tri-O-benzyl-b-D-galactopyranosyl)-(1-4)-2,3,6-tri-O-benzyl-b-D-glucopyranoside as the acceptor was prepared from 2-(trimethylsilyl)ethyl
3,6-di-O-benzyl-2-deoxy-2-phthalimido-b-D-glucopyranoside via O-acetylation, removal of the 2-(trimethylsilyl)ethyl group, imidate formation, coupling with 2-(trimethylsilyl)ethyl O-(2,4,6-tri-O-benzyl-b-D-galactopyranosyl)-(1-4)-2,3,6-tri-O-benzyl-b-D-glucopyrano-side, removal of the O-acetyl and N-phthaloyl group followed by N-acetyla-tion. Condensation of thedisaccharide donor with the trisaccharide acceptor using trimethylsilyl trifluoromethanesulfonate afforded the desired pentasaccharide, which was transformed by removal of the benzyl group, O-acetylation, removal of the 2-(trimethylsilyl)ethyl group and imidate formation into the pentasaccharide donor. Glycosylation of (2S,3R,4E)-2-azido-3-O-benzoyl-4-octadecene-1,3-diol withthe imidate gave the desired b-glycoside, which was transformed into the target compound, via reduction of the azido group, coupling with tetracosanoic acid, selective removal of the levulinoyl group, O-sulfation, hydrolysis of the methyl ester group and O-deacylation.(Ref. 3016)
METABOLISM

GENETIC INFORMATION

NOTE
Fatty acid C24:0

LCB d18:1
REFERENCES
[3016]
AUTHOR:Isogai, Y., Kawase, T., Ishida, H., Kiso, M., and Hasegawa, A.
TITLE:Total synthesis of sulfated glucuronyl paraglobosides.
JOURNAL:Journal of Carbohydrate Chemistry
VOL:158 PAGE : 1001 -1023 (1996)
[TOP]

Last updated June 19, 2007. Copyright © 1989-2007 Japanese Conference on the Biochemistry of Lipids (JCBL). All rights reserved.