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Glycosphingolipid


DATA No : GSG3051 INFORMANT : Hideharu Ishida

NAME : 3-sulfo-GalCer

COMMON NAME: sulfatide
SYMBOL:
FORMULA: C42H82NNaO11S MOL.WT (average) : 832.156


Download ChemDraw structure data
BIOLOGICAL ACTIVITY
Sulfatide does not support MAG-mediated adhesion.(Ref. 3040)
Sulfatide is a ligand for a lymphocyte homing receptor, L-selectin (LECAM-1), binding epitope in sulfated sugar chain.(Ref. 3066)
Sulfatide has significant in vivo protective effects in neutrophil and selectin-dependent models of lung injury.(Ref. 3067)
Sulfatide showed inhbitory activity on B cell proliferation and Ig production as a ligand for L-selectin.(Ref. 3068)
Sulfatide showed in vitro and in vivo selectin-blocking activities(Ref. 3069)
PHYSICAL AND CHEMICAL PROPERTIES
MELTING POINT:217-219deg(decomp)(Ref. 3053)

BOILING POINT:

REFRACTIVE INDEX:

OPTICAL ROTATION:

DENSITY:

SOLUBILITY:
SPECTRAL DATA
UV SPECTRA:

IR SPECTRA:

NMR SPECTRA:1D 1H-NMR (Ref. 3053)

MASS SPECTRA:

OTHER SPECTRA:ion-spray MS (negative ion mode): m/z 806.5 [M-Na]-, (positive ion mode): m/z 808.5 [M-Na+2H]-
CHROMATOGRAM DATA

SOURCE
Chemical Synthesis
CHEMICAL SYNTHESIS
The 3-O-levulinoyl derivative of galactopyranosyl trichloroacetimidate was coupled with (2S,3R,4E)-3-O-acetyl-2-octadecanamido-4-octadecene-1,3-diol. The resulting glycolipid was transformed, by selective removal of the levulinoyl group, and successive sulfation and de-O-acylation, into the sulfatide.(Ref. 3053)
METABOLISM

GENETIC INFORMATION

NOTE
Fatty acid 18:0

LCB d18:1
REFERENCES
[3040]
AUTHOR:Yang, L. J., Zeller, C. B., Shaper, N. L., Kiso, M., Hasegawa, A., Shapiro, R. E., and Schnaar, R. L.
TITLE:Gangliosides are neuronal ligands for myelin-associated glycoprotein PubMed ID:8570640
JOURNAL:Proc Natl Acad Sci U S A.
VOL:93 PAGE : 814-818 (1996)
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[3053]
AUTHOR:Tanahashi, E., Murase, K., Shibuya, M., Igarashi, Y., Ishida, H., Hasegawa, A., and Kiso, M.
TITLE:Synthetic studies on selectin ligands/inhibitors: a systematic synthesis of sulfatide and its higher congeners carrying 2-(tetradecyl)hexadecyl group as a ceramide substitute.
JOURNAL:J. Carbohydr. Chem.
VOL:166 PAGE : 831 -858 (1997)
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[3066]
AUTHOR:Suzuki, Y., Toda, Y., Tamatani, T., Watanabe, T., Suzuki, T., Nakao, T., Murase, K., Kiso, M., Hasegawa, A., Tadano-Aritomi, K., Ishizuka, I., and Miyasaka, M.
TITLE:Sulfated glycolipids are ligands for a lymphocyte homing receptor, L-selectin (LECAM-1), binding epitope in sulfated sugar chain. PubMed ID:7678958
JOURNAL:Biochem. Biophys. Res. Commun.
VOL:190 PAGE : 426 -434 (1993)
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[3067]
AUTHOR:Mulligan, M. S., Miyasaka, M., Suzuki, Y., Kawashima, H., Iizuka, M., Hasegawa, A., Kiso, M., Warner, R. L., Ward, P. A., Suzuki, T., et al.
TITLE:Anti-inflammatory effects of sulfatides in selectin-dependent acute lung injury PubMed ID:8527408
JOURNAL:Int Immunol.
VOL:7 PAGE : 1107-1113 (1995)
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[3068]
AUTHOR:Konno, A., Nunogami, K., Wada, T., Yachie, A., Suzuki, Y., Takahashi, N., Suzuki, T., Miyamoto, D., Kiso, M., Hasegawa, A., et al.
TITLE:Inhibitory action of sulfatide, a putative ligand for L-selectin, on B cell proliferation and Ig production PubMed ID:8982775
JOURNAL:Int Immunol.
VOL:8 PAGE : 1905-1913 (1996)
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[3069]
AUTHOR:Mulligan, M. S., Warner, R. L., Lowe, J. B., Smith, P. L., Suzuki, Y., Miyasaka, M., Yamaguchi, S., Ohta, Y., Tsukada, Y., Kiso, M., et al.
TITLE:In vitro and in vivo selectin-blocking activities of sulfated lipids and sulfated sialyl compounds PubMed ID:9645605
JOURNAL:Int Immunol.
VOL:10 PAGE : 569-575 (1998)
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Last updated June 19, 2007. Copyright © 1989-2007 Japanese Conference on the Biochemistry of Lipids (JCBL). All rights reserved.