Glycosphingolipid

DATA No : GSG3051 INFORMANT : Hideharu Ishida

NAME : 3-sulfo-GalCer

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

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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	:	217-219(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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