C24:1 3'-sulfo Galactosylceramide (d18:1/24:1(15Z)) Chemical Properties

storage temp. 

Store at -20°C

solubility 

Chloroform:Methanol (5:1): soluble

form 

A solid

C24:1 3'-sulfo Galactosylceramide (d18:1/24:1(15Z)) Usage And Synthesis

Description

C24:1 3’-sulfo Galactosylceramide is a member of the sulfatide class of glycolipids. It is the predominate sulfatide species in mature myelin, and it accumulates at a higher rate than C24 3’-sulfo galactosylceramide in rat cerebellum from seven to 32 days of age when active myelination occurs.¹ It interacts with C-type lectins and immunoglobulin-like receptors with the highest affinity for LMIR5.² It induces production of MCP-1 in basophils but not mast cells and increases the activation of NFAT in a reporter assay via LMIR5. C24:1 3’-sulfo Galactosylceramide is an immunodominant species in myelin, is bound by CD1d in vitro, and increases proliferation in isolated mouse splenocytes.³ It reduces symptoms and increases survival in a mouse model of chronic relapsing-remitting experimental autoimmune encephalomyelitis (EAE) when used at a dose of 20 μg.⁴ It also decreases the number of inflammatory lesions and infiltrating mononuclear cells in the lumbar spinal cord of EAE mice. As this product is derived from a natural source, there may be variations in the sphingoid backbone.

Definition

ChEBI: 1-(3-O-sulfo-beta-D-galactosyl)-N-[(15Z)-tetracos-15-enoyl]sphingosine is an N-acyl-beta-D-galactosylsphingosine having a sulfo group at the 3-position on the galactose ring and (15Z)-tetracos-15-enoyl as the N-acyl group. It has a role as an epitope. It is a galactosylceramide sulfate and a N-acyl-beta-D-galactosylsphingosine. It is a conjugate acid of a 1-(3-O-sulfo-beta-D-galactosyl)-N-[(15Z)-tetracos-15-enoyl]sphingosine(1-).

References

1. Marbois, B.N., Faull, K.F., Fluharty, A.L., et al. Analysis of sulfatide from rat cerebellum and multiple sclerosis white matter by negative ion electrospray mass spectrometry Biochim. Biophys. Acta 1484(1),59-70(2000).
2. Phongsisay, V., Iizasa, E., Hara, H., et al. 3-O-sulfo-β-D-galactose moiety of endogenous sulfoglycolipids is a potential ligand for immunoglobulin-like receptor LMIR5 Mol. Immunol. 63(2),595-599(2015).
3. Zajonc, D.M., Maricic, I., Wu, D., et al. Structural basis for CD1d presentation of a sulfatide derived from myelin and its implications for autoimmunity J. Exp. Med. 202(11),1517-1526(2005).
4. Maricic, I., Halder, R., Bischof, F., et al. Dendritic cells and anergic type I NKT cells play a crucial role in sulfatide-mediated immune regulation in experimental autoimmune encephalomyelitis J. Immunol. 193(3),1035-1046(2014).