N-Octadecanoyl-L-erythro-sphingosineN-Octadecanoyl-L-erythro-sphingosine
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N-Octadecanoyl-L-erythro-sphingosine

N-C18:0-L-erythro-Ceramide; N-Stearoyl-L-erythro-sphingosine

This product is a high purity, non-natural L- erythro ceramide that is ideal as a standard and for biological studies. D-erythro ceramide is the natural ceramide isomer and is involved in many biological processes including induction of cell maturation, cell cycle arrest, terminal cell differentiation, cell senescence, and cell death.1 Natural sphingosine induces dephosphorylation of retinoblastoma gene product and inhibits cell growth while L-erythro-sphingosine is 5-8-fold less active. However, the Lerythro- sphingosine is taken up by cells to the same extent as the natural sphingosine indicating that cellular uptake was not the factor influencing activity.2 Both the natural D-erythro and the non-natural L-erythro and the D- and L-threo ceramides display similar effectiveness in inducing apoptotic damage in cells.3 The protein phosphatases PP1 and PP2A, which are involved in regulating apoptosis and cell growth, are activated by D-erythro ceramide but inhibited by L-threo, D-threo, and L-erythro ceramide.4 Both D-erythro and D-threo C2 ceramides have been found to be potent inducers of IL-6 production, while neither the L-threo or L-erythro stereoisomers of ceramide were effective.5 D- and L-erythro ceramide and D- and Lthreo ceramide are also comparably effective inhibitors of protein kinase C.6
Cat# Size Price Qty Buy
1850 1 mg £159.38

Additional Information

Property Value or Rating
Product Size 1 mg
Manufacturer Matreya, LLC
Empirical Formula C36H71NO3
Formula Weight 566
Solvent none
Source synthetic
Purity 98+%
Analytical Methods TLC, GC
Natural Source Synthetic
Solubility chloroform, ethanol, DMSO, DMF (up to 5mg/ml)
Physical Appearance A neat solid
Storage -20°C
References

1. N. S. Radin, “Killing tumours by ceramide-induced apoptosis: a critique of available drugs” Biochemical Journal, Vol. 371 pp. 243-256, 2003 
2. Y. Hannun et al. “Stereoselectivity of Induction of the Retinoblastoma Gene Product (pRb) Dephosphorylation by D-erythro-Sphingosine Supports a Role for pRb in Growth Suppression by Sphingosine” Biochemistry, vol. 34 pp. 1885-1892, 1995 
3. W. Jarvis et al. “Induction of Apoptosis and Potentiation of Ceramide-mediated Cytotoxicity by Sphingoid Bases in Human Myeloid Leukemia Cells” The Journal of Biological Chemistry, Vol. 271 pp. 8275-8284, 1996 
4. C. Chalfant et al. “Long Chain Ceramides Activate Protein Phosphatase-1 and Protein Phosphatase-2A Activation is Stereospecific and Regulated by Phosphatidic Acid” The Journal of Biological Chemistry, Vol. 274 pp. 20313-20317, 1999 
5. S. Laulederkind et al. “Ceramide Induces Interleukin 6 Gene Expression in Human Fibroblasts” The Journal of Experimental Medicine, Vol. 182 pp. 599-604, 1995 
6. T. Ariga et al. “Role of sphingolipid-mediated cell death in neurodegenerative diseases” Journal of Lipid Research, Vol. 39 pp. 1-16, 1998

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