N-Acetyl-L-erythro-sphingosine

CATALOG # 1847
Amount 1 mg
Price $150.00
Qty
 
C20H39NO3
  • Catalog #:1847
  • Scientific Name:N-Acetyl-L-erythro-sphingosine
  • Common Name:N-C2:0-L-erythro-Ceramide
  • Empirical Formula:C20H39NO3
  • CAS#150338-90-2
  • SDSView Safety Data Sheet
  • Data Sheet:View Data Sheet
  • Formula Weight:342
  • Unit:1 mg
  • Solvent:none
  • Source:synthetic
  • Purity:98+%
  • Analytical Methods:TLC, GC
  • Solubility:chloroform, ethanol, methanol, DMSO, DMF (up to 5 mg/ml)
  • Physical Appearance:solid
  • Storage:-20°C
  • Dry Ice:No
  • Hazardous:No
  • Literature References:Application Notes:

    This product contains an L-erythro-sphingosine containing an acetic amide linkage and is useful for comparison studies against the natural D-erythro isomer. This product is also very useful as an internal standard1,2 and contains a short-chain fatty acid enabling it to enter easily into cells. L-erythro-Sphingosine is an inactive or less active isomer of the naturally occurring D-erythro-sphingosine. Natural sphingosine induces dephosphorylation of retinoblastoma gene product and inhibits cell growth while L-erythro-sphingosine is 5-8-fold less active. However, the L-erythro-sphingosine is taken up by cells to the same extent as the natural sphingosine indicating that cellular uptake was not the factor influencing activity.3 L-erythrosphingosine, along with other sphingosine isomers, has been found to be an activator of 3-Phosphoinositide-dependent kinase 1.

    References:
    1. T. Cunningham et al. “Product inhibition of secreted phospholipase A2 may explain lysophosphatidylcholines' unexpected therapeutic properties” Journal of Inflammation, 5:17 doi:10.1186/1476-9255-5-17, 2008
    2. T. Cunninghame et al “Uncompetitive Phospholipase A2 Inhibition by CHEC Sequences Including Oral Treatment of Experimental Autoimmune Myeloencephalitis” The Open Enzyme Inhibition Journal, vol. 2 pp. 1-7, 2009
    3. 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