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