Application Notes:
This product is a high purity, well-defined, L-erythro-dihydrosphingosine which demonstrates unique properties as compared
with the natural D-erythro isomer and is therefore ideal for use in studies of dihydrosphingosine. Natural D-erythrodihydrosphingosine
is the precursor of dihydroceramide which is then desaturated to form ceramide. It is a critical
intermediate in the synthesis of many complex sphingoid bases and ceramide analogs. It has been found that
dihydrosphingosine can induce cell death in a number of types of malignant cells and it is being tested for its
pharmacological properties.1 Whereas both D-threo and L-threo-C2-dihydroceramide induced apoptosis in cells neither Derythro
nor L-erythro-C2-dihydroceramide showed activity.2 One report has concluded that all four of the enantiomers of
dihydrosphingsoine act as substrates for sphingosine kinase with only the natural D-erythro-dihydrosphingosine being
metabolized by sphinganine-1-phosphate lyase.3 However, another report concludes that only the erythro isomers of
dihydrosphingosine act as substrates for this enzyme with both of the threo isomers inhibiting its activity.4
References:
1. W. Zheng “Fenretinide increases dihydroceramide and dihydrosphingolipids due to inhibition of dihydroceramide desaturase” Georgia Institute of
Technology, 2006
2. A. Bielawska “Selectivity of Ceramide-Mediated Biology Lack of Activity of erythro-Dihydroceramide” Journal of Biological Chemistry, vol. 268 pp.
26226-26232, 1993
3. W. Stoffel and K. Bister “Stereospecificities in the metabolic reactions of the four isomeric sphinganines (dihydrosphingosines) in rat liver” Hoppe
Seylers Z Physiol Chem, vol. 354 pp. 169-181, 1973
4. B. Buehrer and R. Bell “Inhibition of Sphingosine Kinase in Vitro and in Platelets Implications for Signal Transduction Pathways” Journal of Biological
Chemistry, vol. 267 pp. 3154-3159, 1992