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L-erythro-Dihydrosphingosine

CATALOG # 1846

Specifications

  • Catalog #:1846
  • Scientific Name:L-erythro-Dihydrosphingosine
  • Common Name:L-erythro-Sphinganine, C18 chain
  • Empirical Formula:C18H39NO2
  • CAS#:6036-76-6
  • SDS:View Safety Data Sheet
  • Data Sheet:View Data Sheet
  • Formula Weight:301
  • Unit:1 mg
  • Solvent:none
  • Source:synthetic
  • Purity:98+%
  • Analytical Methods:TLC, GC; identity confirmed by MS
  • Solubility:chloroform, methanol, ethanol, DMSO
  • Physical Appearance:solid
  • Storage:-20°C
  • Dry Ice:No
  • Hazardous:No

Description

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
Price $155.00

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