D-erythro-Sphingosine, D9

CATALOG # 2079
Amount 1 mg
Price $385.00
Qty
 
D-erythro-Sphingosine, D9
  • Catalog #:2079
  • Scientific Name:D-erythro-Sphingosine, D9
  • Common Name:15,15,16,16,17,17,18,18,18-D9-2-Amino-octadec-4-ene-1,3-diol
  • Empirical Formula:C18H28D9NO2
  • SDSView Safety Data Sheet
  • Data Sheet:View Data Sheet
  • Formula Weight:309
  • Unit:1 mg
  • Solvent:none
  • Source:synthetic
  • Purity:98+%
  • Analytical Methods:TLC, GC, HPLC, identity confirmed by MS
  • Solubility:chloroform, ethanol, methanol, DMSO
  • Physical Appearance:solid
  • Storage:-20°C
  • Dry Ice:No
  • Hazardous:No
  • Literature References:Application Notes:

    This synthetic D-erythro-sphingosine contains nine deuterium atoms making it an ideal stable isotope-labeled standard for lipidomic studies using mass spectrometry. Stable isotope-labeled tracers are ideal for studies involving the metabolism and various metabolites of a lipid and can be used for the quantitative evaluation of major lipid pathways.1 Lipidomics has shown great success in the use of deuterium labeled compounds in identifying and quantifying individual molecular species by the use of tandem mass spectrometry.2 This deuterated sphingosine can also be used in the preparation of sphingolipids that are labeled on the sphingosine chain. In this way deuterated ceramides can be prepared that will not lose their label if the fatty acid is cleaved off in vivo and replaced by an alternate fatty acid. Sphingosine is a characteristic structural unit of many sphingolipids such as ceramides, gangliosides, globosides, sulfatides, sphingomyelin, and others.3,4 It is most abundant in nervous tissue and cell membranes. Sphingosine with an 18- carbon chain and a double bond at carbon 4 is the most abundant sphingosine in animal tissues. Lysosphingolipids inhibit protein kinase C activity resulting in the pathogenesis of sphingolipidoses such as Krabbe's disease and Gaucher's disease.5 Sphingosine can be phosphorylated via two kinases to form sphingosine-1-phosphate, which has important signaling functions. While sphingosines and ceramides can induce apoptosis,6 sphingosine-1-phosphate can promote cell survival or proliferation. Sphingosine has also been shown to cause an increase in the cytoplasmic calcium level of cells.

    References:
    1. Magkos, F. and Mittendorfer, B., “Stable isotope-labeled tracers for the investigation of fatty acid and triglyceride metabolism in humans in vivo” Clin Lipidol. Vol. 4 pp. 215–230, 2009
    2. Byun, H. and Bittman, R. Selective deuterium labeling of the sphingoid backbone: facile syntheses of 3,4, 5-trideuterio-d-erythro-sphingosine and 3- deuterio-d-erythro-sphingomyelin” Chem Phys Lipids, Vol. 163(8) pp. 809-813, 2010
    3. A. Merrill, Jr. “De Novo Sphingolipid Biosynthesis: A Necessary, but Dangerous, Pathway” The Journal of Biological Chemistry, Vol. 277(29) pp. 25843–25846, 2002
    4. J. Shayman “Sphingolipids” Kidney International, Vol. 58 pp. 11-26, 2000
    5. Y. Hannun and R. Bell “Lysosphingolipids inhibit protein kinase C: implications for the sphingolipidoses.” Vol. 235:4789 pp. 670, 1987
    6. V. Nava et al. “Sphingosine Enhances Apoptosis of Radiation-resistant Prostate Cancer Cells” Cancer Research, Vol. 60 pp. 4468-4474, 2000