N-Hexanoyl-L-threo-sphingosine

CATALOG # 1828
Amount 1 mg
Price $190.00
Qty
 
C24H47NO3
  • Catalog #:1828
  • Scientific Name:N-Hexanoyl-L-threo-sphingosine
  • Common Name:N-C6:0-L-threo-Ceramide
  • Empirical Formula:C24H47NO3
  • CAS#189894-80-2
  • SDSView Safety Data Sheet
  • Data Sheet:View Data Sheet
  • Formula Weight:398
  • Unit:1 mg
  • Solvent:none
  • Source:synthetic
  • Purity:98+%
  • Analytical Methods:TLC, GC; identity confirmed by MS
  • Solubility:chloroform, ethanol, DMSO, DMF (up to 5mg/ml)
  • Physical Appearance:solid
  • Storage:-20°C
  • Dry Ice:No
  • Hazardous:No
  • Literature References:Application Notes:

    This product is the non-natural L-threo stereoisomer of ceramide. Natural D-erythro ceramide is a critical compound in cells both as a free ceramide and incorporated into more complex sphingolipids. L-threo-ceramides demonstrate a different metabolic functionality from natural ceramides. They have been shown to be metabolized to sphingomyelin but not to glucosylceramide.1 Another non-natural stereoisomer, L-erythro ceramide, is not metabolized to any sphingolipid. In contrast to natural ceramides L-threo ceramides are unable to antagonize the disruptive effects of fumonisin B1 on axon growth2 but it is able to activate intracellular pathways and induces apoptosis.3 The deacylated form of ceramide, sphingosine, also has many critical cellular functions. L-threo-sphingosine, along with other sphingosine isomers, has been found to be an activator of 3-Phosphoinositide-dependent kinase-14 and inhibits protein kinase C a little more potently than D-erythro-sphingosine.5

    References:
    1. K. Venkataraman and H. Futerman “Comparison of the metabolism of L-erythro- and L-threo-sphinganines and ceramides in cultured cells and in subcellular fractions” Biochim Biophys Acta, vol. 1530 pp. 219-226, 2001
    2. A. Schwarz and A. Futerman “Distinct Roles for Ceramide and Glucosylceramide at Different Stages of Neuronal Growth” The Journal of Neuroscience, vol. 17 pp. 2929-2938, 1997
    3. A. Bielawska et al. “Selectivity of ceramide-mediated biology—lack of activity of erythrodihydroceramide” J Biol Chem, vol. 268 pp. 26226 –26232, 1993
    4. C. King et al. “Sphingosine Is a Novel Activator of 3-Phosphoinositide-dependent Kinase 1” The Journal of Biological Chemistry, vol. 275(24) pp. 18108-18113, 2000
    5. V. Stevens et al. “Structural requirements for long-chain (sphingoid) base inhibition of protein kinase C in vitro and for the cellular effects of these compounds” Biochemistry, vol. 28, 3138-3145, 1989