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L-threo-Sphingosine, C18 chain

L-threo-Sphingosine is an inactive or less active isomer of the naturally occurring D-erythro-sphingosine. Natural sphingosine induces dephosphorylation of retinoblastoma gene products and inhibits cell growth while L-threo-sphingosine is less active. However, the L-threo-sphingosine is taken up by cells to the same extent as the natural sphingosine indicating that cellular uptake was not the factor influencing activity.1 L-threo-sphingosine, along with other sphingosine isomers, has been found to be an activator of 3-Phosphoinositide-dependent kinase-1.2 Natural D-erythro-sphingosine is a positive regulator of cell growth in fibroblasts whereas L-threo-sphingosine has no regulatory effect.3 However, non-natural stereoisomers of sphingosine are not always inactive; L-threo-sphingosine has been shown to inhibit protein kinase C a little more potently than D-erythro-sphingosine.4 Sphingosine is a characteristic structural unit of many sphingolipids such as ceramides, gangliosides, globosides, sulfatides, sphingomyelin, and others. 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. Sphingosine can be phosphorylated via two kinases to form sphingosine-1-phosphate, which has important signaling functions. While sphingosines and ceramides can induce apoptosis, sphingosine-1-phosphate can promote cell survival or proliferation. Sphingosine has been shown to cause an increase in the cytoplasmic calcium level of cells.
Cat# Size Price Qty Buy
1806 10 mg £290.70

Additional Information

Property Value or Rating
Product Size 10 mg
Manufacturer Matreya, LLC
Empirical Formula C18H37NO2
CAS# 25695-95-8
Formula Weight 299.5
Solvent none
Source synthetic
Purity 98+%
Analytical Methods TLC, GC
Natural Source Synthetic
Solubility ethanol, methanol, chloroform, DMSO
Physical Appearance A neat solid
Storage -20°C

1. 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 
2. 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 
3. S. Spiegel et al. “Stereospeci~cityo f Sp~ingosine-indu~eIdnt racellular Calcium Mobilization and Cellular Proliferation” Journal of Biological Chemistry, vol. 269 pp. 17924-17930, 1994 
4. 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

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