N-Hexanoyl-L-threo-sphingosineN-Hexanoyl-L-threo-sphingosine
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N-Hexanoyl-L-threo-sphingosine

N-C6:0-L-threo-Ceramide

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
Cat# Size Price Qty Buy
1828 1 mg £178.13

Additional Information

Property Value or Rating
Product Size 1 mg
Manufacturer Matreya, LLC
Empirical Formula C24H47NO3
CAS# 189894-80-2
Formula Weight 397.6
Solvent none
Source synthetic
Purity 98+%
Analytical Methods TLC, GC
Natural Source Synthetic
Solubility chloroform, ethanol, DMSO, DMF (up to 5mg/ml)
Physical Appearance A neat solid
Storage -20°C
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

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