N-Hexanoyl-L-threo-sphingosine

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