Sphingosine

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ImageFile = Sphingosine-2D-skeletal.png OtherNames =
Formula = C18H37NO2
PubChem = 1104
MolarMass= 299.492
CASNo = 123-78-4
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Sphingosine (2-amino-4-octadecene-1,3-diol) is an 18-carbon amino alcohol with an unsaturated hydrocarbon chain, which forms a primary part of sphingolipids, a class of cell membrane lipids that include sphingomyelin, an important phospholipid.

Functions

Sphingosine can be phosphorylated in vivo via two kinases, sphingosine kinase type 1 and sphingosine kinase type 2. This leads to the formation of sphingosine-1-phosphate, a potent signaling lipid.

Sphingolipid metabolites, such as ceramide, sphingosine and sphingosine-1-phosphate, are lipid signaling molecules involved in diverse cellular processes.

Synthesis

Sphingosine is synthesized from palmitoyl CoA and serine in a condensation required to yield dehydrosphingosine.

Dehydrosphingosine is then reduced by NADPH to dihydrosphingosine, and finally oxidized by FAD to sphingosine.

There is no direct route of synthesis from sphinganine to sphingosine it has to be acylated first to dihydroceramide which is then dehydrogenated to ceramide. Sphngosine is formed via degradation of sphingolipid in the lysosome.

References

* [http://www.biochemj.org/bj/371/0243/bj3710243.htm article]

External links

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