Molecular formula C
18H 37NO 2
Molar mass 299.49 g mol
Except where noted otherwise, data are given for materials in their
standard state (at 25 °C (77 °F), 100 kPa)
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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 [ edit ]
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.
Biosynthesis [ edit ]
Sphingosine is synthesized from
palmitoyl CoA and serine in a condensation required to yield dehydrosphingosine.
Dehydrosphingosine is then reduced by
NADPH to dihydrosphingosine (sphinganine), 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. Sphingosine is formed via degradation of sphingolipid in the lysosome.
See also [ edit ]
References [ edit ]
Additional images [ edit ]
External links [ edit ]