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Sphingosine

Sphingosine
Skeletal formula of sphingosine
Space-filling model of the sphingosine molecule
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IUPAC name
(2S,3R)-2-aminooctadec-4-ene-1,3-diol
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123-78-4 7pxY
ChEBI CHEBI:16393 7pxN
ChEMBL ChEMBL67166 7pxY
ChemSpider 4444047 7pxY
Jmol-3D images Image
PubChem Template:Chembox PubChem/format
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C18H37NO2
Molar mass Lua error in Module:Math at line 495: attempt to index field 'ParserFunctions' (a nil value). g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
 14pxN verify (what is10pxY/10pxN?)
Infobox references

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.

Biosynthesis

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

Sphingosine synthesis

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

References

Additional images

External links