Sphingosine

From Wikipedia, the free encyclopedia
Jump to: navigation, search
Sphingosine
Skeletal formula of sphingosine
Space-filling model of the sphingosine molecule
Names
IUPAC name
(2S,3R)-2-aminooctadec-4-ene-1,3-diol
Identifiers
123-78-4 YesY
ChEBI CHEBI:16393 N
ChEMBL ChEMBL67166 YesY
ChemSpider 4444047 YesY
2452
Jmol-3D images Image
PubChem 5280335
Properties
C18H37NO2
Molar mass 299.50 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
 N verify (what isYesY/N?)
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[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.

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[edit]

References[edit]

Additional images[edit]

External links[edit]