Sphingosine

Sphingosine
IUPAC name (2S,3R)-2-aminooctadec-4-ene-1,3-diol
Identifiers
CAS number	123-78-4 Y
PubChem	1104
ChemSpider	4444047 Y
ChEBI	CHEBI:26743 N
ChEMBL	CHEMBL67166 Y
Jmol-3D images	{{#if:CCCCCCCCCCCCC/C=C/[C@H]([C@H](CO)N)O|Image 1
SMILES CCCCCCCCCCCCC/C=C/[C@H]([C@H](CO)N)O
InChI InChI=1S/C18H37NO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-18(21)17(19)16-20/h14-15,17-18,20-21H,2-13,16,19H2,1H3/b15-14+/t17-,18+/m0/s1 Y Key: WWUZIQQURGPMPG-KRWOKUGFSA-N Y InChI=1/C18H37NO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-18(21)17(19)16-20/h14-15,17-18,20-21H,2-13,16,19H2,1H3/b15-14+/t17-,18+/m0/s1 Key: WWUZIQQURGPMPG-KRWOKUGFBW
Properties
Molecular formula	C18H37NO2
Molar mass	299.49 g mol−1
N (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
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.

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

• Dimethylsphingosine

References

• Radin N (2003). "Killing tumours by ceramide-induced apoptosis: a critique of available drugs". Biochem J 371 (Pt 2): 243–56. doi:10.1042/BJ20021878. PMC 1223313. PMID 12558497.  article
• Carter, H. E., F. J. Glick, W. P. Norris, and G. E. Phillips. 1947. Biochemistry of the sphingolipides. III. Structure of sphingosine. J. Biol. Chem. 170: 285–295

Additional images

• 

  Sphingolipidoses

• 

  General structures of sphingolipids

External links

• Sphingosine at the US National Library of Medicine Medical Subject Headings (MeSH)