Sphingosine

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Sphingosine
Molecular formula	C18H37NO2
Molar mass	299.492
CAS number	[123-78-4]
PubChem	1104
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and 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.

Contents 1 Functions 2 Synthesis 3 Additional images 4 References 5 External links

[edit] 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.

[edit] 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.

[edit] Additional images

Sphingolipid

[edit] References

• Radin N (2003). "Killing tumours by ceramide-induced apoptosis: a critique of available drugs". Biochem J 371 (Pt 2): 243-56. PMID 12558497.  article

[edit] External links

• MeSH Sphingosine

• Links to external chemical sources