Sphingosine
Sphingosine
Chemical compound
Sphingosine (2-amino-4-trans-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.
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| Preferred IUPAC name
(2S,3R,4E)-2-Aminooctadec-4-ene-1,3-diol | |
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| ECHA InfoCard | 100.004.230  |
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| Properties | |
| C18H37NO2 | |
| Molar mass | 299.499 g·mol−1 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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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 ceramides, sphingosine and sphingosine-1-phosphate, are lipid signaling molecules involved in diverse cellular processes.
Sphingosine is synthesized from palmitoyl CoA and serine in a condensation required to yield dihydrosphingosine.
Dehydrosphingosine is then reduced by NADPH to dihydrosphingosine (sphinganine), acylated to dihydroceramide finally oxidized by FAD to ceramide. Sphingosine is then solely formed via degradation of sphingolipid in the lysosome.
- Sphingolipidoses
- General structures of sphingolipids
- 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, Herbert E.; Glick, Francis J.; Norris, William P.; Phillips, George E. (1947). "Biochemistry of the sphingolipides. III. Structure of sphingosine". J. Biol. Chem. 170 (1): 285–295. doi:10.1016/S0021-9258(17)34955-4.
- Sphingosine at the U.S. National Library of Medicine Medical Subject Headings (MeSH)