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Wikipedia

Sphingosine

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.

Sphingosine
Names
Preferred IUPAC name
(2S,3R,4E)-2-Aminooctadec-4-ene-1,3-diol
Identifiers
  • 123-78-4 Y
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:16393 N
ChEMBL
  • ChEMBL67166 Y
ChemSpider
  • 4444047 Y
ECHA InfoCard 100.004.230
  • 2452
  • 5280335
UNII
  • NGZ37HRE42 Y
  • DTXSID90861763
  • 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
  • CCCCCCCCCCCCC/C=C/[C@H]([C@H](CO)N)O
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).
N verify (what is YN ?)

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 ceramides, 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 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.

See also

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, 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.

Additional images

External links

sphingosine, amino, trans, octadecene, diol, carbon, amino, alcohol, with, unsaturated, hydrocarbon, chain, which, forms, primary, part, sphingolipids, class, cell, membrane, lipids, that, include, sphingomyelin, important, phospholipid, namespreferred, iupac,. 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 Sphingosine NamesPreferred IUPAC name 2S 3R 4E 2 Aminooctadec 4 ene 1 3 diolIdentifiersCAS Number 123 78 4 Y3D model JSmol Interactive imageChEBI CHEBI 16393 NChEMBL ChEMBL67166 YChemSpider 4444047 YECHA InfoCard 100 004 230IUPHAR BPS 2452PubChem CID 5280335UNII NGZ37HRE42 YCompTox Dashboard EPA DTXSID90861763InChI 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 YKey WWUZIQQURGPMPG KRWOKUGFSA N YInChI 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 s1Key WWUZIQQURGPMPG KRWOKUGFBWSMILES CCCCCCCCCCCCC C C C H C H CO N OPropertiesChemical formula C 18H 37N O 2Molar mass 299 499 g mol 1Except where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa N verify what is Y N Infobox references Contents 1 Functions 2 Biosynthesis 3 See also 4 References 5 Additional images 6 External linksFunctions EditSphingosine 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 Biosynthesis EditSphingosine 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 See also EditDimethylsphingosine FingolimodReferences EditRadin 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 Additional images Edit Sphingolipidoses General structures of sphingolipidsExternal links EditSphingosine at the U S National Library of Medicine Medical Subject Headings MeSH Retrieved from https en wikipedia org w index php title Sphingosine amp oldid 1162208788, wikipedia, wiki, book, books, library,

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