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Sphingosine (2-amino-4-octadecene-1,3-diol) is an 18-carbon amino alcohol
Amino alcohol

Amino alcohols are organic compounds that contain both an amine functional group and an alcohol functional group....
 with an unsaturated hydrocarbon chain, which forms a primary part of sphingolipid
Sphingolipid

Sphingolipids are a class of lipids derived from the aliphatic amino alcohol sphingosine. These compounds are ubiquitous, playing important roles in signal transmission and cell recognition....
s, a class of cell membrane
Cell membrane

The cell membrane is the interface between the cellular machinery inside the cell and the fluid outside.It is a semipermeable lipid bilayer found in all cell ....
 lipid
Lipid

Lipids are broadly defined as any fat-soluble , naturally-occurring molecule, such as fats, oils, waxes, cholesterol, sterols, fat-soluble vitamins , monoglycerides, diglycerides, phospholipids, and others....
s that include sphingomyelin
Sphingomyelin

Sphingomyelin, , is a type of sphingolipid found in animal cell membranes, especially in the membranous myelin sheath which surrounds some nerve cell axons....
, an important phospholipid
Phospholipid

File:Phospholipid.svgFile:phospholipid_structure.pngFile:Phosphatidyl-Choline.svgPhospholipids are a class of lipids and are a major component of all cell membranes....
.

ngosine can be phosphorylated
Phosphorylation

Phosphorylation is the addition of a phosphate group to a protein or other organic molecule. Protein phosphorylation in particular plays a significant role in a wide range of cellular processes....
 in vivo via two kinases, sphingosine kinase
Sphingosine Kinase

Sphingosine kinase is a conserved lipid kinase that catalyzes formation Sphingosine-1-phosphate from the precursor sphingolipid sphingosine. Sphingolipid metabolites, such as ceramide, sphingosine and sphingosine-1-phosphate, are lipid signaling involved in diverse cellular processes....
 type 1 and sphingosine kinase type 2. This leads to the formation of sphingosine-1-phosphate
Sphingosine-1-phosphate

Sphingosine-1-phosphate is a signaling sphingolipid. It is also referred to as a bioactive lipid mediator. Sphingolipids at large form a class of lipids characterized by a particular aliphatic aminoalcohol which is sphingosine....
, a potent signaling lipid
Lipid signaling

Lipid signaling, broadly defined, refers to any biological signaling event involving a lipid messenger that binds and activates a Receptor . Lipid signaling is thought to be qualitatively different from other classical signaling paradigms because lipids can freely diffuse through membranes....
.

Sphingolipid metabolites, such as ceramide
Ceramide

Ceramides are a family of lipid molecules. A ceramide is composed of sphingosine and a fatty acid. Ceramides are found in high concentrations within the cell membrane of cells....
, sphingosine and sphingosine-1-phosphate
Sphingosine-1-phosphate

Sphingosine-1-phosphate is a signaling sphingolipid. It is also referred to as a bioactive lipid mediator. Sphingolipids at large form a class of lipids characterized by a particular aliphatic aminoalcohol which is sphingosine....
, are lipid signaling
Lipid signaling

Lipid signaling, broadly defined, refers to any biological signaling event involving a lipid messenger that binds and activates a Receptor . Lipid signaling is thought to be qualitatively different from other classical signaling paradigms because lipids can freely diffuse through membranes....
 molecules involved in diverse cellular processes.

ngosine is synthesized from palmitoyl CoA
Palmitoyl CoA

Palmitoyl CoA is a molecule used to synthesize sphingosine:Additional imagesPalmitoyl CoA is a Acyl-CoA thioester...
 and serine
Serine

Serine is an organic compound with the chemical formula hydrogenoxygen2carbonCHCH2OH....
 in a condensation required to yield dehydrosphingosine.

Dehydrosphingosine is then reduced by NADPH to dihydrosphingosine, 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.






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Encyclopedia


Sphingosine (2-amino-4-octadecene-1,3-diol) is an 18-carbon amino alcohol
Amino alcohol

Amino alcohols are organic compounds that contain both an amine functional group and an alcohol functional group....
 with an unsaturated hydrocarbon chain, which forms a primary part of sphingolipid
Sphingolipid

Sphingolipids are a class of lipids derived from the aliphatic amino alcohol sphingosine. These compounds are ubiquitous, playing important roles in signal transmission and cell recognition....
s, a class of cell membrane
Cell membrane

The cell membrane is the interface between the cellular machinery inside the cell and the fluid outside.It is a semipermeable lipid bilayer found in all cell ....
 lipid
Lipid

Lipids are broadly defined as any fat-soluble , naturally-occurring molecule, such as fats, oils, waxes, cholesterol, sterols, fat-soluble vitamins , monoglycerides, diglycerides, phospholipids, and others....
s that include sphingomyelin
Sphingomyelin

Sphingomyelin, , is a type of sphingolipid found in animal cell membranes, especially in the membranous myelin sheath which surrounds some nerve cell axons....
, an important phospholipid
Phospholipid

File:Phospholipid.svgFile:phospholipid_structure.pngFile:Phosphatidyl-Choline.svgPhospholipids are a class of lipids and are a major component of all cell membranes....
.

Functions

Sphingosine can be phosphorylated
Phosphorylation

Phosphorylation is the addition of a phosphate group to a protein or other organic molecule. Protein phosphorylation in particular plays a significant role in a wide range of cellular processes....
 in vivo via two kinases, sphingosine kinase
Sphingosine Kinase

Sphingosine kinase is a conserved lipid kinase that catalyzes formation Sphingosine-1-phosphate from the precursor sphingolipid sphingosine. Sphingolipid metabolites, such as ceramide, sphingosine and sphingosine-1-phosphate, are lipid signaling involved in diverse cellular processes....
 type 1 and sphingosine kinase type 2. This leads to the formation of sphingosine-1-phosphate
Sphingosine-1-phosphate

Sphingosine-1-phosphate is a signaling sphingolipid. It is also referred to as a bioactive lipid mediator. Sphingolipids at large form a class of lipids characterized by a particular aliphatic aminoalcohol which is sphingosine....
, a potent signaling lipid
Lipid signaling

Lipid signaling, broadly defined, refers to any biological signaling event involving a lipid messenger that binds and activates a Receptor . Lipid signaling is thought to be qualitatively different from other classical signaling paradigms because lipids can freely diffuse through membranes....
.

Sphingolipid metabolites, such as ceramide
Ceramide

Ceramides are a family of lipid molecules. A ceramide is composed of sphingosine and a fatty acid. Ceramides are found in high concentrations within the cell membrane of cells....
, sphingosine and sphingosine-1-phosphate
Sphingosine-1-phosphate

Sphingosine-1-phosphate is a signaling sphingolipid. It is also referred to as a bioactive lipid mediator. Sphingolipids at large form a class of lipids characterized by a particular aliphatic aminoalcohol which is sphingosine....
, are lipid signaling
Lipid signaling

Lipid signaling, broadly defined, refers to any biological signaling event involving a lipid messenger that binds and activates a Receptor . Lipid signaling is thought to be qualitatively different from other classical signaling paradigms because lipids can freely diffuse through membranes....
 molecules involved in diverse cellular processes.

Synthesis

Sphingosine is synthesized from palmitoyl CoA
Palmitoyl CoA

Palmitoyl CoA is a molecule used to synthesize sphingosine:Additional imagesPalmitoyl CoA is a Acyl-CoA thioester...
 and serine
Serine

Serine is an organic compound with the chemical formula hydrogenoxygen2carbonCHCH2OH....
 in a condensation required to yield dehydrosphingosine.

Dehydrosphingosine is then reduced by NADPH to dihydrosphingosine, 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.

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