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
sphingolipid
Sphingolipids are a class of lipids containing a backbone of sphingoid bases, which are a set of aliphatic amino alcohols that includes sphingosine. They were discovered in brain extracts in the 1870s and were named after the mythological sp ...
s, a class of
cell membrane
The cell membrane (also known as the plasma membrane or cytoplasmic membrane, and historically referred to as the plasmalemma) is a biological membrane that separates and protects the interior of a cell from the outside environment (the extr ...
lipid
Lipids are a broad group of organic compounds which include fats, waxes, sterols, fat-soluble vitamins (such as vitamins A, D, E and K), monoglycerides, diglycerides, phospholipids, and others. The functions of lipids include storing ...
s that include
sphingomyelin
Sphingomyelin (SPH, ) is a type of sphingolipid found in animal cell membranes, especially in the membranous myelin sheath that surrounds some nerve cell axons. It usually consists of phosphocholine and ceramide, or a phosphoethanolamine hea ...
, an important
phospholipid
Phospholipids are a class of lipids whose molecule has a hydrophilic "head" containing a phosphate group and two hydrophobic "tails" derived from fatty acids, joined by an alcohol residue (usually a glycerol molecule). Marine phospholipids typ ...
.
Functions
Sphingosine can be
phosphorylated
In biochemistry, phosphorylation is described as the "transfer of a phosphate group" from a donor to an acceptor. A common phosphorylating agent (phosphate donor) is ATP and a common family of acceptor are alcohols:
:
This equation can be writt ...
in vivo
Studies that are ''in vivo'' (Latin for "within the living"; often not italicized in English) are those in which the effects of various biological entities are tested on whole, living organisms or cells, usually animals, including humans, an ...
via two
kinases
In biochemistry, a kinase () is an enzyme that catalysis, catalyzes the transfer of phosphate groups from High-energy phosphate, high-energy, phosphate-donating molecules to specific Substrate (biochemistry), substrates. This process is known as ...
,
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
Ceramides are a family of waxy lipid molecules. A ceramide is composed of sphingosine and a fatty acid joined by an amide bond. Ceramides are found in high concentrations within the cell membrane of Eukaryote, eukaryotic cells, since they are co ...
s, sphingosine and
sphingosine-1-phosphate, are
lipid signaling
Lipid signaling, broadly defined, refers to any biological cell signaling event involving a lipid messenger that binds a protein target, such as a receptor (biochemistry), receptor, kinase or phosphatase, which in turn mediate the effects of these ...
molecules involved in diverse cellular processes.
Biosynthesis
Sphingosine is synthesized from
palmitoyl CoA and
serine
Serine
(symbol Ser or S) is an α-amino acid that is used in the biosynthesis of proteins. It contains an α- amino group (which is in the protonated − form under biological conditions), a carboxyl group (which is in the deprotonated − ...
in a condensation required to yield dihydrosphingosine.
Dehydrosphingosine is then reduced by
NADPH
Nicotinamide adenine dinucleotide phosphate, abbreviated NADP or, in older notation, TPN (triphosphopyridine nucleotide), is a cofactor used in anabolic reactions, such as the Calvin cycle and lipid and nucleic acid syntheses, which require N ...
to
dihydrosphingosine (sphinganine), acylated to dihydroceramide and finally oxidized by
FAD
A fad, trend, or craze is any form of collective behavior that develops within a culture, a generation, or social group in which a group of people enthusiastically follow an impulse for a short time period.
Fads are objects or behaviors tha ...
to ceramide. Sphingosine is then solely formed via degradation of sphingolipid in the lysosome.
Gallery
Image:Sphingolipidoses.svg, Sphingolipidoses
Image:Sphingolipids general structures.png, General structures of sphingolipid
Sphingolipids are a class of lipids containing a backbone of sphingoid bases, which are a set of aliphatic amino alcohols that includes sphingosine. They were discovered in brain extracts in the 1870s and were named after the mythological sp ...
s
See also
*
Dimethylsphingosine
*
Fingolimod
Literature
*
article*
External links
*
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Biomolecules
Diols
Amines
Alkene derivatives