Glycerol 3-phosphate

sn-Glycerol 3-phosphate

Names
IUPAC name (R)-2,3-dihydroxypropyl dihydrogen phosphate
Other names 1,2,3-propanetriol, 1-(dihydrogen phosphate), (2R)- D-glycerol 1-phosphate L-glycerol 3-phosphate L-α-glycerophosphate L-α-phosphoglycerol
Identifiers
CAS Number	17989-41-2 N
Jmol interactive 3D	Image
KEGG	C00093 N
MeSH	Alpha-glycerophosphoric+acid
PubChem	439162
InChI InChI=1S/C3H9O6P/c4-1-3(5)2-9-10(6,7)8/h3-5H,1-2H2,(H2,6,7,8)/t3-/m1/s1 Key: AWUCVROLDVIAJX-GSVOUGTGSA-N
SMILES C([C@H](COP(=O)(O)O)O)O
Properties
Chemical formula	C3H9O6P
Molar mass	172.074
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

sn-Glycerol 3-phosphate^[1] is a phosphoric ester of glycerol, which is a component of glycerophospholipids. Equally appropriate names in biochemical context include glycero-3-phosphate, 3-O-phosphonoglycerol, 3-phosphoglycerol.^[2] From a historical reason, it is also known as L-glycerol 3-phosphate, D-glycerol 1-phosphate, L-α-glycerophosphoric acid.^[2] It should not be confused with the similarly named glycerate 3-phosphate or glyceraldehyde 3-phosphate.

Biosynthesis and metabolism

Glycerol 3-phosphate is synthesized by reducing dihydroxyacetone phosphate (DHAP), a glycolysis intermediate, with glycerol-3-phosphate dehydrogenase. DHAP and thus glycerol 3-phosphate is also possible to be synthesized from amino acids and citric acid cycle intermediates via glyceroneogenesis pathway.

+ NAD(P)H + H⁺ → + NAD(P)⁺

It is also synthesized by phosphorylating glycerol generated upon hydrolyzing fats with glycerol kinase, and can feed into glycolysis or glyconeogenesis pathways.

+ ATP → + ADP

Glycerol 3-phosphate is a starting material for de novo synthesis of glycerolipids. In eukaryotes, it is first acylated on its sn-1 position by an ER- or mitochondrial membrane enzyme, glycerol-3-phosphate O-acyltransferase, and another acyl group is then added on the sn-2 position making phosphatidic acids.

+ Acyl-CoA → Lysophosphatidic acid + CoA

Some fungi have glycerol-1-phosphatase, which removes the phosphate group of glycerol 3-phosphate to generate glycerol. They can perform glycerol fermentation producing glycerol from glucose through glycolysis pathway.

+ H₂O → + Pi

Shuttle system

Glycerol-3-phosphate dehydrogenases are located both in the cytosol and the intermembrane face of mitochondrial inner membrane. Glycerol 3-phosphate (G3P) and dihydroxyacetone phosphate (DHAP) are so small molecule that they can permeate mitochondrial outer membrane through porins and shuttle between two dehydroganases. Using this shuttle system, NADH generated by cytosolic metabolisms including glycolysis are reoxidized to NAD⁺ reducing DHAP to G3P, and the reducing equivalent can be used for generating proton gradient across the mitochondrial inner membrane by coupling oxidizing G3P and reducing quinone.

Enantiomer

Glycerol 1-phosphate, sometimes called as D-glycerol 3-phosphate, is an enantiomer of glycerol 3-phosphate. Most organisms use 3-phosphate, or L-configuration, for glycerolipid backborn; however, 1-phosphate is specifically used in archeal ether lipids.

Notes