Glycerol 3-phosphate

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This article is about R-configulation. For S-configulation, see glycerol 1-phosphate.
sn-Glycerol 3-phosphate
Sn-glycerol 3-phosphate.svg
Names
Preferred IUPAC name
(2R)-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
3D model (JSmol)
3DMet
1723975
ChEBI
ChEMBL
DrugBank
ECHA InfoCard 100.000.279 Edit this at Wikidata
EC Number
  • 200-307-1
KEGG
MeSH Alpha-glycerophosphoric+acid
UNII
  • 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
  • C([C@H](COP(=O)(O)O)O)O
Properties
C3H9O6P
Molar mass 172.073 g·mol−1
Related compounds
Glycerol 1-phosphate
Glycerol 2-phosphate
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 glycerol-3-phosphate, 3-O-phosphonoglycerol, 3-phosphoglycerol;[2] and Gro3P.[3] 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.

DHAP + NAD(P)H + H+ → G1P + NAD(P)+

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

Glycerol + ATP → G3P + 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.

G1P + Acyl-CoA → Lysophosphatidic acid + CoA

Glycerol-1-phosphatase removes the phosphate group of glycerol 3-phosphate to generate glycerol, allowing glycerol fermentation to produce glycerol from glucose through glycolysis pathway. A number of microbes, plants and mammals have been shown to express this enzyme.[3]

G3P + H2O → Glycerol + Pi

Shuttle system[]

Main article: Glycerol 3-phosphate shuttle

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 molecules so small that they can permeate the mitochondrial outer membrane through porins and shuttle between two dehydrogenases. Using this shuttle system, NADH generated by cytosolic metabolisms including glycolysis is reoxidized to NAD+ reducing DHAP to G3P, and the reducing equivalent can be used for generating a proton gradient across the mitochondrial inner membrane by coupling and 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 backbone; however, 1-phosphate is specifically used in archeal ether lipids.

Notes[]

  1. ^ This article uses stereospecific numbering where stereoconfiguration is not explicitly specified.
  2. ^ a b G. P. Moss (ed.). "Nomenclature of Phosphorus-Containing Compounds of Biochemical Importance". Archived from the original on 2016-12-08. Retrieved 2015-05-20.
  3. ^ a b Mugabo Y, Zhao S, Siefried A, et al. (26 January 2016). "Identification of a mammalian glycerol-3-phosphate phosphatase". Proceedings of the National Academy of Sciences of the United States of America. 113 (4): E430–9. doi:10.1073/pnas.1514375113. PMC 4743820. PMID 26755581.
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