Glycerol 3-phosphate

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Glycerol-3-phosphate
)
This article is about R-configulation. For S-configulation, see glycerol 1-phosphate.
sn-Glycerol 3-phosphate
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
C3H7O6P
Molar mass 170.057 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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sn-Glycerol 3-phosphate

stereoisomers of the ester of dibasic phosphoric acid (HOPO32-) and glycerol. It is a component of bacterial and eukaryotic glycerophospholipids.[2]
From a historical reason, it is also known as L-glycerol 3-phosphate, D-glycerol 1-phosphate, L-α-glycerophosphoric acid.

Biosynthesis

Glycerol 3-phosphate is synthesized by reducing

amino acids and citric acid cycle intermediates via the glyceroneogenesis
pathway.

DHAP + NAD(P)H + H+ → G1P + NAD(P)+

It is also synthesized by the phosphorylation of glycerol, which is generated by hydrolysis of fats. This esterification is catalyzed by glycerol kinase.

Glycerol + ATP → G3P + ADP

Metabolism and biological function

Glycerophospholipids have three components: fatty acid lipid groups (orange), glycerol backbone (white), and 3-phosphate ester (green)

Glycerol 3-phosphate is a starting material for de novo synthesis of

eukaryotes, it is first acylated on its sn-1 position by an ER- or mitochondrial membrane enzyme, glycerol-3-phosphate O-acyltransferase. A second acyl group is subsequently installed on the sn-2 position making phosphatidic acids
.

G1P + Acyl-CoA → Lysophosphatidic acid + CoA

Glycerol-1-phosphatase catalyzes the hydrolysis of glycerol 3-phosphate to regenerate glycerol, allowing glycerol fermentation to produce glycerol from glucose through glycolysis pathway. A number of organisms express this enzyme.[2]

G3P + H2O → Glycerol + Pi

Shuttle system

Main article:
Glycerol 3-phosphate shuttle

Glycerol-3-phosphate dehydrogenases are located both in the

proton gradient across the mitochondrial inner membrane by coupling and oxidizing G3P and reducing quinone
.

The Glycerol 3-phosphate shuttle is an emergency back-up system to supply neurons' demand of energy.[3]

Dephosphorylation

Main article: Phosphoglycolate phosphatase

Glycerol-3-phosphate was found to be a substrate for the enzyme phosphoglycolate phosphatase (PGP, or G3PP) in mammals in 2015.[2] G3PP activity has subsequently been suggested to have a regulatory role in central metabolism[2] and stress response.[4]

Glycerol 1-phosphate

Glycerol 1-phosphate, sometimes called as D-glycerol 3-phosphate, is the enantiomer of glycerol 3-phosphate. Eukaryotes use the 3-phosphate, or L-configuration, for glycerolipid backbone. The 1-phosphate is specifically found in archeal lipids.[5]

Notes

  1. ^ This article uses stereospecific numbering where stereoconfiguration is not explicitly specified.
  2. ^ Equally appropriate names in biochemical context include glycerol-3-phosphate, 3-O-phosphonoglycerol, 3-phosphoglycerol[1] and Gro3P.
  1. ^ G. P. Moss (ed.). "Nomenclature of Phosphorus-Containing Compounds of Biochemical Importance". Archived from the original on 2016-12-08. Retrieved 2015-05-20.
  2. ^
    PMID 26755581
    .
  3. ^ "Neuronal Back-up System Discovered". August 30, 2022.
  4. PMID 35017476
    .
  5. PMID 28007654
    .
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