Glycerol 3-phosphate

Glycerol 3-phosphate

IUPAC name 1,2,3-Propanetriol, 1- (dihydrogen phosphate)
Other names Glycerophosphate α-glycerolphosphate
Identifiers
CAS number	57-03-4^Y
PubChem	754
ChemSpider	734^Y
KEGG	C03189^Y
MeSH	glycerol+3-phosphate
ChEBI	CHEBI:14336^Y
ChEMBL	CHEMBL358320^Y
Jmol-3D images	Image 1
SMILES O=P(O)(OCC(O)CO)O
InChI InChI=1S/C3H9O6P/c4-1-3(5)2-9-10(6,7)8/h3-5H,1-2H2,(H2,6,7,8)^Y Key: AWUCVROLDVIAJX-UHFFFAOYSA-N^Y InChI=1/C3H9O6P/c4-1-3(5)2-9-10(6,7)8/h3-5H,1-2H2,(H2,6,7,8) Key: AWUCVROLDVIAJX-UHFFFAOYAM
Properties
Molecular formula	C₃H₉O₆P
Molar mass	172.074
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Glycerol 3-phosphate is an organophosphate derived from the reaction catalysed by glycerol kinase (or ATP:glycerol 3-phosphotransferase) where ATP + glycerol <=> ADP + sn-glycerol 3-phosphate. It is a component of glycerophospholipids. It should not be confused with the similarly named glycerate 3-phosphate or glyceraldehyde 3-phosphate. The L-configuration is the active enantiomer.

Function

Glycerol 3-phosphate is produced from glycerol, the triose sugar backbone of triglycerides and glycerophospholipids, by the enzyme glycerol kinase. Glycerol 3-phosphate may then be converted by dehydrogenation to dihydroxyacetone phosphate (DHAP) by the enzyme glycerol-3-phosphate dehydrogenase. DHAP can then be rearranged into glyceraldehyde 3-phosphate(GA3P) by triose phosphate isomerase(TIM), and feed into glycolysis.

The glycerol 3-phosphate shuttle is used to rapidly regenerate NAD⁺ in brain and skeletal muscle cells of mammals.