Glycerol 2-phosphate

Glycerol 2-phosphate is the conjugate base of phosphoric ester of glycerol. It is commonly known as β-glycerophosphate or BGP. Unlike glycerol 1-phosphate and glycerol 3-phosphate, this isomer is not chiral. It is also less common.

Glycerol 2-phosphate

Names
Preferred IUPAC name 1,3-Dihydroxypropan-2-yl dihydrogen phosphate
Other names 1,2,3-Propanetriol, 2-(dihydrogen phosphate) Glycerol 2-phosphate β-Glycerophosphate β-Phosphoglycerol BGP
Identifiers
CAS Number	17181-54-3
3D model (JSmol)	Interactive image
ChEBI	CHEBI:17270
ChEMBL	ChEMBL1232903
ChemSpider	2431
DrugBank	DB01779
ECHA InfoCard	100.037.465
EC Number	241-228-2
KEGG	C02979
MeSH	Beta-glycerophosphoric+acid
PubChem CID	2526
UNII	WWH06G87W6
CompTox Dashboard (EPA)	DTXSID1023106
InChI InChI=1S/C3H9O6P/c4-1-3(2-5)9-10(6,7)8/h3-5H,1-2H2,(H2,6,7,8) Key: DHCLVCXQIBBOPH-UHFFFAOYSA-N
SMILES C(C(CO)OP(=O)(O)O)O
Properties
Chemical formula	C3H9O6P
Molar mass	172.073 g·mol−1
Appearance	forms colorless salts
Related compounds
Related organophosphates	Glycerol 1-phosphate Glycerol 3-phosphate
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Applications

β-Glycerophosphate is an inhibitor of the enzyme serine/threonine phosphatase. It is often used in combination with other phosphatase/protease inhibitors for broad spectrum inhibition.^[1][2]

Although previously presumed to be non-transportable and reliant on extracellular phosphatases such as alkaline phosphatase (PhoA) for utilization, recent research indicates that Escherichia coli can use β-Glycerophosphate as a sole phosphorus source in the absence of PhoA, relying on the Ugp transporter system encoded by the ugpBAECQ operon.^[3]

β-Glycerophosphate is also used to drive osteogenic differentiation of bone marrow stem cells in vitro.^[4]

β-Glycerophosphate is used to buffer M17 media for Lactococcus culture in recombinant protein expression.^[5]

Formation

Glycerol 2-phosphate (G2P) can be formed through abiotic phosphorylation under prebiotic conditions, as demonstrated in laboratory simulations of early Earth environments.^[6] In the presence of urea and heat, glycerol and phosphate undergo regioselective phosphorylation, favoring the 2-position to yield G2P.^[6] This process suggests a plausible prebiotic pathway for the synthesis of key metabolic intermediates like G2P, which may have contributed to the origin of biological phospholipid synthesis prior to enzymatic catalysis.^[6]