2,3-Bisphosphoglyceric acid

2,3-Bisphosphoglyceric acid
Names
	Preferred IUPAC name 2,3-Bis(phosphonooxy)propanoic acid
	Other names 2,3-Diphosphoglyceric acid; 2,3-Diphosphoglycerate; 2,3-Bisphosphoglycerate
Identifiers
CAS Number	138-81-8 ;
3D model (JSmol)	Interactive image;
Abbreviations	2,3-BPG; 2,3-DPG; 23BPG
ChEBI	CHEBI:17720 ;
ChemSpider	161681 ; 60 (Racemic) ;
KEGG	C01159 ;
PubChem CID	61;
UNII	TZ4454O4YZ ;
	InChI InChI=1S/C3H8O10P2/c4-3(5)2(13-15(9,10)11)1-12-14(6,7)8/h2H,1H2,(H,4,5)(H2,6,7,8)(H2,9,10,11)/t2-/m1/s1 Key: XOHUEYCVLUUEJJ-UWTATZPHSA-N ; Key: XOHUEYCVLUUEJJ-UWTATZPHBL;
	SMILES O=P(O)(OC(C(=O)O)COP(=O)(O)O)O;
Properties
Chemical formula	C3H8O10P2
Molar mass	266.035 g·mol−1
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

2,3-Bisphosphoglyceric acid (conjugate base 2,3-bisphosphoglycerate) (2,3-BPG), also known as 2,3-diphosphoglyceric acid (conjugate base 2,3-diphosphoglycerate) (2,3-DPG), is a three-carbon isomer of the glycolytic intermediate 1,3-bisphosphoglyceric acid (1,3-BPG).

D-2,3-BPG is present in human red blood cells (RBC; erythrocyte) at approximately 5 mmol/L. It binds with greater affinity to deoxygenated hemoglobin (e.g., when the red blood cell is near respiring tissue) than it does to oxygenated hemoglobin (e.g., in the lungs) due to conformational differences: 2,3-BPG (with an estimated size of about 9 Å) fits in the deoxygenated hemoglobin conformation (with an 11-Angstrom pocket), but not as well in the oxygenated conformation (5 Angstroms). It interacts with deoxygenated hemoglobin beta subunits and decreases the affinity for oxygen and allosterically promotes the release of the remaining oxygen molecules bound to the hemoglobin. Therefore, it enhances the ability of RBCs to release oxygen near tissues that need it most. 2,3-BPG is thus an allosteric effector.

Its function was discovered in 1967 by Reinhold Benesch and Ruth Benesch.

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