Phosphoribosyl pyrophosphate

Phosphoribosyl pyrophosphate (PRPP) is a pentosephosphate.

Phosphoribosyl pyrophosphate

Names
Other names 5-phospho-alpha-D-ribose 1-diphosphate
Identifiers
CAS Number	7540-64-9^N
3D model (JSmol)	Interactive image
ChEBI	CHEBI:17111^Y
ChemSpider	7062^Y
DrugBank	DB01632^Y
MeSH	Phosphoribosyl+pyrophosphate
PubChem CID	7339
CompTox Dashboard (EPA)	DTXSID40895038 DTXSID50927778, DTXSID40895038
InChI InChI=1S/C5H13O14P3/c6-3-2(1-16-20(8,9)10)17-5(4(3)7)18-22(14,15)19-21(11,12)13/h2-7H,1H2,(H,14,15)(H2,8,9,10)(H2,11,12,13)/t2-,3-,4-,5-/m1/s1^Y Key: PQGCEDQWHSBAJP-TXICZTDVSA-N^Y InChI=1/C5H13O14P3/c6-3-2(1-16-20(8,9)10)17-5(4(3)7)18-22(14,15)19-21(11,12)13/h2-7H,1H2,(H,14,15)(H2,8,9,10)(H2,11,12,13)/t2-,3-,4-,5-/m1/s1 Key: PQGCEDQWHSBAJP-TXICZTDVBW
SMILES O=P(O[C@H]1O[C@@H]([C@@H](O)[C@H]1O)COP(=O)(O)O)(O)OP(=O)(O)O
Properties
Chemical formula	C5H13O14P3
Molar mass	390.07 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is ^YN ?)
Infobox references

It is formed from ribose 5-phosphate by the enzyme ribose-phosphate diphosphokinase.

It plays a role in transferring phospho-ribose groups in several reactions:

Enzyme	Reactant	Product
adenine phosphoribosyltransferase	adenine	AMP
hypoxanthine-guanine phosphoribosyltransferase	guanine	GMP
hypoxanthine-guanine phosphoribosyltransferase	hypoxanthine	IMP
orotate phosphoribosyltransferase	orotate	OMP
uracil phosphoribosyltransferase	uracil	UMP

In de novo generation of purines, the enzyme amidophosphoribosyltransferase acts upon PRPP to create phosphoribosylamine.

Increased PRPP

Increased levels of PRPP is characterized by the overproduction and accumulation of uric acid leading to hyperuricemia and hyperuricosuria. It is one of the causes of gout.

Increased levels of PRPP are present in Lesch–Nyhan Syndrome. Decreased levels of hypoxanthine guanine phosphoribosyl transferase (HGPRT) causes this accumulation, as PRPP is a substrate used by HGPRT during purine salvage.

See also

• Pyrimidine biosynthesis