Phosphoribosyl pyrophosphate

Phosphoribosyl pyrophosphate
Names
	IUPAC name α-D-Ribofuranose 1′-(trihydrogen diphosphate) 5′-(dihydrogen phosphate)
	Systematic IUPAC name (2R,3R,4S,5R)-3,4-Dihydroxy-5-[(phosphonooxy)methyl]oxolan-2-yl trihydrogen diphosphate
	Other names 5-phospho-α-D-ribose 1-diphosphate; PRPP
Identifiers
CAS Number	7540-64-9 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:17111 ;
ChemSpider	7062 ;
DrugBank	DB01632 ;
MeSH	Phosphoribosyl+pyrophosphate
PubChem CID	7339;
UNII	W5555R4ERG ;
CompTox Dashboard (EPA)	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 Key: PQGCEDQWHSBAJP-TXICZTDVSA-N ; 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). Infobox references

Phosphoribosyl pyrophosphate (PRPP) is a pentose phosphate. It is a biochemical intermediate in the formation of purine nucleotides via inosine-5-monophosphate, as well as in pyrimidine nucleotide formation. Hence it is a building block for DNA and RNA.^[1]^[2]^[3] The vitamins thiamine^[4] and cobalamin,^[5] and the amino acid tryptophan also contain fragments derived from PRPP.^[6] It is formed from ribose 5-phosphate (R5P) by the enzyme ribose-phosphate diphosphokinase:^[7]

Quick Facts Names, Identifiers ...

Close

It plays a role in transferring phospho-ribose groups in several reactions, some of which are salvage pathways:^[8]

More information Enzyme, Reactant ...

Enzyme	Reactant	Product
adenine phosphoribosyltransferase	adenine	AMP^[9]
hypoxanthine-guanine phosphoribosyltransferase	guanine	GMP^[10]
hypoxanthine-guanine phosphoribosyltransferase	hypoxanthine	IMP^[10]
nicotinate phosphoribosyltransferase	nicotinate	nicotinate riboside^[11]
orotate phosphoribosyltransferase	orotate	OMP^[12]
uracil phosphoribosyltransferase	uracil	UMP^[13]
xanthine phosphoribosyltransferase	xanthine	XMP^[14]

Close

In de novo generation of purines, the enzyme amidophosphoribosyltransferase acts upon PRPP to create phosphoribosylamine.^[2] The histidine biosynthesis pathway involves the reaction between PRPP and ATP, which activates the latter to ring cleavage. Carbon atoms from ribose in PRPP form the linear chain and part of the imidazole ring in histidine.^[15]^[16]^[17] The same is true for the biosynthesis of tryptophan, with the first step being N-alkylation of anthranilic acid catalysed by the enzyme anthranilate phosphoribosyltransferase.^[15]^[18]^[19]

Increased PRPP