Chemistry:2,5-Diamino-6-hydroxy-4-(5-phosphoribosylamino)pyrimidine

2,5-Diamino-6-hydroxy-4-(5-phosphoribosylamino)pyrimidine
Names
	IUPAC name (1R)-1,4-Anhydro-1-[(2,5-diamino-6-oxo-1,6-dihydropyrimidin-4-yl)amino]-D-ribitol 5-(dihydrogen phosphate)
	Systematic IUPAC name {(2R,3S,4R,5R)-5-[(2,5-Diamino-6-oxo-1,6-dihydropyrimidin-4-yl)amino]-3,4-dihydroxyoxolan-2-yl}methyl dihydrogen phosphate
	Other names 2,5-Diamino-6-ribofuranosylamino-4(3H)-pyrimidinone monophosphate; N-(2,5-Diamino-6-hydroxypyrimidin-4-yl)-5-O-phosphono-β-D-ribofuranosylamine
Identifiers
CAS Number	73477-63-1 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:29114; tautomer: CHEBI:59546;
ChemSpider	388579;
KEGG	C01304;
PubChem CID	135398601;
	InChI InChI=1S/C9H16N5O8P/c10-3-6(13-9(11)14-7(3)17)12-8-5(16)4(15)2(22-8)1-21-23(18,19)20/h2,4-5,8,15-16H,1,10H2,(H2,18,19,20)(H4,11,12,13,14,17)/t2-,4-,5-,8-/m1/s1 Key: OCLCLRXKNJCOJD-UMMCILCDSA-N; InChI=1/C9H16N5O8P/c10-3-6(13-9(11)14-7(3)17)12-8-5(16)4(15)2(22-8)1-21-23(18,19)20/h2,4-5,8,15-16H,1,10H2,(H2,18,19,20)(H4,11,12,13,14,17)/t2-,4-,5-,8-/m1/s1 Key: OCLCLRXKNJCOJD-UMMCILCDBC;
	SMILES C([C@@H]1[C@H]([C@H]([C@@H](O1)NC2=C(C(=O)N=C(N2)N)N)O)O)OP(=O)(O)O;
Properties
Chemical formula	C9H16N5O8P
Molar mass	353.23 g/mol
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
	Infobox references

2,5-diamino-6-hydroxy-4-(5-phosphoribosylamino)pyrimidine is a metabolite in the purine metabolism, formed by the hydrolysis of GTP by GTP cyclohydrolase II.^[1] Alternatively two separate enzymes can carry out this reaction, initially GTP cyclohydrolase IIa hydrolyses the 8,9 bond to form 2-Amino-5-formylamino-6-(5-phospho-D-ribosylamino)pyrimidin-4(3H)-one,^[2] followed by de-formylation by 2-amino-5-formylamino-6-ribosylaminopyrimidin-4(3H)-one 5'-monophosphate deformylase.^[3] 2,5-diamino-6-hydroxy-4-(5-phosphoribosylamino)pyrimidine is deaminated by Diaminohydroxyphosphoribosylaminopyrimidine deaminase to form 5-amino-6-(5-phosphoribosylamino)uracil.^[4]

References

↑ "Purification and properties of guanosine triphosphate cyclohydrolase II from Escherichia coli". J. Biol. Chem. 250 (9): 3545–51. 1975. doi:10.1016/S0021-9258(19)41549-4. PMID 235552.
↑ "A member of a new class of GTP cyclohydrolases produces formylaminopyrimidine nucleotide monophosphates". Biochemistry 41 (50): 15074–84. 2002. doi:10.1021/bi0268798. PMID 12475257.
↑ Grochowski, L.L.; Xu, H.; White, R.H. (2009). "An iron(II) dependent formamide hydrolase catalyzes the second step in the archaeal biosynthetic pathway to riboflavin and 7,8-didemethyl-8-hydroxy-5-deazariboflavin". Biochemistry 48 (19): 4181–4188. doi:10.1021/bi802341p. PMID 19309161.
↑ "Presence of Escherichia coli of a deaminase and a reductase involved in biosynthesis of riboflavin". J. Bacteriol. 136 (2): 657–67. 1978. doi:10.1128/JB.136.2.657-667.1978. PMID 30756.

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