View source for Chemistry:2-Amino-5-formylamino-6-(5-phospho-D-ribosylamino)pyrimidin-4(3H)-one

{{DISPLAYTITLE:2-Amino-5-formylamino-6-(5-phospho-{{sc|d}}-ribosylamino)pyrimidin-4(3''H'')-one}}
{{Chembox
| Name = 2-Amino-5-formylamino-6-(5-phospho-{{sc|d}}-ribosylamino)pyrimidin-4(3''H'')-one
| ImageFile = 2-amino-5-formylamino-6-(5-phospho-D-ribosylamino)pyrimidin-4(3H)-one.svg
| ImageSize = 300px
| ImageAlt = 
| IUPACName = (1''R'')-1-[(2-Amino-5-formamido-6-oxo-1,6-dihydropyrimidin-4-yl)amino]-1,4-anhydro-<small>D</small>-ribitol 5-(dihydrogen phosphate)
| SystematicName = {(2''R'',3''S'',4''R'',5''R'')-5-[(2-Amino-5-formamido-6-oxo-1,6-dihydropyrimidin-4-yl)amino]-3,4-dihydroxyoxolan-2-yl}methyl dihydrogen phosphate
| OtherNames = 2-Amino-5-formylamino-6-''ribo''-furanosylamino-4(3''H'')-pyrimidinone monophosphate; 2-Amino-5-formylamino-6-hydroxy-4-(5-phosphoribosylamino)pyrimidine
|Section1={{Chembox Identifiers
| CASNo = 88299-87-0
| CASNo_Ref = {{cascite|correct|CAS}}
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = F6V4VP5MUP
| PubChem = 5460646
| SMILES = C([C@@H]1[C@H]([C@H]([C@@H](O1)NC2=C(C(=O)N=C(N2)N)NC=O)O)O)OP(=O)(O)O
|  ChemSpiderID = 4574141
|  InChI = 1/C10H16N5O9P/c11-10-14-7(4(12-2-16)8(19)15-10)13-9-6(18)5(17)3(24-9)1-23-25(20,21)22/h2-3,5-6,9,17-18H,1H2,(H,12,16)(H2,20,21,22)(H4,11,13,14,15,19)/t3-,5-,6-,9-/m1/s1
|  InChIKey = VKMYTDDVUBGBDH-UUOKFMHZBK
|  StdInChI = 1S/C10H16N5O9P/c11-10-14-7(4(12-2-16)8(19)15-10)13-9-6(18)5(17)3(24-9)1-23-25(20,21)22/h2-3,5-6,9,17-18H,1H2,(H,12,16)(H2,20,21,22)(H4,11,13,14,15,19)/t3-,5-,6-,9-/m1/s1
|  StdInChIKey = VKMYTDDVUBGBDH-UUOKFMHZSA-N

}}
|Section2={{Chembox Properties
| Formula =
| C=10 | H=16 | N=5 | O=9 | P=1 
| MolarMass = 381.24 g/mol
| Appearance = 
| Density = 
| MeltingPt = 
| BoilingPt = 
| Solubility = 
}}
|Section3={{Chembox Hazards
| MainHazards = 
| FlashPt = 
| AutoignitionPt = 
}}
}}

'''2-Amino-5-formylamino-6-(5-phospho-{{sc|d}}-ribosylamino)pyrimidin-4(3''H'')-one''' is a metabolite in the [[Biology:Riboflavin|riboflavin]] biosynthesis pathway. It is formed from [[Chemistry:Guanosine triphosphate|GTP]] by the enzyme [[Biology:GTP cyclohydrolase IIa|GTP cyclohydrolase IIa]] which catalyzes the hydrolysis of the 8,9 bond in the [[Chemistry:Guanine|guanine]] group and loss of the beta and gamma phosphate groups.<ref>{{cite journal |vauthors=Graham DE, Xu H, White RH | year = 2002 | title = A member of a new class of GTP cyclohydrolases produces formylaminopyrimidine nucleotide monophosphates | journal = Biochemistry  | volume = 41 | pages = 15074&ndash;84  | pmid = 12475257 | doi = 10.1021/bi0268798 | issue = 50 }}</ref> The molecule is deformylated by [[Biology:2-amino-5-formylamino-6-ribosylaminopyrimidin-4(3H)-one 5'-monophosphate deformylase|2-amino-5-formylamino-6-ribosylaminopyrimidin-4(3H)-one 5'-monophosphate deformylase]] as the second step in the [[Biology:Archaea|archaea]]l riboflavin biosynthetic pathway.<ref>{{cite journal | title = 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 |author = Grochowski, L.L. |author2 = Xu, H. |author3 = White, R.H. |journal = Biochemistry |year = 2009 |volume = 48 |issue = 19 |pages = 4181–4188 |pmid = 19309161 |doi=10.1021/bi802341p}}</ref>

==References==
{{reflist}}

{{DEFAULTSORT:Amino-5-formylamino-6-(5-phospho-D-ribosylamino)pyrimidin-4(3H)-one, 2-}}
[[Category:Pyrimidines]]

{{Sourceattribution|2-Amino-5-formylamino-6-(5-phospho-D-ribosylamino)pyrimidin-4(3H)-one}}