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

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2-Amino-5-formylamino-6-(5-phospho-D-ribosylamino)pyrimidin-4(3H)-one
Names
IUPAC name
(1R)-1-[(2-Amino-5-formamido-6-oxo-1,6-dihydropyrimidin-4-yl)amino]-1,4-anhydro-D-ribitol 5-(dihydrogen phosphate)
Systematic IUPAC name
{(2R,3S,4R,5R)-5-[(2-Amino-5-formamido-6-oxo-1,6-dihydropyrimidin-4-yl)amino]-3,4-dihydroxyoxolan-2-yl}methyl dihydrogen phosphate
Other names
2-Amino-5-formylamino-6-ribo-furanosylamino-4(3H)-pyrimidinone monophosphate; 2-Amino-5-formylamino-6-hydroxy-4-(5-phosphoribosylamino)pyrimidine
Identifiers
3D model (JSmol)
ChemSpider
UNII
  • InChI=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
    Key: VKMYTDDVUBGBDH-UUOKFMHZSA-N
  • 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
    Key: VKMYTDDVUBGBDH-UUOKFMHZBK
  • 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
Properties
C10H16N5O9P
Molar mass 381.24 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

2-Amino-5-formylamino-6-(5-phospho-D-ribosylamino)pyrimidin-4(3H)-one is a metabolite in the riboflavin biosynthesis pathway. It is formed from GTP by the enzyme GTP cyclohydrolase IIa which catalyzes the hydrolysis of the 8,9 bond in the guanine group and loss of the beta and gamma phosphate groups.[1] The molecule is deformylated by 2-amino-5-formylamino-6-ribosylaminopyrimidin-4(3H)-one 5'-monophosphate deformylase as the second step in the archaeal riboflavin biosynthetic pathway.[2]

References

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  1. ^ Graham DE, Xu H, White RH (2002). "A member of a new class of GTP cyclohydrolases produces formylaminopyrimidine nucleotide monophosphates". Biochemistry. 41 (50): 15074–84. doi:10.1021/bi0268798. PMID 12475257.
  2. ^ 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.
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