2,5-Diamino-6-hydroxy-4-(5-phosphoribosylamino)pyrimidine
Appearance
(Redirected from 2,5-diamino-6-hydroxy-4-(5-phosphoribosylamino)pyrimidine)
Names | |
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IUPAC name
(1R)-1,4-Anhydro-1-[(2,5-diamino-6-oxo-1,6-dihydropyrimidin-4-yl)amino]-D-ribitol 5-(dihydrogen phosphate)
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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
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Identifiers | |
3D model (JSmol)
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ChEBI |
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KEGG | |
PubChem CID
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CompTox Dashboard (EPA)
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Properties | |
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).
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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
[edit]- ^ Foor F, Brown GM (1975). "Purification and properties of guanosine triphosphate cyclohydrolase II from Escherichia coli". J. Biol. Chem. 250 (9): 3545–51. doi:10.1016/S0021-9258(19)41549-4. PMID 235552.
- ^ 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.
- ^ 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.
- ^ Burrows RB, Brown GM (1978). "Presence of Escherichia coli of a deaminase and a reductase involved in biosynthesis of riboflavin". J. Bacteriol. 136 (2): 657–67. doi:10.1128/JB.136.2.657-667.1978. PMC 218591. PMID 30756.