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

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2,5-Diamino-6-hydroxy-4-(5-phosphoribosylamino)pyrimidine
Names
IUPAC name (1R)-1,4-Anhydro-1--D-ribitol 5-(dihydrogen phosphate)
Systematic IUPAC name {(2R,3S,4R,5R)-5--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
3D model (JSmol)
ChEBI
ChemSpider
KEGG
PubChem CID
CompTox Dashboard (EPA)
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/s1Key: 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/s1Key: OCLCLRXKNJCOJD-UMMCILCDBC
SMILES
  • C(1(((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 , 100 kPa). Infobox references
Chemical compound

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. 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, followed by de-formylation by 2-amino-5-formylamino-6-ribosylaminopyrimidin-4(3H)-one 5'-monophosphate deformylase. 2,5-diamino-6-hydroxy-4-(5-phosphoribosylamino)pyrimidine is deaminated by Diaminohydroxyphosphoribosylaminopyrimidine deaminase to form 5-amino-6-(5-phosphoribosylamino)uracil.

References

  1. 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.
  2. 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.
  3. 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.
  4. 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.


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