4-Hydroxy-2,4,5-triaminopyrimidine

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4-Hydroxy-2,4,5-triaminopyrimidine
TriaminoHydroxopyrimidine.svg
Names
Other names
2,5,6-Triamino-4(1H)-pyrimidinone
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.012.478 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 213-725-4
PubChem CID
UNII
  • InChI=1S/C4H7N5O/c5-1-2(6)8-4(7)9-3(1)10/h5H2,(H5,6,7,8,9,10)
    Key: SYEYEGBZVSWYPK-UHFFFAOYSA-N
  • C1(=C(N=C(NC1=O)N)N)N
Properties
C4H7N5O
Molar mass 141.134 g·mol−1
Melting point 165–167 °C (329–333 °F; 438–440 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

4-Hydroxy-2,4,5-triaminopyrimidine is an organic compound with the formula C4N2(OH)(NH2)3. The compound is classified as a pyrimidine substituted with three amino groups and a hydroxyl group.

Contents

Tautomers

The title compound is one of several possible tautomers. As established by X-ray crystallography, the doubly protonated derivative 2,4,5-triamino-1,6-dihydropyrimidin-6-one, which is red-orange, can be obtained as the sulfate salt. [1]

Preparation and biosynthetic significance

In historic work, 4-hydroxy-2,4,5-triaminopyrimidine was shown to condense with formic acid to give guanine, [2] a nucleic acid found in both RNA and DNA (not recognized at the time of its synthesis). Traube et al. had previously made 4-hydroxy-2,4,5-triaminopyrimidine by cyclization of cyanoacetylguanidine. [3]

Like most aromatic 1,2-diamines, 4-hydroxy-2,4,5-triaminopyrimidine condenses with glyoxal to give a pterin.[ citation needed ]

The biosynthesis of riboflavin proceeds via this diamine, which is derived from guanine. [4]

4-Hydroxy-2,4,5-triaminopyrimidine can be prepared in the laboratory from simple precursors that may be relevant to the origin of life. Reminiscent of the early work of Traube et al., it arises by condensation of guanidine, aminomalononitrile (trimer of HCN), and aminocyanoacetamide. [5]

References

  1. ↑ Tapmeyer, Lukas; Prill, Dragica (2019). "6-Amino-2-iminiumyl-4-oxo-1,2,3,4-tetrahydropyrimidin-5-aminium Sulfate Monohydrate". IUCrData. 4 (5). Bibcode:2019IUCrD...490689T. doi: 10.1107/S2414314619006898 .
  2. ↑ Traube, Wilhelm; Schottländer, Friedrich; Goslich, Carl; Peter, Robert; Meyer, F. A.; Schlüter, Heinrich; Steinbach, Wilhelm; Bredow, Karl (1923). "Über Ortho-diamino-pyrimidine und ihre Überführung in Purine" [Concerning 'o-Diaminopyrimidines and its Transformation into Purines']. Justus Liebigs Annalen der Chemie. 432: 266–96. doi:10.1002/jlac.19234320111.
  3. ↑ Traube, Wilhelm (1900). "Ueber eine neue Synthese des Guanins und Xanthins" [About New Syntheses of Guanines and Xanthines]. Berichte der Deutschen Chemischen Gesellschaft. 33: 1371–1383. doi:10.1002/cber.190003301236.
  4. ↑ Bacher, A.; Lingens, F. (1971). "Biosynthesis of Riboflavin. Formation of 6-Hydroxy-2,4,5-triaminopyrimidine in rib 7 Mutants of Saccharomyces cerevisiae". The Journal of Biological Chemistry. 246 (22): 7018–7022. doi: 10.1016/S0021-9258(19)45944-9 . PMID   4942329.
  5. ↑ Becker, Sidney; Thoma, Ines; Deutsch, Amrei; Gehrke, Tim; Mayer, Peter; Zipse, Hendrik; Carell, Thomas (2016). "A high-yielding, strictly regioselective prebiotic purine nucleoside formation pathway". Science. 352 (6287): 833–836. Bibcode:2016Sci...352..833B. doi:10.1126/science.aad2808. PMID   27174989.
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