4-Hydroxy-2,4,5-triaminopyrimidine is an organic compound with the formula . The compound is classified as a

pyrimidine Pyrimidine (; ) is an aromatic, heterocyclic, organic compound similar to pyridine (). One of the three diazines (six-membered heterocyclics with two nitrogen atoms in the ring), it has nitrogen atoms at positions 1 and 3 in the ring. The oth ...

substituted with three amino groups and a hydroxyl group.

Tautomers

The title compound is one of several possible

tautomer In chemistry, tautomers () are structural isomers (constitutional isomers) of chemical compounds that readily interconvert. The chemical reaction interconverting the two is called tautomerization. This conversion commonly results from the reloca ...

s. As established by

X-ray crystallography X-ray crystallography is the experimental science of determining the atomic and molecular structure of a crystal, in which the crystalline structure causes a beam of incident X-rays to Diffraction, diffract in specific directions. By measuring th ...

, the doubly protonated derivative 2,4,5-triamino-1,6-dihydropyrimidin-6-one, which is red-orange, can be obtained as the

sulfate The sulfate or sulphate ion is a polyatomic anion with the empirical formula . Salts, acid derivatives, and peroxides of sulfate are widely used in industry. Sulfates occur widely in everyday life. Sulfates are salts of sulfuric acid and many ...

salt.

Preparation and biosynthetic significance

In historic work, 4-hydroxy-2,4,5-triaminopyrimidine was shown to condense with

formic acid Formic acid (), systematically named methanoic acid, is the simplest carboxylic acid. It has the chemical formula HCOOH and structure . This acid is an important intermediate in chemical synthesis and occurs naturally, most notably in some an ...

to give

guanine Guanine () (symbol G or Gua) is one of the four main nucleotide bases found in the nucleic acids DNA and RNA, the others being adenine, cytosine, and thymine ( uracil in RNA). In DNA, guanine is paired with cytosine. The guanine nucleoside ...

, a nucleic acid found in both

RNA Ribonucleic acid (RNA) is a polymeric molecule that is essential for most biological functions, either by performing the function itself (non-coding RNA) or by forming a template for the production of proteins (messenger RNA). RNA and deoxyrib ...

and

DNA Deoxyribonucleic acid (; DNA) is a polymer composed of two polynucleotide chains that coil around each other to form a double helix. The polymer carries genetic instructions for the development, functioning, growth and reproduction of al ...

(not recognized at the time of its synthesis). Traube et al. had previously made 4-hydroxy-2,4,5-triaminopyrimidine by cyclization of cyanoacetylguanidine. Like most aromatic 1,2-diamines, 4-hydroxy-2,4,5-triaminopyrimidine condenses with

glyoxal Glyoxal is an organic compound with the chemical formula OCHCHO. It is the smallest dialdehyde (a compound with two aldehyde groups). It is a crystalline solid, white at low temperatures and yellow near the melting point (15 °C). The liquid ...

to give a

pterin Pterin is a heterocyclic compound composed of a pteridine ring system, with a " keto group" (a lactam) and an amino group on positions 4 and 2 respectively. It is structurally related to the parent bicyclic heterocycle called pteridine. Pter ...

. The biosynthesis of

riboflavin Riboflavin, also known as vitamin B2, is a vitamin found in food and sold as a dietary supplement. It is essential to the formation of two major coenzymes, flavin mononucleotide and flavin adenine dinucleotide. These coenzymes are involved in ...

proceeds via this diamine, which is derived from guanine. 4-Hydroxy-2,4,5-triaminopyrimidine can be prepared in the laboratory from simple precursors that may be relevant to the

origin of life Abiogenesis is the natural process by which life arises from abiotic component, non-living matter, such as simple organic compounds. The prevailing scientific hypothesis is that the transition from non-living to organism, living entities on ...

. Reminiscent of the early work of Traube et al., it arises by

condensation Condensation is the change of the state of matter from the gas phase into the liquid phase, and is the reverse of vaporization. The word most often refers to the water cycle. It can also be defined as the change in the state of water vapor ...

guanidine Guanidine is the compound with the formula HNC(NH2)2. It is a colourless solid that dissolves in polar solvents. It is a strong base that is used in the production of plastics and explosives. It is found in urine predominantly in patients experi ...

aminomalononitrile Aminomalononitrile (AMN) is the organic compound with the formula . The compound can be viewed as an amine-substituted malononitrile. It is of some interest to the study of the chemical origin of life because it represents a trimer of HCN, specu ...

(trimer of HCN), and aminocyanoacetamide.

References

{{DEFAULTSORT:Hydroxy-2,4,5-triaminopyrimidine, 4- Biomolecules Pyrimidines Aromatic bases Simple aromatic rings Substances discovered in the 19th century