Adenine

Structure

Adenine forms several tautomers, compounds that can be rapidly interconverted and are often considered equivalent. However, in isolated conditions, i.e. in an inert gas matrix and in the gas phase, mainly the 9H-adenine tautomer is found.{{Cite journal

Biosynthesis

Purine metabolism involves the formation of adenine and guanine. Both adenine and guanine are derived from the nucleotide inosine monophosphate (IMP), which in turn is synthesized from a pre-existing ribose phosphate through a complex pathway using atoms from the amino acids glycine, glutamine, and aspartic acid, as well as the coenzyme tetrahydrofolate.

Patented August 20, 1968, the current recognized method of industrial-scale production of adenine involves heating formamide under 120 °C.

Function

Adenine is one of the two purine nucleobases (the other being guanine) used in forming nucleotides of the nucleic acids. In DNA, adenine binds to thymine via two hydrogen bonds to assist in stabilizing the nucleic acid structures. In RNA, which is used for protein synthesis, adenine binds to uracil.

Adenine forms adenosine, a nucleoside, when attached to ribose, and deoxyadenosine when attached to deoxyribose. It forms adenosine triphosphate (ATP), a nucleoside triphosphate, when three phosphate groups are added to adenosine. Adenosine triphosphate is used in cellular metabolism as one of the basic methods of transferring chemical energy between chemical reactions. ATP is thus a derivative of adenine, adenosine, cyclic adenosine monophosphate, and adenosine diphosphate.

:{| class="wikitable left" style="text-align:center" |- | [[File:Adenosin.svg|170px|class=skin-invert-image]] | [[File:Desoxyadenosin.svg|170px|class=skin-invert-image]] |- | Adenosine, A | Deoxyadenosine, dA |}

History

In older literature, adenine was sometimes called Vitamin B4, but is no longer considered a vitamin. Due to it being synthesized by the body and not essential to be obtained by diet, it does not meet the definition of vitamin and is no longer part of the Vitamin B complex. However, two B vitamins, niacin and riboflavin, bind with adenine to form the essential cofactors nicotinamide adenine dinucleotide (NAD) and flavin adenine dinucleotide (FAD), respectively. Hermann Emil Fischer was one of the early scientists to study adenine.

It was named in 1885 by Albrecht Kossel after Greek ἀδήν aden "gland", in reference to the pancreas, from which Kossel's sample had been extracted.

Adenine can be prepared from ammonia and hydrogen cyanide (HCN) in aqueous solution, a process that has implications for the origin of life on Earth.{{Cite journal

On August 8, 2011, a report, based on NASA studies with meteorites found on Earth, was published suggesting building blocks of DNA and RNA (adenine, guanine and related organic molecules) may have been formed extraterrestrially in outer space. In 2011, physicists reported that adenine has an "unexpectedly variable range of ionization energies along its reaction pathways" which suggested that "understanding experimental data on how adenine survives exposure to UV light is much more complicated than previously thought"; these findings have implications for spectroscopic measurements of heterocyclic compounds, according to one report.

Notes

References

References

1. Dawson, R.M.C., et al., ''Data for Biochemical Research'', Oxford, Clarendon Press, 1959.
2. Lawrence, Eleanor. "A".
3. Myers, Richard L.. (2007). "The 100 Most Important Chemical Compounds: A Reference Guide". ABC-CLIO.
4. (2023). "Physiology, Adenosine Triphosphate". StatPearls Publishing.
5. "Process for preparing adenine".
6. (1930). "The assay of vitamin B(4)". The Biochemical Journal.
7. texte, Deutsche chemische Gesellschaft Auteur du. (1885-01-01). "Berichte der Deutschen chemischen Gesellschaft zu Berlin".
8. "adenine | Etymology, origin and meaning of adenine by etymonline".
9. (August 1961). "Synthesis of purines under possible primitive earth conditions. I. Adenine from hydrogen cyanide". Archives of Biochemistry and Biophysics.
10. (Aug 2011). "Carbonaceous meteorites contain a wide range of extraterrestrial nucleobases". Proceedings of the National Academy of Sciences of the United States of America.
11. Steigerwald, John. (8 August 2011). "NASA Researchers: DNA Building Blocks Can Be Made in Space". [[NASA]].
12. ScienceDaily Staff. (9 August 2011). "DNA Building Blocks Can Be Made in Space, NASA Evidence Suggests".