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Adenine (symbol A or Ade) is a that is found in , , and ATP.

(2025). 9780313337581, ABC-CLIO. .
Usually a white crystalline subtance. The shape of adenine is complementary and pairs to either in DNA or in RNA. In cells adenine, as an independent molecule, is rare. It is almost always to become a part of a larger biomolecule.

Adenine has a central role in cellular respiration. It is part of adenosine triphosphate which provides the that drives and supports most activities in living cells, such as protein synthesis, chemical synthesis, muscle contraction, and propagation. In respiration it also participates as part of the cofactors nicotinamide adenine dinucleotide, flavin adenine dinucleotide, and .

It is also part of , adenosine monophosphate, cyclic adenosine monophosphate, adenosine diphosphate, and S-adenosylmethionine.


Structure
Adenine forms several , 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.


Biosynthesis
Purine metabolism involves the formation of adenine and . Both adenine and guanine are derived from the nucleotide inosine monophosphate (IMP), which in turn is synthesized from a pre-existing through a complex pathway using atoms from the , , and , as well as the coenzyme .

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


Function
Adenine is one of the two purine (the other being ) used in forming of the . In DNA, adenine binds to via two to assist in stabilizing the nucleic acid structures. In RNA, which is used for protein synthesis, adenine binds to .

A-T-Base-pair (DNA)A-U-Base-pair (RNA)A-D-Base-pair (RNA)A-Ψ-Base-pair (RNA)

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

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Adenosine, ADeoxyadenosine, 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 and is no longer part of the complex. However, two B vitamins, niacin and , 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 after ἀδήν aden "gland", in reference to the pancreas, from which Kossel's sample had been extracted.

Adenine can be prepared from and (HCN) in aqueous solution, a process that has implications for the origin of life on .

On August 8, 2011, a report, based on studies with found on , was published suggesting building blocks of and (adenine, and related organic molecules) may have been formed extraterrestrially in . 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 measurements of compounds, according to one report.


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