Adenine
38571
226028406
2008-07-16T14:38:31Z
129.98.104.103
/* Biosynthesis */
{{ For|the programming language Adenine|Adenine (programming language)}}
{{NatOrganicBox
| image= [[Image:Adenine chemical structure.png|116px]] [[Image:Adenine-3d.png|150px]]
| name=9H-purin-6-amine
| synonyms=6-aminopurine
| CAS=73-24-5
| EINECS=200-796-1
| PubChem=190
| C=5 | H=5 | N=5
| mass=135.127
| melt_point=360 - 365
| SMILES=Nc1ncnc2[nH]cnc12
}}
'''Adenine''' is a [[purine]] with a variety of roles in [[biochemistry]] including [[cellular respiration]], in the form of both the energy-rich [[adenosine triphosphate]] (ATP) and the [[cofactor (biochemistry)|cofactor]]s [[nicotinamide adenine dinucleotide]] (NAD) and flavin adenine dinucleotide ([[FAD]]), and [[Protein biosynthesis|protein synthesis]], as a chemical component of [[DNA]] and [[RNA]].<ref>[http://ghr.nlm.nih.gov/ghr/glossary/adenine Definition of Adenine from the Genetics Home Reference] - [[National Institutes of Health]]</ref>
==Structure==
It forms several [[tautomers]], compounds that can be rapidly interconverted and are often considered equivalent.
==Biosynthesis==
The [[Purine metabolism]] involves the formation of Adenine and [[Guanine]]. Both adenine and guanine are derived from the nucleotide inosine monophosphate (IMP), which is synthesised on a pre-existing ribose through a complex pathway using atoms from the amino acids glycine, glutamine, and aspartic acid, as well as formate ions transferred from the coenzyme tetrahydrofolate.
==Function==
Adenine is one of the two purine [[nucleobase]]s used in forming [[nucleotide]]s of the [[nucleic acid]]s. In DNA, adenine binds to [[thymine]] via two [[hydrogen bonds]] to assist in stabilizing the nucleic acid structures. In RNA, which is used in the [[cytoplasm]] for [[Protein biosynthesis|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 [[nucleotide]], when three [[phosphate group]]s are added to adenosine. Adenosine triphosphate is used in cellular metabolism as one of the basic methods of transferring [[chemical energy]] between [[chemical reactions]].
==History==
In older literature, adenine was sometimes called '''Vitamin B<small>4</small>'''.<ref>{{cite journal
|journal=Biochem J.
|year=1930
|volume=24
|issue=6
|pages=1827–31.
|title=The assay of vitamin B4
|author=Vera Reader
|doi=10.1007/BF01581575
}}</ref> It is no longer considered a true vitamin or 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 [[FAD|flavin adenine dinucleotide]] (FAD), respectively.
Some think that, at the [[origin of life]] on [[Earth]], the first adenine was formed by the [[polymerization]] of five [[hydrogen cyanide]] (HCN) molecules.{{Fact|date=May 2008}} However, this has been criticized by some chemists.<ref>{{cite journal
|title=The prebiotic role of adenine: A critical analysis
|first=Robert
|last=Shapiro
|journal=Origins of Life and Evolution of Biospheres
|date=June, [[1995]]
|doi=10.1007/BF01581575
|pages=83–98
|volume=25
|url=http://www.springerlink.com/content/ru56122875200030/}}</ref>
==External links==
* [http://www.compchemwiki.org/index.php?title=Adenine Computational Chemistry Wiki]
==References==
{{reflist}}
{{Nucleobases, nucleosides, and nucleotides}}
{{Vitamin}}
[[Category:Purines]]
[[Category:Vitamins]]
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