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]] [[ar:أدينين]] [[bg:Аденин]] [[ca:Adenina]] [[cs:Adenin]] [[da:Adenin]] [[de:Adenin]] [[et:Adeniin]] [[el:Αδενίνη]] [[es:Adenina]] [[eo:Adenino]] [[fr:Adénine]] [[gl:Adenina]] [[hr:Adenin]] [[id:Adenin]] [[it:Adenina]] [[he:אדנין]] [[lt:Adeninas]] [[hu:Adenin]] [[ms:Adenina]] [[nl:Adenine]] [[ja:アデニン]] [[no:Adenin]] [[oc:Adenina]] [[pl:Adenina]] [[pt:Adenina]] [[ru:Аденин]] [[simple:Adenine]] [[sk:Adenín]] [[sl:Adenin]] [[sr:Аденин]] [[sh:Adenin]] [[fi:Adeniini]] [[sv:Adenin]] [[vi:Adenine]] [[tr:Adenin]] [[uk:Аденін]] [[ur:ادینین]] [[zh:腺嘌呤]]