Wikipedia:WikiProject Chemicals/Chembox validation/VerifiedDataSandbox and Adenine: Difference between pages

{{Short description|Chemical compound in DNA and RNA}}

{{Distinguish|Adenosine|Adrenaline}}

{{Chembox

| Watchedfields = changed

| verifiedrevid = 477242257

| Name =

| ImageFile =

| ImageFile1 = Adenine.svg

| ImageSize1 = 120px

| ImageFileL2 = Adenine-3D-balls.png

| ImageFileR2 = Adenine-3D-vdW.png

| PIN = 9''H''-Purin-6-amine

| OtherNames = 6-Aminopurine

| SystematicName =

| Section1 = {{Chembox Identifiers

| CASNo = 73-24-5

| CASNo_Ref = {{cascite|correct|CAS}}

| Beilstein = 608603

| ChEBI_Ref = {{ebicite|correct|EBI}}

| ChEBI = 16708

| ChEMBL_Ref = {{ebicite|correct|EBI}}

| ChEMBL = 226345

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID=185

| DrugBank_Ref = {{drugbankcite|correct|drugbank}}

| DrugBank = DB00173

| EINECS = 200-796-1

| Gmelin = 3903

| IUPHAR_ligand = 4788

| PubChem = 190

| RTECS = AU6125000

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = JAC85A2161

| SMILES = NC1=NC=NC2=C1N=CN2

| SMILES1 = Nc1c2ncNc2ncn1

| Section2 = {{Chembox Properties

| C=5 | H=5 | N=5

| MolarMass = 135.13 g/mol

| Appearance = white to light yellow, crystalline

| Density = 1.6 g/cm³ (calculated)

| MeltingPtC = 360 to 365

| MeltingPt_notes = decomposes

| BoilingPt =

| Solubility = 0.103 g/100 mL

| SolubleOther = negligible in [[ethanol]], soluble in hot water and/or [[aqua ammonia]]

| pKa=4.15 (secondary), 9.80 (primary)<ref>Dawson, R.M.C., et al., ''Data for Biochemical Research'', Oxford, Clarendon Press, 1959.</ref>

}}

| Section3 =

| Section4 = {{Chembox Thermochemistry

| DeltaHf = 96.9 kJ/mol

| HeatCapacity = 147.0 J/(K·mol)

| Section5 = {{Chembox Hazards

| ExternalSDS = [http://www.sigmaaldrich.com/MSDS/MSDS/DisplayMSDSPage.do?country=PL&language=EN-generic&productNumber=A8626&brand=SIGMA&PageToGoToURL=http%3A//www.sigmaaldrich.com/catalog/product/sigma/a8626%3Flang%3Dpl MSDS]

| MainHazards =

| FlashPtC=

| AutoignitionPtC =

| LD50 = 227 mg/kg (rat, oral)

| Section6 =

'''Adenine''' ({{IPAc-en|ˈ|æ|d|ᵻ|n|ᵻ|n}}) ([[nucleoside#List of nucleosides and corresponding nucleobases|symbol]] '''A''' or '''Ade''') is a [[purine]] [[nucleotide base]]. It is one of the four nucleobases in the [[nucleic acid]]s of [[DNA]], the other three being [[guanine]] (G), [[cytosine]] (C), and [[thymine]] (T). Adenine derivatives have various roles in [[biochemistry]] including [[cellular respiration]], in the form of both the energy-rich [[adenosine triphosphate]] (ATP) and the [[cofactor (biochemistry)|cofactors]] [[nicotinamide adenine dinucleotide]] (NAD), [[flavin adenine dinucleotide]] (FAD) and [[Coenzyme A]]. It also has functions in [[Protein biosynthesis|protein synthesis]] and as a chemical component of [[DNA]] and [[RNA]].<ref>{{Cite web |title=MedlinePlus: Genetics |url=https://medlineplus.gov/genetics/ |access-date=2022-12-23 |website=medlineplus.gov |language=en}}</ref> The shape of adenine is complementary to either [[thymine]] in [[DNA]] or [[uracil]] in [[RNA]].

The adjacent image shows pure adenine, as an independent molecule. When connected into DNA, a [[covalent bond]] is formed between [[deoxyribose]] sugar and the bottom left nitrogen (thereby removing the existing hydrogen atom). The remaining structure is called an ''adenine residue'', as part of a larger molecule. [[Adenosine]] is adenine reacted with [[ribose]], as used in [[RNA]] and ATP; [[Deoxyadenosine]] is adenine attached to [[deoxyribose]], as used to form DNA.

== Structure ==

[[File:Adenine numbered.svg|thumb|left|150px|Adenine structure, with standard numbering of positions in red.]]

Adenine forms several [[tautomer]]s, 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.<ref>{{Cite journal

|journal =Phys. Chem. Chem. Phys.

|year =2002

|volume =4

|issue =20

|pages =4877–4882

|title =Tautomers and electronic states of jet-cooled adenine investigated by double resonance spectroscopy

|author =Plützer, Chr. |author2=Kleinermanns, K.

|bibcode =2002PCCP....4.4877P

|doi =10.1039/b204595h

}}</ref><ref>{{Cite journal

|title = Experimental matrix isolation and theoretical ab initio HF/6-31G(d, p) studies of infrared spectra of purine, adenine and 2-chloroadenine

|journal = Spectrochimica Acta Part A: Molecular Spectroscopy

|volume = 50

|pages = 1081–1094

|year = 1994

|issn = 0584-8539

|doi = 10.1016/0584-8539(94)80030-8

|author1=M. J. Nowak |author2=H. Rostkowska |author3=L. Lapinski |author4=J. S. Kwiatkowski |author5=J. Leszczynski |issue = 6

|bibcode = 1994AcSpA..50.1081N }}</ref>

== 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 acid]]s [[glycine]], [[glutamine]], and [[aspartic acid]], as well as the coenzyme [[tetrahydrofolate]].

== Manufacturing method ==

Patented Aug. 20, 1968, the current recognized method of industrial-scale production of adenine is a modified form of the formamide method. This method heats up [[formamide]] under 120 degree Celsius conditions within a sealed flask for 5 hours to form adenine. The reaction is heavily increased in quantity by using a phosphorus oxychloride ([[phosphoryl chloride]]) or [[phosphorus pentachloride]] as an acid catalyst and sunlight or ultraviolet conditions. After the 5 hours have passed and the formamide-phosphorus oxychloride-adenine solution cools down, water is put into the flask containing the formamide and now-formed adenine. The water-formamide-adenine solution is then poured through a filtering column of activated charcoal. The water and formamide molecules, being small molecules, will pass through the charcoal and into the waste flask; the large adenine molecules, however, will attach or "adsorb" to the charcoal due to the [[van der Waals force]]s that interact between the adenine and the carbon in the charcoal. Because charcoal has a large surface area, it's able to capture the majority of molecules that pass a certain size (greater than water and formamide) through it. To extract the adenine from the charcoal-adsorbed adenine, ammonia gas dissolved in water ([[Ammonia solution|aqua ammonia]]) is poured onto the activated charcoal-adenine structure to liberate the adenine into the ammonia-water solution. The solution containing water, ammonia, and adenine is then left to air dry, with the adenine losing solubility due to the loss of ammonia gas that previously made the solution basic and capable of dissolving adenine, thus causing it to crystallize into a pure white powder that can be stored.<ref>{{Cite patent|title=Process for preparing adenine|gdate=1966-11-10|url=https://patents.google.com/patent/US3398149A/en}}</ref>

== Function ==

Adenine is one of the two purine [[nucleobase]]s (the other being [[guanine]]) used in forming [[nucleotide]]s of the [[nucleic acid]]s. In DNA, adenine binds to [[thymine]] via two [[hydrogen bond]]s to assist in stabilizing the nucleic acid structures. In RNA, which is used for [[Protein biosynthesis|protein synthesis]], adenine binds to [[uracil]].

{| class="wikitable left" style="text-align:center"

|-

| [[File:Base pair AT.svg|200px]]

| [[File:Base pair AU.svg|200px]]

| [[File:Base pair AD.svg|200px]]

| [[File:Base pair APsi.svg|200px]]

|-

| A-T-Base-pair (DNA)

| A-U-Base-pair (RNA)

| A-D-Base-pair (RNA)

| A-Ψ-Base-pair (RNA)

|}

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 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]]. 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]]

| [[File:Desoxyadenosin.svg|170px]]

|-

| Adenosine, A

| Deoxyadenosine, dA

|}

== History ==

[[File:Template from Crick and Watson’s DNA molecular model, 1953. (9660573227).jpg|thumb|Adenine on Crick and Watson's DNA molecular model, 1953. The picture is shown upside down compared to most modern drawings of adenine, such as those used in this article.]]

In older literature, adenine was sometimes called '''Vitamin B₄'''.<ref>{{Cite journal | vauthors = Reader V | title = The assay of vitamin B(4) | journal = The Biochemical Journal | volume = 24 | issue = 6 | pages = 1827–31 | year = 1930 | pmid = 16744538 | pmc = 1254803 | doi=10.1042/bj0241827}}</ref> 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 (substance)|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 language|Greek]] ''ἀδήν'' aden "gland", in reference to the pancreas, from which Kossel's sample had been extracted.<ref>{{Cite web|last=texte|first=Deutsche chemische Gesellschaft Auteur du|date=1885-01-01|title=Berichte der Deutschen chemischen Gesellschaft zu Berlin|url=https://gallica.bnf.fr/ark:/12148/bpt6k90702f|access-date=2022-12-23|website=Gallica|language=EN}}</ref><ref>{{Cite web|title=adenine &#124; Etymology, origin and meaning of adenine by etymonline|url=https://www.etymonline.com/word/adenine|access-date=2022-12-23|website=www.etymonline.com|language=en}}</ref>

Experiments performed in 1961 by [[Joan Oró]] have shown that a large quantity of adenine can be synthesized from the [[polymerization]] of [[ammonia]] with five [[hydrogen cyanide]] (HCN) molecules in aqueous solution;<ref>{{Cite journal | vauthors = Oro J, Kimball AP | title = Synthesis of purines under possible primitive earth conditions. I. Adenine from hydrogen cyanide | journal = Archives of Biochemistry and Biophysics | volume = 94 | issue = 2 | pages = 217–27 | date = August 1961 | pmid = 13731263 | doi = 10.1016/0003-9861(61)90033-9 }}</ref> whether this has implications for the [[origin of life]] on [[Earth]] is under debate.<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

|pmid =11536683

|pages =83–98

|volume =25

|issue =1–3

|bibcode = 1995OLEB...25...83S |s2cid =21941930

}}</ref>

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]].<ref name="Callahan">{{Cite journal | vauthors = Callahan MP, Smith KE, Cleaves HJ, Ruzicka J, Stern JC, Glavin DP, House CH, Dworkin JP | title = Carbonaceous meteorites contain a wide range of extraterrestrial nucleobases | journal = Proceedings of the National Academy of Sciences of the United States of America | volume = 108 | issue = 34 | pages = 13995–8 | date = Aug 2011 | pmid = 21836052 | doi = 10.1073/pnas.1106493108 | pmc=3161613| bibcode = 2011PNAS..10813995C | doi-access = free }}</ref><ref name="Steigerwald">{{Cite web |last=Steigerwald |first=John |title=NASA Researchers: DNA Building Blocks Can Be Made in Space |url=http://www.nasa.gov/topics/solarsystem/features/dna-meteorites.html |publisher=[[NASA]] |date=8 August 2011 |access-date=2011-08-10 |archive-date=2015-06-23 |archive-url=https://web.archive.org/web/20150623004556/http://www.nasa.gov/topics/solarsystem/features/dna-meteorites.html |url-status=dead }}</ref><ref name="DNA">{{Cite web |author =ScienceDaily Staff |title=DNA Building Blocks Can Be Made in Space, NASA Evidence Suggests|url=https://www.sciencedaily.com/releases/2011/08/110808220659.htm |date=9 August 2011 |website=[[ScienceDaily]] |access-date=2011-08-09}}</ref> 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 [[ultraviolet light|UV light]] is much more complicated than previously thought"; these findings have implications for [[spectroscopy|spectroscopic]] measurements of [[heterocyclic]] compounds, according to one report.<ref name=twsA35>{{Cite web | first1 = Philip | last1 = Williams | name-list-style = vanc | title= Physicists Uncover New Data On Adenine, a Crucial Building Block of Life | website= Science Daily | date = August 18, 2011 | url = https://www.sciencedaily.com/releases/2011/08/110818101731.htm | access-date = 2011-09-01}}

*{{Cite journal |vauthors=[[Mario Barbatti|Barbatti M]], Ullrich S |title=Ionization potentials of adenine along the internal conversion pathways |journal=Physical Chemistry Chemical Physics |date=2011 |volume=13 |issue=34 |pages=15492–15900 |doi=10.1039/C1CP21350D|pmid=21804965 |bibcode=2011PCCP...1315492B }}</ref>

== References ==

{{Reflist}}

== External links ==

{{Commons category|Adenine}}

* [http://gmd.mpimp-golm.mpg.de/Spectrums/f082d045-7938-4e4e-8841-1d748bccc768.aspx Vitamin B4 MS Spectrum]

{{Nucleobases, nucleosides, and nucleotides}}

{{Vitamin}}

{{Authority control}}

[[Category:Nucleobases]]

[[Category:Purines]]

[[Category:Vitamins]]