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.
Adenine structure, with standard numbering of positions in red.
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.[3][4]
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 forces 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 (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.[5]
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.[6] 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 Greekἀδήν aden "gland", in reference to the pancreas, from which Kossel's sample had been extracted.[7][8]
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;[9] whether this has implications for the origin of life on Earth is under debate.[10]
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.[11][12][13] 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.[14]
ReferencesEdit
^Dawson, R.M.C., et al., Data for Biochemical Research, Oxford, Clarendon Press, 1959.
^Plützer, Chr.; Kleinermanns, K. (2002). "Tautomers and electronic states of jet-cooled adenine investigated by double resonance spectroscopy". Phys. Chem. Chem. Phys. 4 (20): 4877–4882. Bibcode:2002PCCP....4.4877P. doi:10.1039/b204595h.
^M. J. Nowak; H. Rostkowska; L. Lapinski; J. S. Kwiatkowski; J. Leszczynski (1994). "Experimental matrix isolation and theoretical ab initio HF/6-31G(d, p) studies of infrared spectra of purine, adenine and 2-chloroadenine". Spectrochimica Acta Part A: Molecular Spectroscopy. 50 (6): 1081–1094. Bibcode:1994AcSpA..50.1081N. doi:10.1016/0584-8539(94)80030-8. ISSN 0584-8539.
^[1], "Process for preparing adenine", issued 1966-11-10
^Reader V (1930). "The assay of vitamin B(4)". The Biochemical Journal. 24 (6): 1827–31. doi:10.1042/bj0241827. PMC1254803. PMID 16744538.
^texte, Deutsche chemische Gesellschaft Auteur du (1885-01-01). "Berichte der Deutschen chemischen Gesellschaft zu Berlin". Gallica. Retrieved 2022-12-23.
^"adenine | Etymology, origin and meaning of adenine by etymonline". www.etymonline.com. Retrieved 2022-12-23.
^Oro J, Kimball AP (August 1961). "Synthesis of purines under possible primitive earth conditions. I. Adenine from hydrogen cyanide". Archives of Biochemistry and Biophysics. 94 (2): 217–27. doi:10.1016/0003-9861(61)90033-9. PMID 13731263.
^Shapiro, Robert (June 1995). "The prebiotic role of adenine: A critical analysis". Origins of Life and Evolution of Biospheres. 25 (1–3): 83–98. Bibcode:1995OLEB...25...83S. doi:10.1007/BF01581575. PMID 11536683. S2CID 21941930.
^Callahan MP, Smith KE, Cleaves HJ, Ruzicka J, Stern JC, Glavin DP, House CH, Dworkin JP (Aug 2011). "Carbonaceous meteorites contain a wide range of extraterrestrial nucleobases". Proceedings of the National Academy of Sciences of the United States of America. 108 (34): 13995–8. Bibcode:2011PNAS..10813995C. doi:10.1073/pnas.1106493108. PMC3161613. PMID 21836052.
^Steigerwald, John (8 August 2011). "NASA Researchers: DNA Building Blocks Can Be Made in Space". NASA. Retrieved 2011-08-10.
^ScienceDaily Staff (9 August 2011). "DNA Building Blocks Can Be Made in Space, NASA Evidence Suggests". ScienceDaily. Retrieved 2011-08-09.
^Williams P (August 18, 2011). "Physicists Uncover New Data On Adenine, a Crucial Building Block of Life". Science Daily. Retrieved 2011-09-01.
Barbatti M, Ullrich S (2011). "Ionization potentials of adenine along the internal conversion pathways". Physical Chemistry Chemical Physics. 13 (34): 15492–15900. Bibcode:2011PCCP...1315492B. doi:10.1039/C1CP21350D. PMID 21804965.
External linksEdit
Wikimedia Commons has media related to Adenine.
Vitamin B4 MS Spectrum
October 15, 2023
adenine, confused, with, adenosine, adrenaline, symbol, purine, nucleobase, four, nucleobases, nucleic, acids, other, three, being, guanine, cytosine, thymine, derivatives, have, various, roles, biochemistry, including, cellular, respiration, form, both, energ. Not to be confused with Adenosine or Adrenaline Adenine ˈ ae d ɪ n ɪ n symbol A or Ade is a purine nucleobase It is one of the four nucleobases in the nucleic acids 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 cofactors nicotinamide adenine dinucleotide NAD flavin adenine dinucleotide FAD and Coenzyme A It also has functions in protein synthesis and as a chemical component of DNA and RNA 2 The shape of adenine is complementary to either thymine in DNA or uracil in RNA Adenine NamesPreferred IUPAC name 9H Purin 6 amineOther names 6 AminopurineIdentifiersCAS Number 73 24 5 Y3D model JSmol Interactive imageInteractive imageBeilstein Reference 608603ChEBI CHEBI 16708 YChEMBL ChEMBL226345 YChemSpider 185 YDrugBank DB00173 YECHA InfoCard 100 000 724EC Number 200 796 1Gmelin Reference 3903IUPHAR BPS 4788KEGG D00034 YPubChem CID 190RTECS number AU6125000UNII JAC85A2161 YCompTox Dashboard EPA DTXSID6022557InChI InChI 1S C5H5N5 c6 4 3 5 9 1 7 3 10 2 8 4 h1 2H H3 6 7 8 9 10 YKey GFFGJBXGBJISGV UHFFFAOYSA N YInChI 1 C5H5N5 c6 4 3 5 9 1 7 3 10 2 8 4 h1 2H H3 6 7 8 9 10 Key GFFGJBXGBJISGV UHFFFAOYATSMILES NC1 NC NC2 C1N CN2Nc1c2ncNc2ncn1PropertiesChemical formula C 5H 5N 5Molar mass 135 13 g molAppearance white to light yellow crystallineDensity 1 6 g cm3 calculated Melting point 360 to 365 C 680 to 689 F 633 to 638 K decomposesSolubility in water 0 103 g 100 mLSolubility negligible in ethanol soluble in hot water and or aqua ammoniaAcidity pKa 4 15 secondary 9 80 primary 1 ThermochemistryHeat capacity C 147 0 J K mol Std enthalpy offormation DfH 298 96 9 kJ molHazardsLethal dose or concentration LD LC LD50 median dose 227 mg kg rat oral Safety data sheet SDS MSDSExcept where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa Y verify what is Y N Infobox references 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 Contents 1 Structure 2 Biosynthesis 3 Manufacturing method 4 Function 5 History 6 References 7 External linksStructure Edit nbsp Adenine structure with standard numbering of positions in red 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 3 4 Biosynthesis EditPurine 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 Manufacturing method EditPatented 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 forces 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 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 5 Function EditAdenine 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 nbsp nbsp nbsp nbsp A T Base pair DNA A U Base pair RNA A D Base pair RNA A PS 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 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 nbsp nbsp Adenosine A Deoxyadenosine dAHistory Edit nbsp 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 6 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 ἀdhn aden gland in reference to the pancreas from which Kossel s sample had been extracted 7 8 Experiments performed in 1961 by Joan Oro 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 9 whether this has implications for the origin of life on Earth is under debate 10 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 11 12 13 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 14 References Edit Dawson R M C et al Data for Biochemical Research Oxford Clarendon Press 1959 MedlinePlus Genetics medlineplus gov Retrieved 2022 12 23 Plutzer Chr Kleinermanns K 2002 Tautomers and electronic states of jet cooled adenine investigated by double resonance spectroscopy Phys Chem Chem Phys 4 20 4877 4882 Bibcode 2002PCCP 4 4877P doi 10 1039 b204595h M J Nowak H Rostkowska L Lapinski J S Kwiatkowski J Leszczynski 1994 Experimental matrix isolation and theoretical ab initio HF 6 31G d p studies of infrared spectra of purine adenine and 2 chloroadenine Spectrochimica Acta Part A Molecular Spectroscopy 50 6 1081 1094 Bibcode 1994AcSpA 50 1081N doi 10 1016 0584 8539 94 80030 8 ISSN 0584 8539 1 Process for preparing adenine issued 1966 11 10 Reader V 1930 The assay of vitamin B 4 The Biochemical Journal 24 6 1827 31 doi 10 1042 bj0241827 PMC 1254803 PMID 16744538 texte Deutsche chemische Gesellschaft Auteur du 1885 01 01 Berichte der Deutschen chemischen Gesellschaft zu Berlin Gallica Retrieved 2022 12 23 adenine Etymology origin and meaning of adenine by etymonline www etymonline com Retrieved 2022 12 23 Oro J Kimball AP August 1961 Synthesis of purines under possible primitive earth conditions I Adenine from hydrogen cyanide Archives of Biochemistry and Biophysics 94 2 217 27 doi 10 1016 0003 9861 61 90033 9 PMID 13731263 Shapiro Robert June 1995 The prebiotic role of adenine A critical analysis Origins of Life and Evolution of Biospheres 25 1 3 83 98 Bibcode 1995OLEB 25 83S doi 10 1007 BF01581575 PMID 11536683 S2CID 21941930 Callahan MP Smith KE Cleaves HJ Ruzicka J Stern JC Glavin DP House CH Dworkin JP Aug 2011 Carbonaceous meteorites contain a wide range of extraterrestrial nucleobases Proceedings of the National Academy of Sciences of the United States of America 108 34 13995 8 Bibcode 2011PNAS 10813995C doi 10 1073 pnas 1106493108 PMC 3161613 PMID 21836052 Steigerwald John 8 August 2011 NASA Researchers DNA Building Blocks Can Be Made in Space NASA Retrieved 2011 08 10 ScienceDaily Staff 9 August 2011 DNA Building Blocks Can Be Made in Space NASA Evidence Suggests ScienceDaily Retrieved 2011 08 09 Williams P August 18 2011 Physicists Uncover New Data On Adenine a Crucial Building Block of Life Science Daily Retrieved 2011 09 01 Barbatti M Ullrich S 2011 Ionization potentials of adenine along the internal conversion pathways Physical Chemistry Chemical Physics 13 34 15492 15900 Bibcode 2011PCCP 1315492B doi 10 1039 C1CP21350D PMID 21804965 External links Edit nbsp Wikimedia Commons has media related to Adenine Vitamin B4 MS Spectrum Retrieved from https en wikipedia org w index php title Adenine amp oldid 1171752458, wikipedia, wiki, book, books, library,
