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16-September-2008 16:15:15 - Adenine For the programming language Adenine, see Adenine programming language. Adenine Systematic IUPAC name 9H-purin-6-amine Synonyms 6-aminopurine Identifiers CAS number 73-24-5 EINECS 200-796-1 PubChem 190 Chemical data Formula C5H5N5 Molar mass 135.127 SMILES Nc1ncnc2nHcnc12 Physical data Melt. point 360 - 365 °C -265 °F Complete data 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 cofactors nicotinamide adenine dinucleotide NAD and flavin adenine dinucleotide FAD, and protein synthesis, as a chemical component of DNA and RNA.1 Contents 1 Structure 2 Biosynthesis 3 Function 4 History 5 External links 6 References 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 nucleobases 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 in the cytoplasm for 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 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. History In older literature, adenine was sometimes called Vitamin B4.2 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 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.citation needed However, this has been criticized by some chemists.3 External links Computational Chemistry Wiki References ^ Definition of Adenine from the Genetics Home Reference - National Institutes of Health ^ Vera Reader 1930. The assay of vitamin B4. Biochem J. 24 6: 1827-31.. doi:10.1007/BF01581575. ^ Shapiro, Robert June, 1995. The prebiotic role of adenine: A critical analysis. Origins of Life and Evolution of Biospheres 25: 83-98. doi:10.1007/BF01581575. v d e Nucleobases, nucleosides, and nucleotides Nucleobases Purine Adenine, Guanine | Pyrimidine Uracil, Thymine, Cytosine Nucleosides/ NB+pentose Ribonucleosides Adenosine | Guanosine | Uridine | Cytidine Deoxyribonucleosides Deoxyadenosine | Deoxyguanosine | Thymidine | Deoxyuridine | Deoxycytidine Nucleotides/ NS+phosphate Ribonucleotide monophosphates AMP, GMP, UMP, CMP | diphosphates ADP, GDP, UDP, CDP | triphosphates ATP, GTP, UTP, CTP Deoxyribonucleotides monophosphates dAMP, dGMP, dUMP, TMP, dCMP | diphosphates dADP, dGDP, TDP, dCDP | triphosphates dATP, dGTP, TTP, dCTP Cyclic cAMP, cGMP, c-di-GMP, cADPR Major families of biochemicals Saccharides | Carbohydrates | Glycosides | | Amino acids | Peptides | Proteins | Glycoproteins | | Lipids | Terpenes | Steroids | Carotenoids Alkaloids | Nucleobases | Nucleic acids | | Enzyme cofactors | Flavonoids | Polyketides | Tetrapyrroles v d e Vitamins A11 Fat soluble A: Retinol - Beta-carotene - Tretinoin - Alpha-carotene D3: 7-Dehydrocholesterol → Previtamin D3 → Cholecalciferol D3 → Calcidiol → Calcitriol active form → Calcitroic acid D2: Ergosterol → Ergocalciferol D2 D analogues: Dihydrotachysterol - Calcipotriol - Tacalcitol E: Tocopherol - Tocotrienol K: Naphthoquinone - Phylloquinone/K1 - Menatetrenone/K2 Water soluble: B vitamins B1 Thiamine - B2 Riboflavin - B3 Niacin, Nicotinamide - B5 Pantothenic acid, Dexpanthenol, Pantethine - B6 Pyridoxine, Pyridoxal phosphate, Pyridoxamine - B7 Biotin - B9 Folic acid, Folinic acid - B12 Cyanocobalamin, Hydroxocobalamin, Methylcobalamin, Cobamamide Water soluble: other C Ascorbic acid - Choline see also enzyme cofactors Retrieved from http://en..org/wiki/Adenine Categories: Purines | VitaminsHidden categories: All articles with statements | Articles with statements since May 2008 Views Article Discussion this page History Personal tools Log in / create account Navigation Main page Contents Featured content Current events Random article Search Go Search Interaction Community portal Recent changes Contact Donate to Help Toolbox What links here Related changes Upload file Special pages Printable version Permanent link Cite this page Languages العربية БългарÑ?ки Català Česky Dansk Deutsch Eesti Ελληνικά Español Esperanto Français Galego Bahasa Indonesia Italiano עברית Lietuvių Magyar Bahasa Melayu Nederlands ‪Norsk bokmÃ¥l‬ Occitan Polski Português РуÑ?Ñ?кий Simple English SlovenÄ?ina SlovenÅ¡Ä?ina СрпÑ?ки / Srpski Srpskohrvatski / СрпÑ?кохрватÑ?ки Suomi Svenska Tiếng Việt Türkçe УкраїнÑ?ька اردو 䏿–‡ This page was last modified on 24 July 2008, at 00:35
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