| Purine | |
|---|---|
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| IUPAC name | 7H-purine |
| Identifiers | |
| CAS number | [120-73-0] |
| PubChem | |
| MeSH | |
| SMILES | C1=C2C(=NC=N1)N=CN2 |
| Properties | |
| Molecular formula | C5H4N4 |
| Molar mass | 120. IUPAC Nomenclature is a system of naming Chemical compounds and of describing the science of Chemistry in general CAS registry numbers are unique numerical identifiers for Chemical compounds Polymers biological sequences mixtures and Alloys They are also referred to PubChem is a Database of chemical Molecules The system is maintained by the National Center for Biotechnology Information (NCBI a component Medical Subject Headings ( MeSH) is a huge Controlled vocabulary (or metadata system for the purpose of indexing journal articles and books A chemical formula is a way of expressing information about the Atoms that constitute a particular Chemical compound, and how the relationship between those atoms changes Molar mass, symbol M, is the Mass of one mole of a substance ( Chemical element or Chemical compound) 112 |
| Melting point |
214 °C |
| Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references |
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Purine (1) is a heterocyclic aromatic organic compound, consisting of a pyrimidine ring fused to an imidazole ring. The melting point of a solid is the temperature range at which it changes state from solid to Liquid. In Chemistry, the standard state of a material is its state at 1 bar (100 Kilopascals exactly An organic compound is any member of a large class of Chemical compounds whose Molecules contain Carbon. Pyrimidine is a Heterocyclic Aromatic Organic compound similar to Benzene and Pyridine, containing two Nitrogen Atoms Imidazole is a Organic compound with the formula HC3H3N2 This Aromatic Heterocyclic is classified as an Alkaloid Purines and pyrimidines make up the two groups of nitrogenous bases. Nitrogenous bases are Organic compounds that owe their basic properties to the Lone pair of Electrons of a Nitrogen Atom These bases make up a crucial part of both deoxyribonucleotides and ribonucleotides, and the basis for the universal genetic code.
The general term purines also refers to substituted purines and their tautomers. Tautomers are Organic compounds that are interconvertible by a Chemical reaction called tautomerization.
The purine is the most widely distributed nitrogen-containing heterocycle in nature. [1]
Contents |
Notable purines
The quantity of naturally occurring purines produced on earth is enormous, as 50 % of the bases in nucleic acids, adenine (2) and guanine (3), are purines. A nucleic acid is a Macromolecule composed of chains of monomeric Nucleotides In Biochemistry these Molecules carry Genetic information Adenine is a Purine with a variety of roles in Biochemistry including Cellular respiration, in the form of both the energy-rich Adenosine Guanine is one of the five main Nucleobases found in the Nucleic acids DNA and RNA, the others being Adenine, Cytosine, In DNA, these bases form hydrogen bonds with their complementary pyrimidines thymine and cytosine. Deoxyribonucleic acid ( DNA) is a Nucleic acid that contains the genetic instructions used in the development and functioning of all known A hydrogen bond results from a Dipole-dipole force between an Electronegative atom and a Hydrogen atom bonded to Nitrogen, Oxygen In Molecular biology, complementarity is a property of double-stranded Nucleic acids such as DNA and RNA as well as DNARNA duplexes Pyrimidine is a Heterocyclic Aromatic Organic compound similar to Benzene and Pyridine, containing two Nitrogen Atoms Thymine is one of the four bases in the Nucleic acid of DNA that make up the letters ATGC Cytosine is one of the five main bases found in DNA and RNA. It is a Pyrimidine derivative with a Heterocyclic Aromatic ring This is called complementary base pairing. In RNA, the complement of adenine is uracil (U) instead of thymine. Ribonucleic acid ( RNA) is a Nucleic acid that consists of a long chain of Nucleotide units Uracil is a common and naturally occurring Pyrimidine derivative
Other notable purines are hypoxanthine (4), xanthine (5), theobromine (6), caffeine (7), uric acid (8) and isoguanine (9). Hypoxanthine is a naturally occurring Purine derivative It is occasionally found as a constituent of Nucleic acids where it is present in the Anticodon Xanthine (ˈzænθiːn ˈzænθaɪn] (37-dihydro-purine-26-dione is a Purine base found in most body tissues and fluids and in other organisms Theobromine, also known as xantheose, which also includes the similar compounds Theophylline and Caffeine. Caffeine is a bitter white crystalline Xanthine Alkaloid that acts as a Psychoactive Stimulant Drug and a mild Diuretic Uric acid (or urate) is an Organic compound of Carbon, Nitrogen, Oxygen and Hydrogen with the formula C5H4N4O3 Isoguanine or 2-hydroxyladenine is a Purine base that is an Isomer of Guanine.
Functions
Aside from DNA and RNA, purines are biochemically significant components in a number of other important biomolecules, such as ATP, GTP, cyclic AMP, NADH, and coenzyme A. Adenosine-5'-triphosphate ( ATP) is a multifunctional Nucleotide that is most important as a " molecular currency" of intracellular Energy Guanosine-5'-triphosphate ( GTP) is a Purine Nucleotide. One role is as substrate for the synthesis of RNA during transcription. Cyclic adenosine monophosphate ( cAMP, cyclic AMP or 3'-5'-cyclic Adenosine monophosphate) is a Second messenger that is important in many biological Nicotinamide adenine dinucleotide, abbreviated NAD+, is a Coenzyme found in all living cells The compound is a dinucleotide since it consists Coenzyme A ( CoA, CoASH, or HSCoA) is a Coenzyme, notable for its role in the synthesis and oxidation of Fatty acids Purine (1) itself, has not been found in nature, but it can be produced by organic synthesis. Organic synthesis is a special branch of Chemical synthesis and is concerned with the construction of Organic compounds via Organic reactions Organic
They may also function directly as neurotransmitters, acting upon purinergic receptors. See Chemical synapse for an introduction to concepts and terminology used in this article Purinergic receptors are a family of newly characterized Plasma membrane molecules involved in several and as yet only partially known cellular functions such as vascular reactivity Adenosine, activates adenosine receptors. The adenosine receptors (or P1 receptors) are a class of Purinergic receptors, G-protein coupled receptors with Adenosine as Endogenous
History
The name 'purine' (purum uricum) was coined by the German chemist Emil Fischer in 1884. Germany, officially the Federal Republic of Germany ( ˈbʊndəsʁepuˌbliːk ˈdɔʏtʃlant is a Country in Central Europe. A chemist is a Scientist trained in the Science of Chemistry. Emil Fischer may refer to Emil Fischer (bass (1838-1914 famous German dramatic basso Franz Joseph Emil Fischer (1877-1947 German Year 1884 ( MDCCCLXXXIV) was a Leap year starting on Tuesday (link will display the full calendar of the Gregorian calendar (or a Leap year He synthesized it for the first time in 1899. Year 1899 ( MDCCCXCIX) was a Common year starting on Sunday (link will display the full calendar of the Gregorian calendar (or a Common [2] The starting material for the reaction sequence was uric acid (8), which had been isolated from kidney stones by Scheele in 1776. [3] Uric acid (8) was reacted with PCl5 to give 2,6,8-trichloropurine (10), which was converted with HI and PH4I to give 2,6-diiodopurine (11). A phosphonium salt is a salt containing the Phosphonium (PH4+ ion such as phosphonium iodide (PH4+I&minus This latter product was reduced to purine (1) using zinc-dust.
Metabolism
Many organisms have metabolic pathways to synthesize and break down purines. Many organisms have Metabolic pathways to synthesize and break down Purines Synthesis Purines are biologically synthesized as Nucleotides (bases attached In Biochemistry, a metabolic pathway is a series of chemical reactions occurring within a cell.
Purines are biologically synthesized as nucleosides (bases attached to ribose). See also Adenosine triphosphate (ATP Ribose (ɹˈaɪbəʊs ɹˈaɪbəɹʊs primarily seen as D-ribose, is an Aldopentose — a Monosaccharide containing five Carbon
Food Sources
Purines are found in high concentration in meat and meat products, especially internal organs such as liver and kidney. Plant based diet is generally low in purines [1].
Examples of high purine sources include: sweetbreads, anchovies, sardines, liver, beef, kidneys, brains, meat extracts, herring, mackerel, scallops, game meats, and gravy. Meat extract is highly concentrated Meat stock, usually made from Beef.
A moderate amount of purine is also contained in beef, pork, poultry, fish and seafood, asparagus, cauliflower, spinach, mushrooms, green peas, lentils, dried peas, beans, oatmeal, wheat bran and wheat germ. [4]
Moderate intake of purine-containing food is not associated with an increased risk of gout. Gout (also called metabolic arthritis) is a disease created by a buildup of Uric acid. [5]
Laboratory synthesis
In addition to in vivo synthesis of purines in purine metabolism, purine can also be created artificially. In vivo ( Latin: within the living means that which takes place inside an organism. Many organisms have Metabolic pathways to synthesize and break down Purines Synthesis Purines are biologically synthesized as Nucleotides (bases attached
Purine (1) is obtained in good yield when formamide is heated in an open vessel at 170 oC for 28 hours. [6]
Procedure:[6] Formamide (45 gram) was heated in an open vessel with a condenser for 28 hours in an oil bath at 170-190 oC. After removing excess formamide (32. 1 gram) by vacuum distillation, the residue was refluxed with methanol. The methanol solvent was filtered, the solvent removed from the filtrate by vacuum distillation, and almost pure purine obtained; yield 4. 93 gram (71 % yield from formamide consumed). Crystallization from acetone afforded purine as colorless crystals; melting point 218 oC.
Oro, Orgel and co-workers have shown that four molecules of HCN tetramerize to form diaminomaleodinitrile (12), which can be converted into almost all important natural occurring purines. [7][8][9][10][11]
The Traube purine synthesis (1900) is a classic reaction (named after Wilhelm Traube) between an amine substutited pyrimidine and formic acid [12]
References
- ^ Rosemeyer, H. Wilhelm Traube ( 10 January 1866 &ndash 28 September 1942) was a German Chemist. Amines are Organic compounds and Functional groups that contain a basic Nitrogen Atom with a Lone pair. Pyrimidine is a Heterocyclic Aromatic Organic compound similar to Benzene and Pyridine, containing two Nitrogen Atoms Formic acid (systematically called methanoic acid) is the simplest Carboxylic acid. Chemistry & Biodiversity 2004, 1, 361.
- ^ Fischer, E. Berichte der Deutschen Chemischen Gesellschaft 1899, 32, 2550.
- ^ Scheele, V. Q. Examen Chemicum Calculi Urinari, Opuscula, 1776, 2, 73.
- ^ Gout Diet: Limit High Purine Foods
- ^ NEJM - Purine-Rich Foods, Dairy and Protein Intake, and the Risk of Gout in Men
- ^ a b Yamada, H. ; Okamoto, T. Chemical & Pharmaceutical Bulletin, 1972, 20, 623.
- ^ Sanchez, R. A. ; Ferris, J. P. ; Orgel, L. E. Journal of Molecular Biology, 1967, 30, 223.
- ^ Ferris, J. P. ; Orgel, L. E. Journal of the American Chemical Society, 1966, 88, 1074.
- ^ Ferris, J. P. ; Kuder, J. E. ; Catalano, O. W. Science, 1969, 166, 765.
- ^ Oro, J. ; Kamat, J. S. Nature, 1961, 190, 442.
- ^ Houben-Weyl, Vol . E5, p. 1547
- ^ Organic Syntheses Based on Name Reactions, Alfred Hassner, C. Stumer ISBN 008043259X 2002
See also
External links
Simple aromatic rings, also known as simple arenes or simple aromatics, are Aromatic Organic compounds that consist only of a conjugated Pyrimidine is a Heterocyclic Aromatic Organic compound similar to Benzene and Pyridine, containing two Nitrogen AtomsDapyx Software network: MP3 Explorer | Ebook Manager | Zenithic