Purine | |
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9H-purine |
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Identifiers | |
CAS number | 120-73-0 |
PubChem | 1044 |
ChemSpider | 1015 |
KEGG | C15587 |
MeSH | Purine |
ChEBI | CHEBI:17258 |
ChEMBL | CHEMBL302239 |
Jmol-3D images | Image 1 |
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Properties | |
Molecular formula | C5H4N4 |
Molar mass | 120.11 g mol?1 |
Melting point |
214 °C, 487 K, 417 °F |
(verify) (what is: / ?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) |
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Infobox references |
A purine is a heterocyclic aromatic organic compound. It consists of a pyrimidine ring fused to an imidazole ring. Purines, including substituted purines and their tautomers, are the most widely occurring nitrogen-containing heterocycle in nature.[1]
Purines and pyrimidines make up the two groups of RNA, are purines.
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[edit] Notable purines
There are many naturally occurring purines. Two of the four bases in uracil instead of thymine.
Other notable purines are isoguanine (9).
[edit] Functions
Aside from the crucial role of purines (adenine and guanine) in DNA and RNA, purines are also significant components in a number of other important biomolecules, such as organic synthesis.
They may also function directly as adenosine receptors.
[edit] History
The word purine (purum uricum)PH4I to give 2,6-diiodopurine (11). The product was reduced to purine (1) using zinc-dust. Purines are also much larger than pyrimidines.
[edit] Metabolism
Many organisms have metabolic pathways to synthesize and break down purines.
Purines are biologically synthesized as ribose).
Defects in enzymes that control purine production and breakdown can severely alter a cell’s DNA sequences, which may explain why people who carry certain genetic variants of purine metabolic enzymes have a higher risk for some types of cancer. [17]
[edit] Sources
Purines are found in high concentration in meat and meat products, especially internal organs such as liver and kidney. In general, plant-based diets are low in purines.[5] Examples of high-purine sources include: sweetbreads, anchovies, sardines, liver, beef kidneys, brains, meat extracts (e.g., Oxo, Bovril), herring, mackerel, scallops, game meats, beer (from the yeast) and gravy.
A moderate amount of purine is also contained in beef, pork, poultry, other fish and seafood, asparagus, cauliflower, spinach, mushrooms, green peas, lentils, dried peas, beans, oatmeal, wheat bran, wheat germ, and hawthorn.[6]
Higher levels of meat and seafood consumption are associated with an increased risk of gout, whereas a higher level of consumption of dairy products is associated with a decreased risk. Moderate intake of purine-rich vegetables or protein is not associated with an increased risk of gout.[7]
In August 2011, a report, based on [9]
[edit] Laboratory synthesis
In addition to purine metabolism, purine can also be created artificially.
Purine (1) is obtained in good yield when formamide is heated in an open vessel at 170 °C for 28 hours.[10]
This remarkable reaction and others like it have been discussed in the context of the origin of life.[11]
Oro, Orgel and co-workers have shown that four molecules of [16]
The Traube purine synthesis (1900) is a classic reaction (named after Wilhelm Traube) between an amine-substituted pyrimidine and formic acid.[17]
[edit] See also
[edit] References
- ^ Rosemeyer, H. Chemistry & Biodiversity 2004, 1, 361.
- http://www.ebooksread.com/authors-eng/hugh-mcguigan/an-introduction-to-chemical-pharmacology-pharmacodynamics-in-relation-to–goo/page-20-an-introduction-to-chemical-pharmacology-pharmacodynamics-in-relation-to–goo.shtml. Retrieved July 18, 2012.
- ^ Fischer, E. Berichte der Deutschen Chemischen Gesellschaft 1899, 32, 2550.
- ^ Scheele, V. Q. Examen Chemicum Calculi Urinari, Opuscula, 1776, 2, 73.
- ^ http://www.dietaryfiberfood.com/purine-food.php
- ^ Gout Diet: Limit High Purine Foods
- ^ NEJM – Purine-Rich Foods, Dairy and Protein Intake, and the Risk of Gout in Men
- ^ Callahan; Smith, K.E.; Cleaves, H.J.; Ruzica, J.; Stern, J.C.; Glavin, D.P.; House, C.H.; Dworkin, J.P. (11 August 2011). “Carbonaceous meteorites contain a wide range of extraterrestrial nucleobases”. PNAS. doi:10.1073/pnas.1106493108. http://www.pnas.org/content/early/2011/08/10/1106493108. Retrieved 2011-08-15.
- ^ Steigerwald, John (8 August 2011). “NASA Researchers: DNA Building Blocks Can Be Made in Space”. NASA. http://www.nasa.gov/topics/solarsystem/features/dna-meteorites.html. Retrieved 2011-08-10.
- ^ Yamada, H.; Okamoto, T. (1972). “A One-step Synthesis of Purine Ring from Formamide”. Chemical & Pharmaceutical Bulletin 20 (3): 623. doi:10.1248/cpb.20.623. http://www.journalarchive.jst.go.jp/english/jnlabstract_en.php?cdjournal=cpb1958&cdvol=20&noissue=3&startpage=623.
- 17136429.
- ^ 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 008043259X2002
[17] Bo Panga, Jose L. McFalinea, Nicholas E. Burgisb, Min Donga, Koli Taghizadehc, Matthew R. Sullivana, C. Eric Elmquista, Richard P. Cunninghamb, and Peter C. Dedona,c,5 PNAS January 30, 2012, http://www.pnas.org/content/early/2012/01/26/1118455109.abstract
[edit] External links
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This article uses material from the Wikipedia article Purine, which is released under the Creative Commons Attribution-Share-Alike License 3.0.