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WordNet

a colorless crystalline organic base containing nitrogen; the parent compound of various biologically important substances
any of several bases that are derivatives of purine

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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2013/08/07 05:39:03」(JST)

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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 nitrogenous bases, including the two groups of nucleotide bases. Two of the four deoxyribonucleotides and two of the four ribonucleotides, the respective building-blocks of DNA and RNA, are purines.

Notable purines[edit source | edit]

There are many naturally occurring purines. Two of the five bases in nucleic acids, adenine (2) and guanine (3), are purines. In DNA, these bases form hydrogen bonds with their complementary pyrimidines thymine and cytosine, respectively. This is called complementary base pairing. In RNA, the complement of adenine is uracil instead of thymine.

Other notable purines are hypoxanthine (4), xanthine (5), theobromine (6), caffeine (7), uric acid (8) and isoguanine (9).

Functions[edit source | edit]

Aside from the crucial roles of purines (adenine and guanine) in DNA and RNA, purines are also significant components in a number of other important biomolecules, such as ATP, GTP, cyclic AMP, NADH, and coenzyme A. Purine (1) itself, has not been found in nature, but it can be produced by organic synthesis.

They may also function directly as neurotransmitters, acting upon purinergic receptors. Adenosine activates adenosine receptors.

History[edit source | edit]

The word purine (pure urine)^[2] was coined by the German chemist Emil Fischer in 1884. He synthesized it for the first time in 1899.^[3] The starting material for the reaction sequence was uric acid (8), which had been isolated from kidney stones by Scheele in 1776.^[4] 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). The product was reduced to purine (1) using zinc-dust. Purines are also much larger than pyrimidines.

Metabolism[edit source | edit]

Main article: Purine metabolism

Many organisms have metabolic pathways to synthesize and break down purines.

Purines are biologically synthesized as nucleosides (bases attached to 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.

Sources[edit source | edit]

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 NASA studies with meteorites found on Earth, was published suggesting purine and related organic molecules (including the DNA and RNA components, adenine and guanine) may have been formed extraterrestrially in outer space.^[8]^[9]

Laboratory synthesis[edit source | edit]

In addition to in vivo synthesis of purines in 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 HCN tetramerize to form diaminomaleodinitrile (12), which can be converted into almost all natural-occurring purines.^[12]^[13]^[14]^[15]^[16]

The Traube purine synthesis (1900) is a classic reaction (named after Wilhelm Traube) between an amine-substituted pyrimidine and formic acid.^[17]

References[edit source | edit]

^ Rosemeyer, H. Chemistry & Biodiversity 2004, 1, 361.
^ McGuigan, Hugh (1921). An Introduction To Chemical Pharmacology. P. Blakiston's Sons & Co. p. 283. 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. Retrieved 2011-08-15. Unknown parameter |unused_data= ignored (help)
^ Steigerwald, John (8 August 2011). "NASA Researchers: DNA Building Blocks Can Be Made in Space". NASA. 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.
^ Saladino et al.; Crestini, Claudia; Ciciriello, Fabiana; Costanzo, Giovanna; Mauro, Ernesto (2006). "About a Formamide-Based Origin of Informational Polymers: Syntheses of Nucleobases and Favourable Thermodynamic Niches for Early Polymers". Origins of Life and Evolution of Biospheres 36 (5–6): 523–531. doi:10.1007/s11084-006-9053-2. PMID 17136429.
^ Sanchez, R. A.; Ferris, J. P.; Orgel, L. E. (1967). "Studies in prebiotic synthesis. II. Synthesis of purine precursors and amino acids from aqueous hydrogen cyanide". Journal of Molecular Biology 30 (2): 223–53. PMID 4297187.
^ Ferris, J. P.; Orgel, L. E. (1966). Journal of the American Chemical Society 88 (5): 1074. doi:10.1021/ja00957a050.
^ Ferris, J. P.; Kuder, J. E.; Catalano, O. W.; Kuder; Catalano (1969). "Photochemical Reactions and the Chemical Evolution of Purines and Nicotinamide Derivatives". Science 166 (3906): 765–6. Bibcode:1969Sci...166..765F. doi:10.1126/science.166.3906.765. PMID 4241847.
^ Oro, J.; Kamat, J. S.; Kamat (1961). "Amino-acid Synthesis from Hydrogen Cyanide under Possible Primitive Earth Conditions". Nature 190 (4774): 442–3. Bibcode:1961Natur.190..442O. doi:10.1038/190442a0. PMID 13731262.
^ Houben-Weyl, Vol . E5, p. 1547^{[full citation needed]}
^ Organic Syntheses Based on Name Reactions, Alfred Hassner, C. Stumer ISBN 008043259X2002

External links[edit source | edit]

Purine Content in Food

UpToDate Contents

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English Journal

Electrochemical evaluation of DNA methylation level based on the stoichiometric relationship between purine and pyrimidine bases.

Wang P, Chen H, Tian J, Dai Z, Zou X.SourceJiangsu Key Laboratory of Green Synthetic Chemistry for Functional Materials, School of Chemistry and Chemical Engineering, Jiangsu Normal University, Xuzhou 221116, PR China. Electronic address: wangpo@jsnu.edu.cn.
Biosensors & bioelectronics.Biosens Bioelectron.2013 Jul 15;45:34-9. doi: 10.1016/j.bios.2013.01.057. Epub 2013 Feb 7.
An efficient electrochemical approach for the evaluation of DNA methylation level was proposed according to the oxidation signal of DNA bases at an overoxidized polypyrrole (PPyox) directed multiwalled carbon nanotubes (MWNTs) film modified glassy carbon electrode (GCE). The PPyox/MWNTs/GCE exhibite
PMID 23454340

Two 6-(propan-2-yl)-4-methyl-morpholine-2,5-diones as new non-purine xanthine oxidase inhibitors and anti-inflammatory agents.

Smelcerovic A, Rangelov M, Smelcerovic Z, Veljkovic A, Cherneva E, Yancheva D, Nikolic GM, Petronijevic Z, Kocic G.SourceDepartment of Pharmacy, Faculty of Medicine, University of Nis, Bulevar Dr. Zorana Djindjica 81, 18000 Nis, Serbia. Electronic address: a.smelcerovic@yahoo.com.
Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association.Food Chem Toxicol.2013 May;55:493-7. doi: 10.1016/j.fct.2013.01.052. Epub 2013 Feb 11.
Two cyclodidepsipeptides, 3-(2-methylpropyl)-6-(propan-2-yl)-4-methyl-morpholine-2,5-dione (1) and 3,6-di(propan-2-yl)-4-methyl-morpholine-2,5-dione (2), were evaluated for inhibitory activity against commercial enzyme xanthine oxidase (XO) in vitro and XO in rat liver homogenate as well as for anti
PMID 23410588

Catechins are not major components responsible for the beneficial effect of Camellia sinensis on the ovarian δ-ALA-D activity inhibited by cadmium.

Soares MB, Izaguirry AP, Vargas LM, Mendez AS, Spiazzi CC, Santos FW.SourceLaboratório de Biotecnologia da Reprodução (Biotech), Campus Uruguaiana, Universidade Federal do Pampa, CEP 97500-970, Uruguaiana, RS, Brazil.
Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association.Food Chem Toxicol.2013 May;55:463-9. doi: 10.1016/j.fct.2013.01.032. Epub 2013 Jan 31.
Cadmium has been associated with a wide spectrum of deleterious effects on the reproductive tissues, including ovary. This investigation evaluated the protective role of Camellia sinensis (green, white and red teas) in the cadmium-induced inhibition of ovarian δ-aminolevulinate dehydratase (δ-ALA-
PMID 23376781

Glycine consumption and mitochondrial serine hydroxymethyltransferase in cancer cells: The heme connection.

di Salvo ML, Contestabile R, Paiardini A, Maras B.SourceDipartimento di Scienze Biochimiche "A. Rossi Fanelli", Sapienza Università di Roma, Piazzale Aldo Moro 5, 00185 Roma, Italy.
Medical hypotheses.Med Hypotheses.2013 May;80(5):633-6. doi: 10.1016/j.mehy.2013.02.008. Epub 2013 Mar 6.
It was recently discovered that glycine consumption is strongly related to the rate of proliferation across cancer cells. This is very intriguing and raises the question of what is the actual role of this amino acid in cancer metabolism. Cancer cells are greedy for glycine. In particular, the mitoch
PMID 23474074

Japanese Journal

低線量γ線照射細胞からのATP放出とその後のプリン受容体活性化を介した細胞内抗酸化物チオレドキシン-1(Trx-1)の誘導 (特集放射線とアンチエイジング)

小島周二,月本光俊
アンチ・エイジング医学 7(5), 686-691, 2011-10
NAID 40019035467

The improvement of riboflavin production in Ashbya gossypii via disparity mutagenesis and DNA microarray analysis

Park Enoch Y,Ito Yoko,Nariyama Masashi,Sugimoto Takashi,Lies Dwiarti,Kato Tatsuya
Applied microbiology and biotechnology 91(5), 1315-1326, 2011-09
… DNA microarray analysis showed that purine and riboflavin biosynthetic pathways were upregulated, while pathways related to carbon source assimilation, energy generation, and glycolysis were downregulated. …
NAID 120003256124

8-Aminoadenosine Enhances Radiation-induced Cell Death in Human Lung Carcinoma A549 Cells

MEIKE Shunsuke,YAMAMORI Tohru,YASUI Hironobu,EITAKI Masato,MATSUDA Akira,INANAMI Osamu
Journal of radiation research 52(4), 456-463, 2011-07-16
… The purine analogue 8-aminoadenosine (8-NH2-Ado) is known to be a transcription inhibitor that has proved very effective in multiple myeloma cell lines and primary indolent leukemia cells. …
NAID 10029122169

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★リンクテーブル★

リンク元	「プリン」
拡張検索	「P2 purinergic receptor」「purinergic」「6-hydroxy purine」「purine nucleotide phosphorylase deficiency」「2,6,8-trihydroxypurine」

「プリン」

Purine
	IUPAC name 9H-purine
Identifiers
CAS number	120-73-0
PubChem	1044
ChemSpider	1015
KEGG	C15587
MeSH	Purine
ChEBI	CHEBI:17258
ChEMBL	CHEMBL302239
Jmol-3D images	Image 1
	SMILES c1c2c(nc[nH]2)ncn1 ;
	InChI InChI=1S/C5H4N4/c1-4-5(8-2-6-1)9-3-7-4/h1-3H,(H,6,7,8,9) ; Key: KDCGOANMDULRCW-UHFFFAOYSA-N InChI=1/C5H4N4/c1-4-5(8-2-6-1)9-3-7-4/h1-3H,(H,6,7,8,9); Key: KDCGOANMDULRCW-UHFFFAOYAO ;
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)
	Infobox references