NationMaster - Encyclopedia: Purine

Purine (1) is a heterocyclic aromatic organic compound, consisting of a pyrimidine ring fused to an imidazole ring. Purines make up one of the two groups of nitrogenous bases. Pyrimidines make up the other group. These bases make up a crucial part of both deoxyribonucleotides and ribonucleotides, and the basis for the universal genetic code. The plimsoll symbol as used in shipping In chemistry, the standard state of a material is its state at 1 bar (100 kilopascals exactly). ... Heterocyclic compounds are substances which contain a ring structure as found in benzene and the aromatic compounds, or aromatic hydrocarbons, but in which other atoms than carbon, such as sulfur, oxygen or nitrogen are found as part of the ring. ... In chemistry, an aromatic molecule is one in which electrons are free to cycle around circular arrangements of atoms, which are alternately singly and doubly bonded to one another. ... Benzene is the simplest of the arenes, a family of organic compounds 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 at positions 1 and 3 of the six-member ring [1]. It is isomeric with two other forms of diazine. ... Imidazole is a heterocyclic aromatic organic compound. ... Pyrimidine is a heterocyclic aromatic organic compound similar to benzene and pyridine, containing two nitrogen atoms at positions 1 and 3 of the six-member ring [1]. It is isomeric with two other forms of diazine. ...

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] Heterocycles are organic chemical structures containing non-carbon elements. ...

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. In DNA, these bases form hydrogen bonds with their complementary pyrimidines thymine and cytosine. This is called complementary base pairing. In RNA, the complement of adenine is uracil (U) instead of thymine. Look up nucleic acid in Wiktionary, the free dictionary. ... For the programming language Adenine, see Adenine (programming language). ... Guanine is one of the five main nucleobases found in the nucleic acids DNA and RNA; the others being adenine, cytosine, thymine, and uracil. ... The structure of part of a DNA double helix Deoxyribonucleic acid, or DNA, is a nucleic acid molecule that contains the genetic instructions used in the development and functioning of all known living organisms. ... An example of a quadruple hydrogen bond between a self-assembled dimer complex reported by Meijer and coworkers. ... On the left: nucleotides that forms the DNA and their complementary. ... Pyrimidine is a heterocyclic aromatic organic compound similar to benzene and pyridine, containing two nitrogen atoms at positions 1 and 3 of the six-member ring [1]. It is isomeric with two other forms of diazine. ... For the similarly-spelled vitamin compound, see Thiamine Thymine, also known as 5-methyluracil, is a pyrimidine nucleobase. ... Cytosine is one of the 5 main nucleobases used in storing and transporting genetic information within a cell in the nucleic acids DNA and RNA. It is a pyrimidine derivative, with a heterocyclic aromatic ring and two substituents attached (an amine group at position 4 and a keto group at... For other uses, see RNA (disambiguation). ... Uracil is a pyrimidine which is common and naturally occurring. ...

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, and one of the products of the action of xanthine oxidase on xanthine, though more normally in purine degradation, hypoxanthine is oxidized by xanthine oxidase to form xanthine. ... Xanthines are a group of alkaloids that are commonly used for their effects as mild stimulants and as bronchodilators, notably in treating the symptoms of asthma. ... Theobromine, also known as xantheose,[1] is a bitter alkaloid of the cacao plant. ... Caffeine is a xanthine alkaloid compound that acts as a stimulant in humans. ... 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. Purine (1) itself, has not been found in nature, but it can be produced by organic synthesis. Adenosine 5-triphosphate (ATP) is a multifunctional nucleotide that is most important as a molecular currency of intracellular energy transfer. ... Guanosine triphosphate (GTP) is also known as guanosine-5-triphosphate. ... Structure of cAMP Cyclic adenosine monophosphate (cAMP, cyclic AMP or 3-5-cyclic adenosine monophosphate) is a molecule that is important in many biological processes; it is derived from adenosine triphosphate (ATP). ... Nicotinamide adenine dinucleotide (NAD+) Nicotinamide adenine dinucleotide (NAD) and nicotinamide adenine dinucleotide phosphate (NADP) are two important coenzymes found in cells. ... Coenzyme A (CoA, CoASH, or HSCoA) is a coenzyme, notable for its role in the synthesis and oxidization of fatty acids, and the oxidation of pyruvate in the citric acid cycle. ... Organic synthesis is the construction of organic molecules via chemical processes. ...

They may also function directly as neurotransmitters, acting upon purinergic receptors. Adenosine, activates adenosine receptors. Neurotransmitters are chemicals that are used to relay, amplify and modulate electrical signals between a presynaptic and a postsynaptic neuron. ... Purinergic receptors are a family of receptors which are activated by purine-containing compounds such as adenosine and the nucleotides ATP and UTP. The members of the family include the following: Adenosine receptor MeSH Purinergic+Receptors Transmembrane receptor: G protein-coupled receptors Adenosine - Adrenergic - Angiotensin - Bradykinin - Calcitonin - Cannabinoid - Chemokine - Cholecystokinin... To meet Wikipedias quality standards, this article or section may require cleanup. ...

History

The name 'purine' (purum uricum) was coined by the German chemist Emil Fischer in 1884. He synthesized it for the first time in 1899.^[2] The starting material for the reaction sequence was uric acid (8), which had been isolated from gallstones 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). This latter product was reduced to purine (1) using zinc-dust. A chemist pours from a round-bottom flask. ... Hermann Emil Fischer (October 9, 1852 - July 15, 1919) was a German chemist and recipient of the Nobel Prize for Chemistry in 1902. ... Year 1884 (MDCCCLXXXIV) was a leap year starting on Tuesday (link will display the full calendar) of the Gregorian calendar (or a leap year starting on Sunday of the 12-day-slower Julian calendar). ... Year 1899 (MDCCCXCIX) was a common year starting on Sunday (link will display the full calendar) of the Gregorian calendar (or a common year starting on Friday [1] of the 12-day-slower Julian calendar). ...

Metabolism

Many organisms have metabolic pathways to synthesize and break down purines. Many organisms have metabolic pathways to synthesise and break down purines. ... 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). Nucleosides are glycosylamines made by attaching a nucleobase (often reffered to simply as bases) to a ribose ring. ... Ribose Ribose, primarily seen as D-ribose, is an aldopentose â€” a monosaccharide containing five carbon atoms, and including an aldehyde functional group. ...

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 [3].

Examples of high purine sources include: sweetbreads, anchovies, sardines, liver, beef kidneys, brains, meat extracts (e.g Oxo, Bovril), herring, mackerel, scallops, game meats, and gravy.

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.^[5]

Synthesis

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]

References

See also

Simple aromatic rings are aromatic organic compounds (also known as arenes or aromatics) that consist only of conjugated planar ring systems with delocalized pi electron clouds instead of discrete alternating single and double bonds. ... Pyrimidine is a heterocyclic aromatic organic compound similar to benzene and pyridine, containing two nitrogen atoms at positions 1 and 3 of the six-member ring [1]. It is isomeric with two other forms of diazine. ...

External links

Categories: Purines | Amines | Nitrogen heterocycles | Aromatic compounds | Heterocyclic compounds | Simple aromatic rings | Aromatic bases Biochemistry (from Greek: , bios, life and Egyptian kÄ“me, earth[1]) is the study of the chemical processes in living organisms. ... Peptides (from the Greek Ï€ÎµÏ€Ï„Î¿Ï‚, digestible), are the family of short molecules formed from the linking, in a defined order, of various Î±-amino acids. ... This article is about the class of chemicals. ... Look up nucleic acid in Wiktionary, the free dictionary. ... Lactose is a disaccharide found in milk. ... Nucleotide sugars are biochemicals that act as donors of sugar residues in nucleotide sugars metabolism. ... Some common lipids. ... Many terpenes are derived from conifer resins, here a pine. ... The orange ring surrounding Grand Prismatic Spring is due to carotenoid molecules, produced by huge mats of algae and bacteria. ... Polypyrrole A Polypyrrole (PPy) is a chemical compound formed from a number of connected pyrrole ring structures. ... A cofactor is any substance that needs to be present in addition to an enzyme to catalyze a certain reaction. ... This article is about the chemical family of steroids. ... Molecular structure of the flavone backbone (2-phenyl-1,4-benzopyrone) The term flavonoid refers to a class of plant secondary metabolites. ... Chemical structure of ephedrine, a phenethylamine alkaloid An alkaloid is, strictly speaking, a naturally occurring amine produced by a plant,[1] but amines produced by animals and fungi are also called alkaloids. ... Polyketides are secondary metabolites from bacteria, fungi, plants, and animals. ... A glycoside is a molecule where a sugar group is bonded through its anomeric carbon to a nonsugar group by either an oxygen or a nitrogen atom. ... Look up nucleic acid in Wiktionary, the free dictionary. ... Adenine Guanine Thymine Cytosine ... For the programming language Adenine, see Adenine (programming language). ... Guanine is one of the five main nucleobases found in the nucleic acids DNA and RNA; the others being adenine, cytosine, thymine, and uracil. ... Pyrimidine is a heterocyclic aromatic organic compound similar to benzene and pyridine, containing two nitrogen atoms at positions 1 and 3 of the six-member ring [1]. It is isomeric with two other forms of diazine. ... Uracil is a pyrimidine which is common and naturally occurring. ... For the similarly-spelled vitamin compound, see Thiamine Thymine, also known as 5-methyluracil, is a pyrimidine nucleobase. ... Cytosine is one of the 5 main nucleobases used in storing and transporting genetic information within a cell in the nucleic acids DNA and RNA. It is a pyrimidine derivative, with a heterocyclic aromatic ring and two substituents attached (an amine group at position 4 and a keto group at... Nucleosides are glycosylamines made by attaching a nucleobase (often reffered to simply as bases) to a ribose ring. ... Adenosine is a nucleoside composed of adenine attached to a ribose (ribofuranose) moiety via a Î²-N9-glycosidic bond. ... The chemical structure of adenosine Adenosine is a nucleoside formed when adenine is attached to a ribose ring (also known as a ribofuranose) via a β-N9-glycosidic bond. ... The chemical structure of Guanosine Guanosine is a nucleoside comprising guanine attached to a ribose (ribofuranose) ring via a Î²-N9-glycosidic bond. ... Guanosine is a molecule (known as a nucleoside) that is formed when guanine is attached to a ribose ring (also known as a ribofuranose) via a β-N9-glycosidic bond. ... Uridine is a molecule (known as a nucleoside) that is formed when uracil is attached to a ribose ring (also known as a ribofuranose) via a β-N1-glycosidic bond. ... The chemical structure of deoxythymidine Thymidine (more precisely called deoxythymidine can also be labelled deoxyribosylthymine, and thymine deoxyriboside) is a chemical compound, more precisely a pyrimidine deoxynucleoside. ... Cytidine is a molecule (known as a nucleoside) that is formed when cytosine is attached to a ribose ring (also known as a ribofuranose) via a β-N1-glycosidic bond. ... Cytidine is a molecule (known as a nucleoside) that is formed when cytosine is attached to a ribose ring (also known as a ribofuranose) via a β-N1-glycosidic bond. ... A nucleotide is a chemical compound that consists of 3 portions: a heterocyclic base, a sugar, and one or more phosphate groups. ... Adenosine monophosphate, also known as 5-adenylic acid and abbreviated AMP, is a nucleotide that is found in RNA. It is an ester of phosphoric acid with the nucleoside adenosine. ... Uridine monophosphate, also known as 5-uridylic acid and abbreviated UMP, is a nucleotide that is found in RNA. It is an ester of phosphoric acid with the nucleoside uridine. ... Guanosine monophosphate, also known as 5-guanidylic acid and abbreviated GMP, is a nucleotide that is found in RNA. It is an ester of phosphoric acid with the nucleoside guanosine. ... Cytidine monophosphate, also known as 5-cytidylic acid and abbreviated CMP, is a nucleotide that is found in RNA. It is an ester of phosphoric acid with the nucleoside cytidine. ... Adenosine diphosphate, abbreviated ADP, is a nucleotide. ... Uridine diphosphate, abbreviated UDP, is a nucleotide. ... Cytidine diphosphate, abbreviated CDP, is a nucleotide. ... Adenosine 5-triphosphate (ATP) is a multifunctional nucleotide that is most important as a molecular currency of intracellular energy transfer. ... Adenosine 5-triphosphate (ATP) is a multifunctional nucleotide primarily known in biochemistry as the molecular currency of intracellular energy transfer. ... Guanosine triphosphate (GTP) is also known as guanosine-5-triphosphate. ... Cytidine triphosphate is a pyrimidine nucleotide. ... Structure of cAMP cAMP represented in three ways, the left with sticks-representation, the middle with structure formula, and the right with space filled representation. ... Cyclic guanosine monophosphate (cGMP) is a second messenger derived from GTP. Cyclic guanosine monophosphate (cGMP) is a cyclic nucleotide derived from guanosine triphosphate (GTP). ... Cyclic ADP Ribose popularly known as cADPR is a cyclic adenine nucleotide (like cAMP) with two phosphate groups present on 5 OH of the adenosine (like ADP), further connected to another ribose at the 5 position which in turn closes the cycle by glycosidic bonding to the Nitrogen1 of the... A nucleotide is a monomer or the structural unit of nucleotide chains forming nucleic acids as RNA and DNA. A nucleotide consists of a heterocyclic nucleobase, a pentose sugar, and a phosphate or polyphosphate group. ... This article belongs in one or more categories. ... Thymidine monophosphate, also known as 5-thymidylic acid and abbreviated TMP, is a nucleotide that is found in RNA. It is an ester of phosphoric acid with the nucleoside thymidine. ... Deoxyguanosine monophosphate is a derivative of the common nucleic acid GTP, or guanosine triphosphate, in which the -OH (hydroxyl) group on the 2 carbon on the nucleotides pentose has been reduced to just a hydrogen atom (hence the deoxy- part of the name). ... Deoxycytidine monophosphate is a deoxynucleotide, and one of the four monomers that make up DNA. In a DNA double helix, it will base pair with deoxyguanosine monophosphate. ... Deoxyadenosine diphosphate is a derivative of the common nucleic acid ATP, or adenosine triphosphate, in which the -OH (hydroxyl) group on the 2 carbon on the nucleotides pentose has been removed (hence the deoxy- part of the name). ... Thymidine diphosphate, abbreviated TDP, is a nucleotide. ... Deoxyguanosine diphosphate is a derivative of the common nucleic acid GTP, or guanosine triphosphate, in which the -OH (hydroxyl) group on the 2 carbon on the nucleotides pentose has been removed (hence the deoxy- part of the name). ... Please wikify (format) this article or section as suggested in the Guide to layout and the Manual of Style. ... Deoxy adenosine triphosphate produces energy within the cells and is the basis for normal functioning of all body systems and organs. ... 3D-Model of thymidine triphosphate Thymidine triphosphate or TTP is one of the four nucleoside triphosphates that make up DNA. It can be used by DNA ligase to create overlapping sticky ends so that protruding ends of opened microbial plasmids maybe closed up. ... The chemical structure of dGTP Deoxyguanosine triphosphate, normally shortened to dGTP has a chemical structure of Na4 â€¢ 3 H2O and a molecular weight of 649. ... This article or section is in need of attention from an expert on the subject. ... For other uses, see RNA (disambiguation). ... For other uses, see RNA (disambiguation). ... The life cycle of an mRNA in a eukaryotic cell. ... Piwi-interacting RNA (piRNA) is a class of small RNA molecules that is expressed uniquely in mammalian testes and forms RNA-protein complexes with Piwi proteins. ... Transfer RNA Transfer RNA (abbreviated tRNA), first hypothesized by Francis Crick, is a small RNA chain (73-93 nucleotides) that transfers a specific amino acid to a growing polypeptide chain at the ribosomal site of protein synthesis during translation. ... Ribosomal RNA (rRNA), a type of RNA synthesized in the nucleolus by RNA Pol I, is the central component of the ribosome, the protein manufacturing machinery of all living cells. ... A non-coding RNA (ncRNA) is any RNA molecule that is not translated into a protein. ... Guide RNA (gRNA) is a type of RNA that is used in mRNA editing. ... A short hairpin RNA (shRNA) is a sequence of RNA that makes a tight hairpin turn that can be used in gene expression silence. ... Mediating RNA interference in cultured mammalian cells. ... A non-coding RNA (ncRNA) is any RNA molecule that functions without being translated into a protein. ... The stem-loop secondary structure of a pre-microRNA from Brassica oleracea. ... A non-coding RNA (ncRNA) is any RNA molecule that functions without being translated into a protein. ... The structure of part of a DNA double helix Deoxyribonucleic acid, or DNA, is a nucleic acid molecule that contains the genetic instructions used in the development and functioning of all known living organisms. ... The structure of part of a DNA double helix Deoxyribonucleic acid, or DNA, is a nucleic acid molecule that contains the genetic instructions used in the development and functioning of all known living organisms. ... Mitochondrial DNA (some captions in German) Mitochondrial DNA (mtDNA) is the DNA located in organelles called mitochondria. ... In genetics, complementary DNA (cDNA) is DNA synthesized from a mature mRNA template. ... Figure 1: Illustration of a bacterium with plasmids enclosed showing chromosomal DNA and plasmids. ... A cosmid is a type of plasmid (often used as a cloning vector) constructed by the insertion of cos sequences, DNA-Sequences of the Phage Lambda Virus. ... A bacterial artificial chromosome (BAC) is a DNA construct, based on a fertility plasmid (or F-plasmid), used for transforming and cloning in bacteria, usually E. coli. ... A yeast artificial chromosome (short YAC) is a vector used to clone large DNA fragments (larger than 100 kb and up to 3000 kb). ... A human artificial chromosome (short HAC) is a microchromosome that can act as a new chromosome in a population of human cells. ... Look up nucleic acid in Wiktionary, the free dictionary. ... Glycerol nucleic acid (GNA) is a chemical similar to DNA or RNA but differing in the composition of its backbone. GNA is not known to occur naturally in existing life on Earth. ... PNA can also refer to the Palestinian National Authority or Pakistan National Alliance. ... TNA is threose nucleic acid, a chemical similar to DNA or RNA but differing in the composition of its backbone. ... Segment of a Morpholino-RNA heteroduplex, 8-mer shown In molecular biology, a Morpholino is a kind of molecule used to modify gene expression. ... A locked nucleic acid (LNA) is a modified RNA nucleotide. ...

Contents

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