NationMaster - Encyclopedia: Guanine

Guanine is one of the five main nucleobases found in the nucleic acids DNA and RNA; the others being adenine, cytosine, thymine, and uracil. With the formula C₅H₅N₅O, guanine is a derivative of purine, consisting of a fused pyrimidine-imidazole ring system with conjugated double bonds. Being unsaturated, the bicyclic molecule is planar. The guanine nucleoside is called guanosine. The flash point of a flammable liquid is the lowest temperature at which it can form an ignitable mixture with air. ... Risk and Safety Statements, also known as R/S statements, R/S numbers, R/S phrases, and R/S sentences, is a system of hazard codes and phrases for labeling dangerous chemicals and compounds. ... R-phrases are defined in Annex III of European Union Directive 67/548/EEC: Nature of special risks attributed to dangerous substances and preparations. ... S-phrases are defined in Annex IV of European Union Directive 67/548/EEC: Safety advice concerning dangerous substances and preparations. ... RTECS, also known as Registry of Toxic Effects of Chemical Substances, is a database of toxicity information compiled from the open scientific literature that is available for charge. ... The refractive index (or index of refraction) of a medium is a measure for how much the speed of light (or other waves such as sound waves) is reduced inside the medium. ... The relative dielectric constant of a material under given conditions is a measure of the extent to which it concentrates electrostatic lines of flux. ... Ultraviolet-Visible Spectroscopy or Ultraviolet-Visible Spectrophotometry (UV/ VIS) involves the spectroscopy of photons (spectrophotometry). ... Infrared spectroscopy (IR Spectroscopy) is the subset of spectroscopy that deals with the IR region of the EM spectrum. ... Nuclear Magnetic Resonance Spectroscopy most commonly known as NMR Spectroscopy is the name given to the technique which exploits the magnetic properties of nuclei. ... Mass spectrometry (also known as mass spectroscopy (deprecated)[1] or in common speech mass-spec) is an analytical technique used to measure the mass-to-charge ratio of ions. ... â€œMultivalentâ€ redirects here. ... â€œMultivalentâ€ redirects here. ... 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... This article or section does not adequately cite its references or sources. ... For the similarly-spelled vitamin compound, see Thiamine Thymine, also known as 5-methyluracil, is a pyrimidine nucleobase. ... Uracil is a pyrimidine which is common and naturally occurring. ... In chemistry, the standard state of a material is its state at 1 bar (100 kilopascals) and 25 degrees Celsius (298. ... Adenine Guanine Thymine Cytosine ... A nucleic acid is a complex, high-molecular-weight biochemical macromolecule composed of nucleotide chains that convey genetic information. ... The structure of part of a DNA double helix Deoxyribonucleic acid (DNA) is a nucleic acid that contains the genetic instructions for the development and function of living organisms. ... This article or section does not adequately cite its references or sources. ... This article or section does not adequately cite its references or sources. ... 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 the similarly-spelled vitamin compound, see Thiamine Thymine, also known as 5-methyluracil, is a pyrimidine nucleobase. ... Uracil is a pyrimidine which is common and naturally occurring. ... Purine is a heterocyclic aromatic organic compound, consisting of a pyrimidine ring fused to an imidazole ring. ... Nucleosides are glycosylamines made by attaching a nucleobase (often reffered to simply as bases) to a ribose ring. ... The chemical structure of Guanosine Guanosine is a nucleoside comprising guanine attached to a ribose (ribofuranose) ring via a Î²-N9-glycosidic bond. ...

Basic principles

Guanine, along with adenine and cytosine, is present in both DNA and RNA, whereas thymine is usually seen only in DNA and uracil only in RNA. Guanine has two tautomeric forms, the keto form and enol form. It binds to cytosine through three hydrogen bonds. In cytosine, the amino group acts as the hydrogen donor and the C-2 carbonyl and the N-3 amine as the hydrogen-bond acceptors. Guanine has a group at C-6 that acts as the hydrogen acceptor, while the group at N-1 and the amino group at C-2 acts as the hydrogen donors. In organic chemistry, keto-enol tautomerism refers to a chemical equilibrium between a keto form (a ketone or an aldehyde) 1 and an enol 2. ... Snapshot from a simulation of liquid water. ...

Image File history File links Cytonum2. ... Image File history File links Guannum2. ...

Isolation, background, & some chemistry

The first isolation of guanine was reported in 1844 from the excreta of sea birds, known as guano, which was used as a source of fertilizer. About fifty years later, Fischer determined the structure and also showed that uric acid can be converted to guanine. The first complete synthesis was done by Traube and remains among the best large-scale preparations.

Guanine can be hydrolyzed with strong acid to glycine, ammonia, carbon dioxide, and carbon monoxide at 180°C. Guanine oxidizes more readily than adenine, the other purine-derivative base in DNA and RNA. Its high melting point of 350°C reflects the intermolecular hydrogen bonding between the oxo and amino groups in the molecules in the crystal. Because of this intermolecular bonding, guanine is relatively insoluble in water, although it is soluble in dilute acids and bases.

Syntheses

Trace amounts of guanine form by the polymerization of ammonium cyanide (NH₄CN). Two experiments conducted by Levy et al., showed that heating 10 M NH₄CN at 80°C for 24 hours gave a yield of 0.0007% while using 0.1 M NH₄CN frozen at -20°C for 25 years gave a 0.0035% yield. These results indicate guanine could arise in frozen regions of the primitive earth. In 1984, Yuasa reported a 0.00017% yield of guanine after the electrical discharge of NH₃, CH₄, C₂H₆, and 50 mL of water, followed by a subsequent acid hydrolysis. However, it is unknown if the presence of guanine was not simply resulted from a contaminant of the reaction^{[citation needed]}.

A Fischer-Tropsch synthesis can also be used to form guanine, along with adenine, uracil and thymine. Heating an equimolar gas mixture of CO, H₂, and NH₃ to 700 °C for 0.24 to 0.4 hours, followed by quick cooling and then sustainted reheating to 100-200°C for 16-44 hours with an alumina catalyst yielded guanine and uracil:

Traube's synthesis involves heating 2,4,5-triamino-1,6-dihydro-6-oxypyrimidine (as the sulphate) with formic acid for several hours.

Image File history File links Download high-resolution version (1411x358, 11 KB) I, the creator of this work, hereby release it into the public domain. ...

Other uses

In 1656 in Paris, François Jaquin (a rosary maker) extracted from scales of some fishes the so called pearl essence, crystalline guanine forming G-quadruplexes: in cosmetic industry, crystalline guanine is used as an additive to various products (e.g., shampoos), where it provides the pearly iridescent effect. It is also used in metallic paints and simulated pearls and plastics. It provides shimmering lustre to eye shadow and nail polish. Guanine crystals are rhombic platelets composed of multiple, transparent layers but they have a high index of refraction that partially reflects and transmits light from layer to layer thus producing a pearly luster. It can be applied by spray, painting or dipping. It may irritate eyes. Its alternatives are mica, synthetic pearl, and aluminium and bronze particles. Nucleic acid sequences which are rich in guanine are capable of forming four-stranded structures called G-quadruplexes (Also known as G-tetrads or G4-DNA). ... This article does not cite its references or sources. ... The iridescence of the Blue Morpho butterfly wings. ... Pink nail polish. ... Rock with mica Mica sheet Mica flakes The mica group of sheet silicate minerals includes several closely related materials having highly perfect basal cleavage. ... Strand of akoya pearls from China Pearl farm, Seram, Indonesia A pearl is a hard, rounded object produced by certain animals, primarily mollusks such as oysters. ... General Name, Symbol, Number aluminium, Al, 13 Chemical series poor metals Group, Period, Block 13, 3, p Appearance silvery Standard atomic weight 26. ... Assorted ancient Bronze castings found as part of a cache, probably intended for recycling. ...

References

1. Miyakawa, S., Murasawa, K., Kobayashi, K., Sawaoka, AB. "Abiotic synthesis of guanine with high-temperature plasma." Orig Life Evol Biosph. 30(6): 557-66, Dec. 2000.
2. Horton, H.R., Moran, L.A., Ochs, R.S., Rawn, J.D., Scrimgeour, K.G. "Principles of Biochemistry." Prentice Hall (New Jersey). 3rd Edition, 2002.
3. Lister, J.H. "Part II Purines." The Chemistry of Heterocyclic Compounds. Wiley-Interscience (New York). 1971.

External links

Categories: Articles with unsourced statements since February 2007 | All articles with unsourced statements | Purines | Cosmetic chemicals | Organic minerals Biochemistry is the study of the chemical processes and transformations 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. ... Phenylalanine is one of the standard amino acids. ... A nucleic acid is a complex, high-molecular-weight biochemical macromolecule composed of nucleotide chains that convey genetic information. ... Lactose is a disaccharide found in milk. ... A polyunsaturated triglyceride. ... 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. ... Steroid skeleton of lanosterol. ... Molecular structure of flavone The term flavonoid refers to a class of plant secondary metabolites based around a phenylbenzopyrone structure. ... Diagram of Ephedrine An alkaloid, strictly speaking, is 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. ... A nucleic acid is a complex, high-molecular-weight biochemical macromolecule composed of nucleotide chains that convey genetic information. ... Adenine Guanine Thymine Cytosine ... This article or section does not adequately cite its references or sources. ... For the similarly-spelled vitamin compound, see Thiamine Thymine, also known as 5-methyluracil, is a pyrimidine nucleobase. ... Uracil is a pyrimidine which is common and naturally occurring. ... 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... Purine is a heterocyclic aromatic organic compound, consisting of a pyrimidine ring fused to an imidazole ring. ... 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. ... Nucleosides are glycosylamines made by attaching a nucleobase (often reffered to simply as bases) to a ribose ring. ... Adenosine is a nucleoside comprised of adenine attached to a ribose (ribofuranose) moiety via a Î²-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 Guanosine Guanosine is a nucleoside comprising guanine attached to a ribose (ribofuranose) ring via a Î²-N9-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. ... 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 deoxythymidine Thymidine (more precisely called deoxythymidine can also be labelled deoxyribosylthymine, and thymine deoxyriboside) is a chemical compound, more precisely a pyrimidine deoxynucleoside. ... 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. ... 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 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. ... Adenosine 5-triphosphate (ATP) is a multifunctional nucleotide primarily known in biochemistry as the molecular currency of intracellular energy transfer. ... 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 gruops 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 removed (hence the deoxy- part of the name). ... 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. ... This article or section does not adequately cite its references or sources. ... This article or section does not adequately cite its references or sources. ... 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. ... It has been suggested that Queuine be merged into this article or section. ... A non-coding RNA (ncRNA) is any RNA molecule that functions without being translated into a protein. ... A non-coding RNA (ncRNA) is any RNA molecule that is not translated into a protein. ... A short hairpin RNA (shRNA) is a sequence of RNA that makes a tight hairpin turn that can be used in gene expression silence. ... Small interfering RNA (siRNA), sometimes known as short interfering RNA, are a class of 20-25 nucleotide-long RNA molecules that interfere with the expression of genes. ... A non-coding RNA (ncRNA) is any RNA molecule that functions without being translated into a protein. ... The title given to this article is incorrect due to technical limitations. ... A non-coding RNA (ncRNA) is any RNA molecule that functions without being translated into a protein. ... A locked nucleic acid (LNA) is a modified RNA nucleotide. ... The structure of part of a DNA double helix Deoxyribonucleic acid (DNA) is a nucleic acid that contains the genetic instructions for the development and function of living organisms. ... The structure of part of a DNA double helix Deoxyribonucleic acid (DNA) is a nucleic acid that contains the genetic instructions for the development and function of living organisms. ... // Mitochondrial DNA (mtDNA) is DNA that is located in mitochondria. ... In genetics, complementary DNA (cDNA) is DNA synthesized from a mature mRNA template. ... Figure 1: Schematic drawing of a bacterium with plasmids enclosed. ... 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. ... A nucleic acid is a complex, high-molecular-weight biochemical macromolecule composed of nucleotide chains that convey genetic information. ... GNA is glycol nucleic acid, a chemical similar to DNA or RNA but differing in the composition of its backbone. ... PNA is peptide nucleic acid, a chemical similar to DNA or RNA but differing in the composition of its backbone. ... TNA is threose nucleic acid, a chemical similar to DNA or RNA but differing in the composition of its backbone. ... Morpholino oligos are an antisense technology used to block access of other molecules to specific sequences within nucleic acid molecules. ...

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