Array ( [0] => {{Short description|Chemical compound of DNA and RNA}} [1] => {{Distinguish|Guanosine|Guanidine|Guanfacine|Guanamine|Guanín}} [2] => {{chembox [3] => | Watchedfields = changed [4] => | verifiedrevid = 443850318 [5] => | ImageFile1 = Guanin.svg [6] => | ImageSize1 = 150px [7] => | ImageFileL2 = Guanine-3D-balls.png [8] => | ImageFileR2 = Guanine-3D-vdW.png [9] => | PIN = 2-Amino-1,9-dihydro-6''H''-purin-6-one [10] => | OtherNames = 2-amino-6-hydroxypurine,
2-aminohypoxanthine,
Guanine [11] => |Section1={{Chembox Identifiers [12] => | IUPHAR_ligand = 4556 [13] => | DrugBank_Ref = {{drugbankcite|correct|drugbank}} [14] => | DrugBank = DB02377 [15] => | ChEBI_Ref = {{ebicite|correct|EBI}} [16] => | ChEBI = 16235 [17] => | SMILES = O=C1c2ncnc2nc(N)N1 [18] => | SMILES_Comment = keto form [19] => | SMILES1 = Oc1c2ncnc2nc(N)n1 [20] => | SMILES1_Comment = enol form [21] => | UNII_Ref = {{fdacite|correct|FDA}} [22] => | UNII = 5Z93L87A1R [23] => | KEGG_Ref = {{keggcite|correct|kegg}} [24] => | KEGG = C00242 [25] => | InChI = 1/C5H5N5O/c6-5-9-3-2(4(11)10-5)7-1-8-3/h1H,(H4,6,7,8,9,10,11) [26] => | InChIKey = UYTPUPDQBNUYGX-UHFFFAOYAE [27] => | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} [28] => | ChemSpiderID = 744 [29] => | ChEMBL_Ref = {{ebicite|correct|EBI}} [30] => | ChEMBL = 219568 [31] => | PubChem = 135398634 [32] => | EC_number = 200-799-8 [33] => | Beilstein = 147911 [34] => | Gmelin = 431879 [35] => | StdInChI_Ref = {{stdinchicite|correct|chemspider}} [36] => | StdInChI = 1S/C5H5N5O/c6-5-9-3-2(4(11)10-5)7-1-8-3/h1H,(H4,6,7,8,9,10,11) [37] => | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} [38] => | StdInChIKey = UYTPUPDQBNUYGX-UHFFFAOYSA-N [39] => | CASNo = 73-40-5 [40] => | CASNo_Ref = {{cascite|correct|CAS}} [41] => | RTECS = MF8260000 [42] => }} [43] => |Section2={{Chembox Properties [44] => | Formula = C5H5N5O [45] => | MolarMass = 151.13 g/mol [46] => | Appearance = White amorphous solid. [47] => | Density = 2.200 g/cm3 (calculated) [48] => | Solubility = Insoluble. [49] => | MeltingPtC = 360 [50] => | MeltingPt_notes = decomposes [51] => | BoilingPt = Sublimes [52] => | pKa =3.3 (amide), 9.2 (secondary), 12.3 (primary)Dawson, R.M.C., et al., ''Data for Biochemical Research'', Oxford, Clarendon Press, 1959. [53] => | Dipole = [54] => }} [55] => |Section7={{Chembox Hazards [56] => | MainHazards = Irritant [57] => | NFPA-H = 1 [58] => | NFPA-F = 1 [59] => | NFPA-R = [60] => | FlashPt = Non-flammable [61] => }} [62] => |Section8={{Chembox Related [63] => | OtherAnions = [64] => | OtherCations = [65] => | OtherCompounds = [[Cytosine]]; [[Adenine]]; [[Thymine]]; [[Uracil]] [66] => }} [67] => }} [68] => '''Guanine''' ({{IPAc-en|audio=En-us-guanine.ogg|ˈ|g|w|ɑː|n|ᵻ|n}}) ([[nucleoside#List of nucleosides and corresponding nucleobases|symbol]] '''G''' or '''Gua''') is one of the four main [[nucleobase]]s found in the [[nucleic acid]]s [[DNA]] and [[RNA]], the others being [[adenine]], [[cytosine]], and [[thymine]] ([[uracil]] in RNA). In [[DNA]], guanine is paired with cytosine. The guanine [[nucleoside]] is called [[guanosine]]. [69] => [70] => With the formula C5H5N5O, guanine is a derivative of [[purine]], consisting of a fused [[pyrimidine]]-[[imidazole]] ring system with conjugated double bonds. This unsaturated arrangement means the [[bicyclic molecule]] is planar. [71] => [72] => ==Properties== [73] => 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 [[tautomer]]ic forms, [[keto-enol tautomerism|the major keto form (see figures) and rare enol form]].{{cn|date=February 2024}} [74] => [75] => It binds to cytosine through three [[hydrogen bond]]s. In cytosine, the amino group acts as the hydrogen bond donor and the C-2 carbonyl and the N-3 amine as the hydrogen-bond acceptors. Guanine has the C-6 carbonyl group that acts as the hydrogen bond acceptor, while a group at N-1 and the amino group at C-2 act as the hydrogen bond donors.{{cn|date=February 2024}} [76] => [77] => {{multiple image [78] => | align=center [79] => | total_width = 400 [80] => | image1=Cytonum2.svg [81] => | caption1=[[Cytosine]] [82] => | image2=Guannum2.svg [83] => | caption2=Guanine [84] => | footer=Cytosine and guanine with the direction of hydrogen bonding indicated (arrow points positive to negative charge) [85] => }} [86] => [87] => Guanine can be [[hydrolyzed]] with strong acid to [[glycine]], [[ammonia]], [[carbon dioxide]], and [[carbon monoxide]]. First, guanine gets [[Deamination|deaminated]] to become [[xanthine]].{{cite journal |last=Angstadt | title=Purines and pyrimidines | url=http://library.med.utah.edu/NetBiochem/pupyr/pp.htm |access-date=2008-03-27}} Guanine oxidizes more readily than adenine, the other purine-derivative base in DNA. 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, but it is soluble in dilute acids and bases. [88] => [89] => ==History== [90] => The first isolation of guanine was reported in 1844 by the German chemist {{ill|Julius Bodo Unger|de|Bodo Unger (Chemiker)}} (1819–1885), who obtained it as a mineral formed from the excreta of sea birds, which is known as [[guano]] and which was used as a source of fertilizer; guanine was named in 1846.Guanine was first isolated in 1844 by Julius Bodo Unger (1819–1885), a student of [[Heinrich Gustav Magnus]]. See: [91] => * [[Paul O. P. Ts'o]], ''Basic Principles in Nucleic Acid Chemistry'', vol. 1 (New York, New York: Academic Press, 1974), [https://books.google.com/books?id=oAKAbV7FHfgC&pg=PA7 page 7.] [92] => * Magnus (1844) [https://books.google.com/books?id=nT49AAAAcAAJ&pg=PA395 "Ueber das Vorkommen von Xanthicoxyd im Guano"] (On the occurrence of xanthic oxide in guano), ''Annalen der Chemie und Pharmacie'', '''51''' : 395-397. [93] => * B. Unger (1846) [https://books.google.com/books?id=7TU9AAAAcAAJ&pg=PA18 "Bemerkungen zu obiger Notiz"] (Comments on the above notice), ''Annalen der Chemie und Pharmacie'', '''58''' : 18-20. From page 20: ''" ... desshalb möchte ich den Namen ''Guanin'' vorschlagen, welcher an seine Herkunft erinnert."'' ( ... therefore I would like to suggest the name ''guanine'', which is reminiscent of its origin.) [94] => * B. Unger (1846) [https://books.google.com/books?id=AjY9AAAAcAAJ&pg=PA58 "Das Guanin und seine Verbindungen"] (Guanine and its compounds), ''Annalen der Chemie und Pharmacie'', '''59''' : 58-68. Between 1882 and 1906, [[Hermann Emil Fischer|Emil Fischer]] determined the structure and also showed that [[uric acid]] can be converted to guanine.{{cite web |title = Emil Fischer - Biographical |url=https://www.nobelprize.org/nobel_prizes/chemistry/laureates/1902/fischer-bio.html}} [95] => [96] => ==Synthesis== [97] => Trace amounts of guanine form by the [[polymerization]] of [[ammonium cyanide]] ({{chem|NH|4|CN}}). Two experiments conducted by Levy et al. showed that heating 10 mol·L−1 {{chem|NH|4|CN}} at 80 °C for 24 hours gave a yield of 0.0007%, while using 0.1 mol·L−1 {{chem|NH|4|CN}} 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 {{chem|NH|3}}, {{chem|CH|4}}, {{chem|C|2|H|6}}, and 50 mL of water, followed by a subsequent acid hydrolysis. However, it is unknown whether the presence of guanine was not simply a resultant contaminant of the reaction.{{cite journal | last = Levy | first = Matthew |author2=Stanley L. Miller |author3=John Oró | title = Production of Guanine from NH4CN Polymerizations | journal = Journal of Molecular Evolution | volume = 49 | issue = 2 | pages = 165–8 |date=August 1999 | doi = 10.1007/PL00006539 | pmid = 10441668| bibcode = 1999JMolE..49..165L | s2cid = 32194418 }} - quotes the Yuasa paper and cites the possibility of there being a contaminant in the reaction. [98] => [99] => :10NH3 + 2CH4 + 4C2H6 + 2H2O → 2C5H8N5O (guanine) + 25H2 [100] => [101] => 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 15 to 24 minutes, followed by quick cooling and then sustained reheating to 100 to 200 °C for 16 to 44 hours with an alumina catalyst, yielded guanine and uracil: [102] => :10CO + H2 + 10NH3 → 2C5H8N5O (guanine) + 8H2O [103] => [104] => Another possible abiotic route was explored by quenching a 90% N2–10%CO–H2O gas mixture high-temperature plasma.{{cite journal | last = Miyakawa | first = S |author2=Murasawa, K. |author3=Kobayashi, K. |author4=Sawaoka, AB. | title = Abiotic synthesis of guanine with high-temperature plasma | journal = Orig Life Evol Biosph | volume = 30 | issue = 6 | pages = 557–66 |date=December 2000 | doi = 10.1023/A:1026587607264 | pmid = 11196576| bibcode = 2000OLEB...30..557M | s2cid = 25417484 }} [105] => [106] => [[Traube purine synthesis|Traube's synthesis]] involves heating 2,4,5-triamino-1,6-dihydro-6-oxypyrimidine (as the sulfate) with [[formic acid]] for several hours. [107] => [[Image:TraubePurineSynthesis.svg|Traube purine synthesis]] [108] => [109] => ==Biosynthesis== [110] => Guanine is not synthesized [[de novo synthesis|de novo]]{{clarification needed|date=March 2022}}, instead it's split from the more complex molecule, [[guanosine]], by the enzyme [[guanosine phosphorylase]]: [111] => [112] => :guanosine + phosphate \rightleftharpoons guanine + alpha-D-ribose 1-phosphate [113] => Guanine can be synthesized de novo, with the rate-limiting enzyme of [[Inosine-5′-monophosphate dehydrogenase|inosine monophosphate dehydrogenase]]. [114] => [115] => ==Other occurrences and biological uses== [116] => The word guanine derives from the Spanish loanword ''guano'' ("bird/bat droppings"), which itself is from the [[Quechua language|Quechua]] word ''wanu'', meaning "dung". As the [[Oxford English Dictionary]] notes, guanine is "A white amorphous substance obtained abundantly from guano, forming a constituent of the excrement of birds".OED. "guanine" and also "guano". [117] => [118] => In 1656 in Paris, a Mr. Jaquin extracted from the scales of the fish [[Common bleak|''Alburnus alburnus'']] so-called "pearl essence",Johann Rudolf von Wagner, Ferdinand Fischer, and L. Gautier, ''Traité de chimie industrielle'' (Treatise on industrial chemistry), 4th ed., (Paris, France: Masson & Co., 1903), vol. 2, [https://books.google.com/books?id=K2mhGDwiSJsC&pg=PA64 pp. 64–65.] which is crystalline guanine.In 1861 the French chemist [[Charles-Louis Barreswil]] (1817–1870) found that "pearl essence" was guanine. See: Barreswil (1861) [http://gallica.bnf.fr/ark:/12148/bpt6k3010v/f246.item.zoom "Sur le blanc d'ablette qui sert à la fabrication des perles fausses"] (On the white of ablette that's used in making imitation pearls), ''Comptes rendus'', '''53''' : 246. In the cosmetics industry, crystalline guanine is used as an additive to various products (e.g., shampoos), where it provides a pearly [[iridescence|iridescent]] effect. It is also used in metallic paints and simulated pearls and plastics. It provides shimmering luster to eye shadow and [[nail polish]]. Facial treatments using the droppings, or guano, from Japanese nightingales have been used in Japan and elsewhere, because the guanine in the [[Uguisu no fun|dropping]]s makes the skin look paler.{{cite web |title=Geisha facial, the 'latest beauty secret' of Victoria Beckham, brought to the masses |last=Whitworth |first=Melissa |date=2008-10-16 |access-date=2008-11-20 |url=https://www.telegraph.co.uk/fashion/beauty/3365670/Geisha-facial%2C-the-%27latest-beauty-secret%27-of-Victoria-Beckham%2C-brought-to-the-masses.html |archive-url=https://web.archive.org/web/20081205010654/http://www.telegraph.co.uk/fashion/beauty/3365670/Geisha-facial%2C-the-%27latest-beauty-secret%27-of-Victoria-Beckham%2C-brought-to-the-masses.html |url-status=dead |archive-date=2008-12-05 |publisher=Telegraph |work=Lifestyle}} 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 the eyes. Its alternatives are [[mica]], faux pearl (from ground shells),{{cite journal | title= How Pearls are Made...Faux, Fake, Imitation, Simulated or Man-made | url = http://www.karipearls.com/how-pearls-are-made.html}} and [[aluminium]] and [[bronze]] particles. [119] => [120] => Guanine has a very wide variety of biological uses that include a range of functions ranging in both complexity and versatility. These include camouflage, display, and vision among other purposes. [121] => [122] => Spiders, scorpions, and some amphibians convert ammonia, as a product of protein metabolism in the cells, to guanine, as it can be excreted with minimal water loss.{{Cite journal |date=2017|title=Light manipulation by guanine crystals in organisms: biogenic scatterers, mirrors, multilayer reflectors and photonic crystals.|journal=Advanced Functional Materials|volume=27 | issue = 6 |page=1603514|doi=10.1002/adfm.201603514|last1=Gur|first1=Dvir|last2=Palmer|first2=Benjamin A.|last3=Weiner|first3=Steve|last4=Addadi|first4=Lia|s2cid=136383728 }} [123] => [124] => Guanine is also found in specialized skin cells of fish called [[iridocyte]]s (e.g., the [[sturgeon]]), as well as being present in the reflective deposits of the eyes of [[deep-sea fish]] and some [[reptile]]s, such as [[crocodile]]s and [[chameleon]]s.{{cite book |last=Fox |first=D.L. |year=1979 |title=Biochromy, natural coloration of living things |publisher=University of California Press |isbn=978-0-520-03699-4}} [125] => [126] => On 8 August 2011, a report, based on [[NASA]] studies with [[meteorites]] found on Earth, was published suggesting building blocks of DNA and RNA (guanine, [[adenine]] and related [[organic molecules]]) may have been formed extra-terrestrially in outer space.{{cite journal |last1=Callahan |last2=Smith |first2=K.E. |last3=Cleaves |first3=H.J. |last4=Ruzica |first4=J. |last5=Stern |first5=J.C. |last6=Glavin |first6=D.P. |last7=House |first7=C.H. |last8=Dworkin |first8=J.P. |date=11 August 2011 |title=Carbonaceous meteorites contain a wide range of extraterrestrial nucleobases |publisher=[[PNAS]] |doi=10.1073/pnas.1106493108 |pmid=21836052 |pmc=3161613 |volume=108 |issue=34 |journal=Proc. Natl. Acad. Sci. U.S.A. |pages=13995–8|bibcode=2011PNAS..10813995C |doi-access=free }}{{cite web |last=Steigerwald |first=John |title=NASA Researchers: DNA Building Blocks Can Be Made in Space|url=http://www.nasa.gov/topics/solarsystem/features/dna-meteorites.html|publisher=[[NASA]]|date=8 August 2011 |access-date=2011-08-10}}{{cite web |author=ScienceDaily Staff |title=DNA Building Blocks Can Be Made in Space, NASA Evidence Suggests|url=https://www.sciencedaily.com/releases/2011/08/110808220659.htm|date=9 August 2011 |website=[[ScienceDaily]]|access-date=2011-08-09}} [127] => [128] => ==See also== [129] => * [[Cytosine]] [130] => * [[Guanine deaminase]] [131] => [132] => ==References== [133] => {{Reflist}} [134] => [135] => ==External links== [136] => {{Commons category|Guanine}} [137] => * [http://gmd.mpimp-golm.mpg.de/Spectrums/d84fcceb-5982-470a-a0d5-03450fb8aa47.aspx Guanine MS Spectrum] [138] => * [http://www.chemicalland21.com/lifescience/phar/GUANINE.htm Guanine] at chemicalland21.com [139] => [140] => {{Nucleobases, nucleosides, and nucleotides}} [141] => {{Purinergics}} [142] => {{Authority control}} [143] => [144] => [[Category:Nucleobases]] [145] => [[Category:Purines]] [146] => [[Category:Cosmetics chemicals]] [147] => [[Category:Organic minerals]] [] => )
good wiki

Guanine

Guanine (symbol G or Gua) is one of the four main nucleobases found in the nucleic acids DNA and RNA, the others being adenine, cytosine, and thymine (uracil in RNA). In DNA, guanine is paired with cytosine.

More about us

About

Expert Team

Vivamus eget neque lacus. Pellentesque egauris ex.

Award winning agency

Lorem ipsum, dolor sit amet consectetur elitorceat .

10 Year Exp.

Pellen tesque eget, mauris lorem iupsum neque lacus.

You might be interested in

Adenine

Adenine is a nucleobase, which is a component of nucleotides, the basic building blocks of DNA and RNA.

Aluminium

Aluminium is a chemical element with the symbol Al and atomic number 13.

Ammonia

Ammonia is a compound composed of one nitrogen atom bonded to three hydrogen atoms.

Cytosine

Cytosine (symbol C or Cyt) is one of the four nucleobases found in DNA and RNA, along with adenine, guanine, and thymine (uracil in RNA).

DNA

DNA, also known as deoxyribonucleic acid, is a molecule that carries the genetic instructions used in the growth, development, functioning, and reproduction of all known living organisms and many viruses.

NASA

NASA (National Aeronautics and Space Administration) is an independent agency of the United States federal government responsible for the country's civilian space program and for aeronautics and aerospace research.

Polymerization

In polymer chemistry, polymerization (American English), or polymerisation (British English), is a process of reacting monomer molecules together in a chemical reaction to form polymer chains or three-dimensional networks.

RNA

RNA (Ribonucleic acid) is a molecule that is essential for life and plays a crucial role in protein synthesis, gene regulation, and other cellular processes.