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Guanine

Guanine (/ˈɡwɑːnɪn/; or G, Gua) is one of the four main nucleobases found in the
Guanine
nucleic acids 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.

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.

Contents
Properties
Names
History
Syntheses IUPAC name
Other occurrences/ biological uses
2-amino-9H-purin-6(1H)-one

See also Other names


References 1,9-dihydro-6H-purin-6-one,
2-amino-6-hydroxypurine,
External links
2-aminohypoxanthine,
Guanine

Properties Identifiers
CAS Number 73-40-5
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 3D model Interactive image
two tautomeric forms, the major keto form (see figures) and rare enol form
. (JSmol)
ChEBI CHEBI:16235
It binds to cytosine through three hydrogen bonds. In cytosine, the amino group acts
as the hydrogen bond donor and the C-2 carbonyl and the N-3 amine as the ChEMBL ChEMBL219568
hydrogen-bond acceptors. Guanine has the C-6 carbonyl group that acts as the ChemSpider 744
hydrogen bond acceptor, while a group at N-1 and the amino group at C-2 act as the
DrugBank DB02377
hydrogen bond donors.
ECHA 100.000.727
InfoCard
IUPHAR/BPS 4556

KEGG C00242
RTECS MF8260000
number
UNII 5Z93L87A1R

InChI
SMILES
Properties
Chemical C5H5N5O
formula
formula
Molar mass 151.13 g/mol
Appearance White amorphous
solid.
Density 2.200 g/cm3
(calculated)
Melting point 360 °C (680 °F;
633 K) decomposes
Boiling point Sublimes
Solubility in Insoluble.
water
Acidity (pKa) 3.3 (amide), 9.2
(secondary), 12.3
(primary)[1]
Hazards
Main hazards Irritant
NFPA 704
1
1

Flash point Non-flammable


Related compounds
Related Cytosine; Adenine;
compounds Thymine; Uracil
Except where otherwise noted, data
are given for materials in their
standard state (at 25 °C [77 °F],
100 kPa).
verify (what is ?)
Infobox references

Guanine can be hydrolyzed with strong acid to glycine, ammonia, carbon dioxide, and carbon monoxide. First, guanine gets
deaminated to become xanthine.[2] 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.

History
The first isolation of guanine was reported in 1844 by the German chemist Julius Bodo Unger (1819–1885), who obtained it 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.[3] Between
1882 and 1906, Fischer determined the structure and also showed thaturic acid can be converted to guanine.[4]

Syntheses
Trace amounts of guanine form by the polymerization of ammonium cyanide (NH4CN). Two experiments conducted by Levy et al.
showed that heating 10 mol·L−1 NH4CN at 80 °C for 24 hours gave a yield of 0.0007%, while using 0.1 mol·L−1 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 whether the presence of guanine was not simply a resultant contaminant of the
reaction.[5]

10NH3 + 2CH4 + 4C2H6 + 2H2O → 2C5H8N5O (guanine) + 25H2

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:

10CO + H2 + 10NH3 → 2C5H8N5O (guanine) + 8H2O

Another possible abiotic route was explored by quenching a 90% N [6]


2–10%CO–H2O gas mixture high-temperature plasma.

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

Other occurrences/ biological uses


The word guanine derives from the Spanish loanword guano ("bird/bat droppings"), which itself is from the Quechua word wanu,
meaning "dung". As the Oxford English Dictionary notes, guanine is "A white amorphous substance obtained abundantly from
[7]
guano, forming a constituent of the excrement of birds".

In 1656 in Paris, a Mr. Jaquin extracted from the scales of the fish Alburnus alburnus so-called "pearl essence",[8] which is crystalline
guanine.[9] In the cosmetics industry, crystalline guanine is used as an additive to various products (e.g., shampoos), where it provides
a pearly 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, reportedly because the guanine in the droppings produces a clear, "bright" skin tone[10] that users desire. 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 aremica, faux pearl (from ground shells),[11] and aluminium and bronze particles.

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.[12]
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.[12]

Guanine is also found in specialized skin cells of fish called iridocytes (e.g., the sturgeon),[13][12] as well as being present in the
reflective deposits of the eyes ofdeep-sea fish and some reptiles, such as crocodiles.[13]

On 8 August 2011, a report, based on NASA studies with meteorites found on Earth, was published suggesting building blocks of
[14][15][16]
DNA and RNA (guanine,adenine and related organic molecules) may have been formed extra-terrestrially in outer space.

See also
Cytosine
Guanine deaminase

References
1. Dawson, R.M.C., et al.,Data for Biochemical Research, Oxford, Clarendon Press, 1959.
2. Angstadt. "Purines and pyrimidines"(http://library.med.utah.edu/NetBiochem/pupyr/pp.htm). Retrieved 2008-03-27.
3. Guanine was first isolated in 1844 by Julius Bodo Unger (1819–1885), a student of Prof.
Heinrich Gustav Magnus.
See:

Paul O. P. Ts'o, Basic Principles in Nucleic Acid Chemistry, vol. 1 (New York, New York: Academic Press, 1974),
page 7. (https://books.google.com/books?id=oAKAbV7FHfgC&pg=P A7#v=onepage&q&f=false)
Magnus (1844) "Ueber das Vorkommen von Xanthicoxyd imGuano" (https://books.google.com/books?id=nT49A
AAAcAAJ&pg=PA395#v=onepage&q&f=false) (On the occurrence of xanthic oxide in guano),Annalen der
Chemie und Pharmacie, 51 : 395-397.
B. Unger (1846) "Bemerkungen zu obiger Notiz"(https://books.google.com/books?id=7TU9AAAAcAAJ&pg=P A1
8#v=onepage&q&f=false)(Comments on the above notice),Annalen der Chemie und Pharmacie, 58 : 18-20.
From page 20: " … desshalb möchte ich den NamenGuanin vorschlagen, welcher an seine Herkunft erinnert."(
… therefore I would like to suggest the nameguanine, which is reminiscent of its origin.)
B. Unger (1846) "Das Guanin und seine Verbindungen" (https://books.google.com/books?id=AjY9AAAAcAAJ&pg
=PA58#v=onepage&q&f=false)(Guanine and its compounds),Annalen der Chemie und Pharmacie, 59 : 58-68.
4. "Emil Fischer - Biographical"(https://www.nobelprize.org/nobel_prizes/chemistry/laureates/1902/fischer-bio.html).
5. Levy, Matthew; Stanley L. Miller; John Oró (August 1999). "Production of Guanine from NH4CN Polymerizations".
Journal of Molecular Evolution. 49 (2): 165–8. doi:10.1007/PL00006539 (https://doi.org/10.1007%2FPL00006539).
PMID 10441668 (https://www.ncbi.nlm.nih.gov/pubmed/10441668). - quotes the Yuasa paper and cites the
possibility of there being a contaminant in the reaction.
6. Miyakawa, S; Murasawa, K.; Kobayashi, K.; Sawaoka, AB. (December 2000). "Abiotic synthesis of guanine with
high-temperature plasma".Orig Life Evol Biosph. 30 (6): 557–66. doi:10.1023/A:1026587607264(https://doi.org/10.1
023%2FA%3A1026587607264). PMID 11196576 (https://www.ncbi.nlm.nih.gov/pubmed/11196576).
7. OED. "guanine" and also "guano".
8. 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,pp. 64–65. (https://books.google.com/books?id=K2
mhGDwiSJsC&pg=PA64#v=onepage&q&f=false)
9. In 1861 the French chemist Charles-Louis Barreswil (1817–1870) found that "pearl essence" was guanine. See:
Barreswil (1861) "Sur le blanc d'ablette qui sert à la fabrication des perles fausses"(http://gallica.bnf.fr/ark:/12148/bp
t6k3010v/f246.item.zoom)(On the white of ablette that's used in making imitation pearls),Comptes rendus, 53 : 246.
10. Whitworth, Melissa (2008-10-16)."Geisha facial, the 'latest beauty secret' of V
ictoria Beckham, brought to the
masses" (https://www.telegraph.co.uk/fashion/beauty/3365670/Geisha-facial%2C-the-%27latest-beauty-secret%27-o
f-Victoria-Beckham%2C-brought-to-the-masses.html). Lifestyle. Telegraph. Retrieved 2008-11-20.
11. "How Pearls are Made...Faux, Fake, Imitation, Simulated or Man-made"
(http://www.karipearls.com/how-pearls-are-
made.html).
12. Gur, D., Palmer, B., Weiner, S., and Addadi, L. (2017)."Light manipulation by guanine crystals in organisms:
biogenic scatterers, mirrors, multilayer reflectors and photonic crystals"(http://onlinelibrary.wiley.com.ezproxy.library.
dal.ca/doi/10.1002/adfm.201603514/full). Advanced Functional Materials. 27 (6): 1603514.
doi:10.1002/adfm.201603514(https://doi.org/10.1002%2Fadfm.201603514)– via Wiley Online Library.
13. Fox, D.L. (1979). Biochromy, natural coloration of living things. University of California Press.ISBN 978-0-520-
03699-4.
14. 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" (http://www.pnas.org/conten
t/early/2011/08/10/1106493108). Proc. Natl. Acad. Sci. U.S.A. PNAS. 108: 13995–8. doi:10.1073/pnas.1106493108
(https://doi.org/10.1073%2Fpnas.1106493108) . PMC 3161613 (https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3161
613). PMID 21836052 (https://www.ncbi.nlm.nih.gov/pubmed/21836052). Retrieved 2011-08-15.
15. Steigerwald, John (8 August 2011)."NASA Researchers: DNA Building Blocks Can Be Made in Space"(http://www.n
asa.gov/topics/solarsystem/features/dna-meteorites.html)
. NASA. Retrieved 2011-08-10.
16. ScienceDaily Staff (9 August 2011). "DNA Building Blocks Can Be Made in Space, NASA Evidence Suggests"
(http
s://www.sciencedaily.com/releases/2011/08/110808220659.htm). ScienceDaily. Retrieved 2011-08-09.

External links
Guanine MS Spectrum
Guanine at chemicalland21.com

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