Guanine

Guanine (/ˈɡwɑːnɪn/; or G, Gua) is one of the four main

nucleobases found in the nucleic acids DNA and RNA, the others Guanine
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
Names
Properties
IUPAC name
History 2-amino-9H-purin-6(1H)-one
Syntheses Other names
Biosynthesis 1,9-dihydro-6H-purin-6-one,
Other occurrences and biological uses 2-amino-6-hydroxypurine,
2-aminohypoxanthine,
See also
Guanine
References
Identifiers
External links
CAS Number 73-40-5 (http://www.c
ommonchemistry.org/
Properties ChemicalDetail.asp
x?ref=73-40-5)
Guanine, along with adenine and cytosine, is present in both DNA 3D model keto form: Interactive
and RNA, whereas thymine is usually seen only in DNA, and uracil (JSmol)
image (https://chema
only in RNA. Guanine has two tautomeric forms, the major keto
pps.stolaf.edu/jmol/j
form (see figures) and rare enol form.
mol.php?model=c1%
It binds to cytosine through three hydrogen bonds. In cytosine, the 5BnH%5Dc2c%28n
amino group acts as the hydrogen bond donor and the C-2 carbonyl 1%29c%28%3DO%2
and the N-3 amine as the hydrogen-bond acceptors. Guanine has the 9nc%28n2%29N)
C-6 carbonyl group that acts as the hydrogen bond acceptor, while a
enol form: Interactive
group at N-1 and the amino group at C-2 act as the hydrogen bond
image (https://chema
donors.
pps.stolaf.edu/jmol/j
mol.php?model=c1%
5BnH%5Dc2c%28n
1%29c%28O%29n
c%28n2%29N)
Beilstein 147911
Reference
ChEBI CHEBI:16235 (http
s://www.ebi.ac.uk/ch
ebi/searchId.do?cheb
iId=16235)
ChEMBL ChEMBL219568 (htt
ps://www.ebi.ac.uk/c
hembldb/index.php/c
ompound/inspect/Ch
EMBL219568)
ChemSpider 744 (http://www.che
mspider.com/Chemic
al-Structure.744.htm
l)
DrugBank DB02377 (https://ww
w.drugbank.ca/drugs/
DB02377)
ECHA 100.000.727 (https://
InfoCard echa.europa.eu/subs
tance-information/-/s
ubstanceinfo/100.00
0.727)
EC Number 200-799-8
Gmelin 431879
Reference
IUPHAR/BPS 4556 (http://www.gui
detopharmacology.or
g/GRAC/LigandDispl
ayForward?tab=sum
mary&ligandId=4556)
KEGG C00242 (https://www.
kegg.jp/entry/C0024
2)
PubChem 135398634 (https://p
CID
ubchem.ncbi.nlm.nih.
gov/compound/1353
98634)
RTECS MF8260000
number
UNII 5Z93L87A1R (https://
fdasis.nlm.nih.gov/sr
s/srsdirect.jsp?regno
=5Z93L87A1R)
CompTox DTXSID9052476 (htt
Dashboard ps://comptox.epa.go
(EPA) v/dashboard/DTXSID
9052476)

InChI
InChI=1S/C5H5N5O/c6-5-9-3-2(4(11)10-5)7-1
-8-3/h1H,(H4,6,7,8,9,10,11)
Key: UYTPUPDQBNUYGX-UHFFFAOYSA-N

InChI=1/C5H5N5O/c6-5-9-3-2(4(11)10-5)7-1-8
-3/h1H,(H4,6,7,8,9,10,11)
Key: UYTPUPDQBNUYGX-UHFFFAOYAE

SMILES
keto form: c1[nH]c2c(n1)c(=O)nc(n2)N

enol form: c1[nH]c2c(n1)c(O)nc(n2)N

Properties
Chemical C5H5N5O
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
(fire diamond) 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

Cytosine Guanine
Cytosine and guanine with the direction of hydrogen bonding indicated (arrow points positive to negative charge)

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 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.[3] Between 1882 and 1906, Fischer determined
the structure and also showed that uric 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% N2–10%CO–H2O gas mixture high-
temperature plasma.[6]
Traube's synthesis involves heating 2,4,5-triamino-1,6-dihydro-6-oxypyrimidine (as the sulfate) with formic

acid for several hours.

Biosynthesis
Guanine is not synthesized de novo, instead it's split from more complex molecule, guanosine, by the
enzyme guanosine phosphorylase:

guanosine + phosphate guanine + alpha-D-ribose 1-phosphate

Other occurrences and 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 guano, forming a constituent of the excrement of birds".[7]

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 are mica, 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 of deep-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 DNA and RNA (guanine, adenine and related organic molecules) may have
been formed extra-terrestrially in outer space.[14][15][16]

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
=PA7#v=onepage&q&f=false)
Magnus (1844) "Ueber das Vorkommen von Xanthicoxyd im Guano" (https://books.google.
com/books?id=nT49AAAAcAAJ&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=7TU9
AAAAcAAJ&pg=PA18#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
Namen Guanin vorschlagen, welcher an seine Herkunft erinnert." ( … therefore I would like
to suggest the name guanine, which is reminiscent of its origin.)
B. Unger (1846) "Das Guanin und seine Verbindungen" (https://books.google.com/books?i
d=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/190
2/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.
Bibcode:1999JMolE..49..165L (https://ui.adsabs.harvard.edu/abs/1999JMolE..49..165L).
doi:10.1007/PL00006539 (https://doi.org/10.1007%2FPL00006539). PMID 10441668 (https://p
ubmed.ncbi.nlm.nih.gov/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.
Bibcode:2000OLEB...30..557M (https://ui.adsabs.harvard.edu/abs/2000OLEB...30..557M).
doi:10.1023/A:1026587607264 (https://doi.org/10.1023%2FA%3A1026587607264).
PMID 11196576 (https://pubmed.ncbi.nlm.nih.gov/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=K2mhGDwiSJsC&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/bpt6k3010v/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 Victoria Beckham,
brought to the masses" (https://www.telegraph.co.uk/fashion/beauty/3365670/Geisha-facial%2
C-the-%27latest-beauty-secret%27-of-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, Dvir; Palmer, Benjamin A.; Weiner, Steve; Addadi, Lia (2017). "Light manipulation by
guanine crystals in organisms: biogenic scatterers, mirrors, multilayer reflectors and photonic
crystals". Advanced Functional Materials. 27 (6): 1603514. doi:10.1002/adfm.201603514 (http
s://doi.org/10.1002%2Fadfm.201603514).
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/content/early/2011/08/10/1106493108).
Proc. Natl. Acad. Sci. U.S.A. PNAS. 108 (34): 13995–8. Bibcode:2011PNAS..10813995C (http
s://ui.adsabs.harvard.edu/abs/2011PNAS..10813995C). doi:10.1073/pnas.1106493108 (http
s://doi.org/10.1073%2Fpnas.1106493108). PMC 3161613 (https://www.ncbi.nlm.nih.gov/pmc/a
rticles/PMC3161613). PMID 21836052 (https://pubmed.ncbi.nlm.nih.gov/21836052). Retrieved
2011-08-15.
15. Steigerwald, John (8 August 2011). "NASA Researchers: DNA Building Blocks Can Be Made
in Space" (http://www.nasa.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" (https://www.sciencedaily.com/releases/2011/08/110808220659.htm).
ScienceDaily. Retrieved 2011-08-09.

External links
Guanine MS Spectrum (http://gmd.mpimp-golm.mpg.de/Spectrums/d84fcceb-5982-470a-a0d5
-03450fb8aa47.aspx)
Guanine (http://www.chemicalland21.com/lifescience/phar/GUANINE.htm) at
chemicalland21.com

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