Properties
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 multiple tautomeric forms. For both the imidazole and pyrimidine rings, the proton can reside on either of the ring nitrogens. But a single tautomeric form dominates in nucleoside or nucleotide versions of guanine.2
Guanine 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 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.3
Guanine can be hydrolyzed with strong acid to glycine, ammonia, carbon dioxide, and carbon monoxide. First, guanine gets deaminated to become xanthine.4 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. Among the DNA/RNA bases, guanine has the lowest oxidation potential5 playing a key role in the oxidatively induced damage to nucleic acids. See main article guanine radical cations and DNA oxidation.
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 1846.6 Between 1882 and 1906, Emil Fischer determined the structure and also showed that uric acid can be converted to guanine.7
Synthesis
A Fischer–Tropsch synthesis can 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
Trace amounts of guanine form by the polymerization of ammonium cyanide (NH
4CN). Two experiments conducted by Levy et al. showed that heating 10 mol·L−1 NH
4CN at 80 °C for 24 hours gave a yield of 0.0007%, while using 0.1 mol·L−1 NH
4CN 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 NH
3, CH
4, C
2H
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.8
- 10NH3 + 2CH4 + 4C2H6 + 2H2O → 2C5H8N5O (guanine) + 25H2
Another possible abiotic route was explored by quenching a 90% N2–10%CO–H2O gas mixture high-temperature plasma.9
involves heating with for several hours.
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".11
In 1656 in Paris, a Mr. Jaquin extracted from the scales of the fish Alburnus alburnus so-called "pearl essence",12 which is crystalline guanine.13 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, because the guanine in the droppings makes the skin look paler.14 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),15 and and particles.
References
- 1Dawson, R.M.C., et al., Data for Biochemical Research, Oxford, Clarendon Press, 1959.
- 2Saenger, W. (1984). Principles of Nucleic Acid Structure. Springer Advanced Texts in Chemistry. Springer Science & Business Media. p. 112. doi:10.1007/978-1-4612-5190-3. ISBN 978-0-387-90761-1.
- 3"Base pairing". The Chinese University of Hong Kong. Retrieved 2026-06-12.
- 4Angstadt, Carol N (1997). "Purines and pyrimidines". utah.edu. Retrieved 2024-11-20.
- 5Palecek; Bartosik, M. (2012). "Electrochemistry of Nucleic Acids". Chem. Rev. 6: 3427–3481. doi:10.1021/cr200303p.
- 6Guanine was first isolated in 1844 by Julius Bodo Unger (1819–1885), a student of 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.
Magnus (1844) (On the occurrence of xanthic oxide in guano), , : 395-397. B. Unger (1846) (Comments on the above notice), , : 18-20. From page 20: Guanin ( ... therefore I would like to suggest the name , which is reminiscent of its origin.) B. Unger (1846) (Guanine and its compounds), , : 58-68.
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.16
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.16
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.181920
