Guanine
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Overview
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.
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.
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.
- 5NH3 + CH4 + 2C2H6 + H2O → C5H8N5O (guanine) + (25/2)H2
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:
- 5CO + (1/2)H2 + 5NH3 → C5H8N5O (guanine) + 4H2O
Traube's synthesis involves heating 2,4,5-triamino-1,6-dihydro-6-oxypyrimidine (as the sulphate) with formic acid for several hours.
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.
See also
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. <br\> 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. <br\> 3. Lister, J.H. "Part II Purines." The Chemistry of Heterocyclic Compounds. Wiley-Interscience (New York). 1971.