guanine [key], organic base of the purine family. It was reported (1846) to be in the guano of birds; later (1879–84) it was established as one of the major constituents of nucleic acids. The accepted structure of the guanine molecule was proposed in 1875, and the compound was first synthesized in 1900. When combined with the sugar ribose in a glycosidic linkage, guanine forms a derivative called guanosine (a nucleoside), which in turn can be phosphorylated with from one to three phosphoric acid groups, yielding the three nucleotides GMP (guanosine monophosphate), GDP (guanosine diphosphate), and GTP (guanosine triphosphate). Analogous nucleosides and nucleotides are formed from guanine and deoxyribose. The nucleotide derivatives of guanine perform important functions in cellular metabolism. GTP acts as a coenzyme in carbohydrate metabolism and in the biosynthesis of proteins; it can readily donate one of its phosphate groups to adenosine diphosphate (ADP) to form adenosine triphosphate (ATP), an extremely important intermediate in the transfer of chemical energy in living systems. GTP is the source of the guanosine found in RNA and deoxyguanosine triphosphate (dGTP) is the source of the deoxyguanosine in DNA, and thus guanine is intimately involved in the preservation and transfer of genetic information. Guanine is said to account for the iridescence of fish scales and the white, shiny appearance of the skin of many amphibians and reptiles.
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