title: The prebiotic synthesis of modified purines and their potential role in the RNA world.
abstract: Modified purines are found in all organisms in the tRNA, rRNA, and even DNA, raising the possibility of an early role for these compounds in the evolution of life. These include N6-methyladenine, 1-methyladenine, N6,N6-dimethyladenine, 1-methylhypoxanthine, 1-methylguanine, and N2-methylguanine. We find that these bases as well as a number of nonbiological modified purines can be synthesized from adenine and guanine by the simple reaction of an amine or an amino group with adenine and guanine under the concentrated conditions of the drying-lagoon or drying-beach model of prebiotic synthesis with yields as high as 50%. These compounds are therefore as prebiotic as adenine and guanine and could have played an important role in the RNA world by providing additional functional groups in ribozymes, especially for the construction of hydrophobic binding pockets.
authors.affiliation: Department of Chemistry and Biochemistry, University of California, San Diego, La Jolla, CA 92093-0506, USA.
authors.forename: M
authors.initials: M
authors.lastname: Levy
authors.forename: S L
authors.initials: SL
authors.lastname: Miller
mesh_terms: D000225:Adenine / Q000031:analogs & derivatives* / Q000096:biosynthesis / Q000138:chemical synthesis / Q000737:chemistry; D000241:Adenosine / Q000031:analogs & derivatives* / Q000096:biosynthesis / Q000138:chemical synthesis; D000588:Amines / Q000737:chemistry; D000596:Amino Acids / Q000737:chemistry; D006147:Guanine / Q000737:chemistry; D006863:Hydrogen-Ion Concentration; D006868:Hydrolysis; D019271:Hypoxanthine / Q000737:chemistry / Q000378:metabolism; D007042:Hypoxanthines / Q000737:chemistry / Q000378:metabolism; D011687:Purines / Q000096:biosynthesis / Q000138:chemical synthesis; D012313:RNA / Q000737:chemistry* / Q000378:metabolism*; D013696:Temperature
chemical_list: D000225:Adenine; D000241:Adenosine; D000588:Amines; D000596:Amino Acids; D006147:Guanine; D019271:Hypoxanthine; D007042:Hypoxanthines; D011687:Purines; D012313:RNA; C026138:1-methylhypoxanthine; C010223:N-methyladenosine; C000730567:6-methyladenine