Acceleration of the template-directed reactions of nucleoside 5'-phosphorimidazolides by acylation.
Nucleoside-5'-phosphorimidazolides react readily with acylating agents to give N-substituted products that are highly activated. In most cases these acylated derivatives undergo rapid hydrolysis to give nucleoside 5'-phosphates, whether or not a complementary template is present. However, guanosine 5'-phosphorimidazolide reacts with diethyl pyrocarbonate to give a derivative that oligomerizes rapidly and efficiently in the presence of polycytidylic acid and Pb2+. The reaction is complete in about 1 h, whereas the corresponding reaction in the absence of an acylating agent takes several days. However, the final yield of long oligomers is lower when diethyl pyrocarbonate is present.
Rodriguez
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Salk Institute for Biological Studies, San Diego, CA 92186-5800.
Orgel
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D000215:Acylation; D000249:Adenosine Monophosphate / Q000031:analogs & derivatives* / Q000737:chemistry; D004047:Diethyl Pyrocarbonate; D006157:Guanosine Monophosphate / Q000031:analogs & derivatives* / Q000737:chemistry; D006868:Hydrolysis; D007700:Kinetics; D011066:Poly C
C010671:adenosine 5'-phosphoroimidazolide; D011066:Poly C; C041881:adenosine 5'-phospho-2-methylimidazolide; D000249:Adenosine Monophosphate; C025339:guanosine 5'-phosphoimidazolide; C036896:guanosine 5'-phospho-2-methylimidazolide; D006157:Guanosine Monophosphate; D004047:Diethyl Pyrocarbonate