Summary
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.
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Abbreviations
- pG:
-
guanosine 5′-monophosphate
- pA:
-
adenosine 5′-monophosphate
- ImpG:
-
guanosine 5′-phosphorimidazolide
- ImpA:
-
adenosine 5′-phosphorimidazolide
- 2-MeImpG:
-
(guanosine 5′-phosphor)-2-methylimidazolide
- 2-MeImpA:
-
(adenosine 5′-phosphor)-2-methylimidazolide
- poly(C):
-
polycytidylic acid
- poly(U):
-
polyuridylic acid
- PRNase:
-
pancreatic ribonuclease
References
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Rodriguez, L., Orgel, L.E. Acceleration of the template-directed reactions of nucleoside 5′-phosphorimidazolides by acylation. J Mol Evol 32, 278–281 (1991). https://doi.org/10.1007/BF02102184
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DOI: https://doi.org/10.1007/BF02102184