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Template-directed Nonenzymatic Primer Extension Using 2-methylimidazole-activated Morpholino Derivatives of Guanosine and Cytidine.

著者 Zhang W , Pal A , Ricardo A , Szostak JW
J Am Chem Soc.2019 Jul 12 ; ():.
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Efforts to develop self-replicating nucleic acids have led to insights into the origin of life, and have also suggested potential pathways to the design of artificial life forms based on non-natural nucleic acids. The template-directed nonenzymatic polymerization of activated ribonucleotide monomers is generally slow because of the relatively weak nucleophilicity of the primer 3'-hydroxyl. To circumvent this problem, several nucleic acids based on amino-sugar nucleotides have been studied, and as expected the more nucleophilic amine generally results in faster primer extension. Extending this logic, we have chosen to study morpholino nucleic acid (MoNA), because the secondary amine of the morpholino nucleotides is expected to be highly nucleophilic. We describe the synthesis of 2-methylimidazole activated MoNA monomers from their corresponding ribonucleoside 5'-monophosphates, and the synthesis of an RNA primer with a terminal MoNA nucleotide. We show that the activated G and C MoNA monomers enable rapid and efficient extension of the morpholino-terminated primer on homopolymeric and mixed-sequenced RNA templates. Our results show that MoNA is a non-natural informational polymer that is worthy of further study as a candidate self-replicating material.
PMID: 31298852 [PubMed - as supplied by publisher]
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