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Issue 20, 2019
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Sequence information transfer using covalent template-directed synthesis

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Abstract

Template-directed synthesis is the biological method for the assembly of oligomers of defined sequence, providing the molecular basis for replication and the process of evolution. To apply analogous processes to synthetic oligomeric molecules, methods are required for the transfer of sequence information from a template to a daughter strand. We show that covalent template-directed synthesis is a promising approach for the molecular replication of sequence information in synthetic oligomers. Two monomer building blocks were synthesized: a phenol monomer and a benzoic acid monomer, each bearing an alkyne and an azide for oligomerization via copper catalyzed azide alkyne cycloaddition (CuAAC) reactions. Stepwise synthesis was used to prepare oligomers, where information was encoded as the sequence of phenol (P) and benzoic acid (A) units. Ester base-pairing was used to attach monomers to a mixed sequence template, and CuAAC was used to zip up the backbone. Hydrolysis of the ester base-pairs gave back the starting template and the sequence complementary copy. When the AAP trimer was used as the template, the complementary sequence PPA was obtained as the major product, with a small amount of scrambling resulting in PAP as a side-product. This covalent base-pairing strategy represents a general approach that can be implemented in different formats for the replication of sequence information in synthetic oligomers.

Graphical abstract: Sequence information transfer using covalent template-directed synthesis

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Supplementary files

Article information


Submitted
25 Mar 2019
Accepted
22 Apr 2019
First published
26 Apr 2019

This article is Open Access
All publication charges for this article have been paid for by the Royal Society of Chemistry

Chem. Sci., 2019,10, 5258-5266
Article type
Edge Article

Sequence information transfer using covalent template-directed synthesis

D. Núñez-Villanueva, M. Ciaccia, G. Iadevaia, E. Sanna and C. A. Hunter, Chem. Sci., 2019, 10, 5258
DOI: 10.1039/C9SC01460H

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