Solid-Phase Synthesis of Sequence-Defined Informational Oligomers

Genetic biopolymers utilize defined sequences and monomer-specific molecular recognition to store and transfer information. Synthetic polymers that mimic these attributes using reversible covalent chemistry for base-pairing pose unique synthetic challenges. Here, we describe a solid-phase synthesis...

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Bibliographic Details
Published in:Journal of organic chemistry 2020-11, Vol.85 (21), p.13929-13938
Main Authors: Strom, Kyle R, Szostak, Jack W
Format: Article
Language:English
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Summary:Genetic biopolymers utilize defined sequences and monomer-specific molecular recognition to store and transfer information. Synthetic polymers that mimic these attributes using reversible covalent chemistry for base-pairing pose unique synthetic challenges. Here, we describe a solid-phase synthesis methodology for the efficient construction of ethynyl benzene oligomers with specific sequences of aniline and benzaldehyde subunits. Handling these oligomers is complicated by the fact that they often exhibit multiple conformations because of intra- or intermolecular pairing. We describe conditions that allow the dynamic behavior of these oligomers to be controlled so that they may be manipulated and characterized without needing to mask the recognition units with protecting groups.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.0c01977