
Solid-Phase Synthesis of Sequence-Defined Informational Oligomers
Author(s) -
Kyle R. Strom,
Jack W. Szostak
Publication year - 2020
Publication title -
journal of organic chemistry
Language(s) - Uncategorized
Resource type - Journals
SCImago Journal Rank - 1.2
H-Index - 228
eISSN - 1520-6904
pISSN - 0022-3263
DOI - 10.1021/acs.joc.0c01977
Subject(s) - monomer , intermolecular force , pairing , sequence (biology) , combinatorial chemistry , dynamic covalent chemistry , solid phase synthesis , covalent bond , chemistry , polymer , molecular recognition , phase (matter) , computer science , materials science , molecule , organic chemistry , supramolecular chemistry , biochemistry , physics , peptide , superconductivity , quantum mechanics
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.