Discrete sequence-defined oligomers are synthetic mimics of short peptides, with possible applications in multifunctional catalysis, information storage, drug delivery or self-assembly. Although different synthetic methodologies towards sequence-defined oligomers have been proposed, most of them fall short of peptide synthesis, either because they do not control the stereochemistry of the chains, or because they are restricted in the range of functional groups which can be installed on the chains. Here, we report on a new efficient synthetic strategy based on an iterative exponential growth (IEG) methodology, leading to stereocontrolled and sequence-defined oligomers incorporating a large range of functional groups (Scheme 1). The functional monomer units are obtained by the opening of the epoxide ring of an alkynyl-protected stereospecific glycidyl propargyl ether precursor, followed by the copper-catalyzed azide-alkyne cycloaddition (CuAAC) “click”reaction between the so-generated azide 9(R/S) and various functional groups bearing terminal alkyne handles (1-8). The resulting hydroxyl group of the monomers is then activated by 4-nitrophenyl chloroformate and connected through a carbamate bond to a 3-azidopropylamine spacer. These building blocks can then be linked together by releasing the terminal alkyne of one unit and clicking it with the azide group of another unit; using an IEG process gives rapid and efficient access to enantiopure oligomers containing up to eight monomer units. The composition, sequence and chirality of the discrete multifunctional oligomers were confirmed by 1H NMR, MS/MS and circular dichroism. We are now exploring the use of this strategy for the design of sequence-defined oligomers capable of self-assembly and catalysis.

Synthesis of sequence-defined and stereocontrolled discrete multifunctional oligomers

Macromolecular Chemistry: The Second Century

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ACS Spring 2020 National Meeting & Expo

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