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Issue 46, 2020
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Sequence-defined l-glutamamide oligomers with pendant supramolecular motifs via iterative synthesis and orthogonal post-functionalization

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Abstract

One of the great challenges in polymer chemistry is to achieve discrete and sequence-defined synthetic polymers that fold in defined conformations and form well-defined three-dimensional structures. Here, we present our progress to arrive at functional, sequence-defined and discrete oligomers by selecting a synthetic approach based on oligo-L-glutamamides. We introduce a solution-based iterative approach and start with an orthogonally protected L-glutamic acid derivative with an alkene or alkyne side chain. Using subsequent deprotection, activation and coupling steps, discrete, sequence-defined octamers were prepared with alkene or alkyne pendants at defined positions. Benzene-1,3,5-tricarboxamide (BTA) was selected as the supramolecular motif and decyl side chains for enhancing solubility. Full functionalization of the octamer was achieved with subsequent Cu(I)-catalyzed alkyne–azide and thiol–ene “click” chemistry, affording octamers with two BTA motifs at pre-defined positions. The octamers show a strong propensity to form hydrogen bonds in bulk as evidenced by infrared spectroscopy. In dilute solution, intermolecular aggregation of the amides present in the backbone and/or BTAs is observed. Our work shows that the iterative method serves as an reliable strategy for the synthesis of functionalized sequence-defined, discrete oligomers comprising side chain supramolecular motifs, although further optimizations are required.

Graphical abstract: Sequence-defined l-glutamamide oligomers with pendant supramolecular motifs via iterative synthesis and orthogonal post-functionalization

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Supplementary files

Article information


Submitted
13 Aug 2020
Accepted
01 Nov 2020
First published
02 Nov 2020

This article is Open Access

Polym. Chem., 2020,11, 7393-7401
Article type
Paper

Sequence-defined L-glutamamide oligomers with pendant supramolecular motifs via iterative synthesis and orthogonal post-functionalization

M. L. Ślęczkowski, I. Segers, Y. Liu and A. R. A. Palmans, Polym. Chem., 2020, 11, 7393
DOI: 10.1039/D0PY01157F

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