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Incorporation of unprotected heterocyclic side chains into peptoid oligomers via solid-phase submonomer synthesis
Journal article   Peer reviewed

Incorporation of unprotected heterocyclic side chains into peptoid oligomers via solid-phase submonomer synthesis

Timothy S Burkoth, Aaron T Fafarman, Deborah H Charych, Michael D Connolly and Ronald N Zuckermann
Journal of the American Chemical Society, v 125(29), pp 8841-8845
23 Jul 2003
DOI: https://doi.org/10.1021/ja0352101
PMID: 12862480
Featured in Collection :   UN Sustainable Development Goals @ Drexel

Abstract

Acylation Biomimetic Materials - chemical synthesis Glycine - analogs & derivatives Glycine - chemical synthesis Imidazoles - chemical synthesis Imidazoles - chemistry Indoles - chemical synthesis Indoles - chemistry Peptides - chemical synthesis Peptides - chemistry Pyrazines - chemical synthesis Pyrazines - chemistry Pyridines - chemical synthesis Pyridines - chemistry Quinolines - chemical synthesis Quinolines - chemistry
Peptoids (N-substituted glycines) are an important class of biomimetic oligomers that have made a significant impact in the areas of combinatorial drug discovery, gene therapy, drug delivery, and biopolymer folding in recent years. Sequence-specific peptoid oligomers are easily assembled from primary amines by the solid-phase submonomer method. However, most amines that contain heterocyclic nitrogens in the side chain do not incorporate efficiently. We present here a straightforward revision of the submonomer method that allows efficient incorporation of unprotected imidazoles, pyridines, pyrazines, indoles, and quinolines into oligomers as long as 15 monomers in length. This improved method uses chloroacetic acid instead of bromoacetic acid in the acylation step of the monomer addition cycle, and allows for the incorporation of new side chains that should enable the synthesis of peptoids with entirely new properties.

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UN Sustainable Development Goals (SDGs)

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#3 Good Health and Well-Being

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Web of Science research areas
Chemistry, Multidisciplinary
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