First series of N-alkylamino peptoid homooligomers: Solution phase synthesis and conformational investigation

Submitting author affiliation:
Université Clermont-Auvergne, AUBIERE, France

Beilstein Arch. 2022, 202234.

Published 10 May 2022

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The synthesis and conformational analysis of the first series of peptoid oligomers composed of consecutive N-alkylamino glycine units is investigated. We demonstrate that N-methylamino glycine homooligomers can be readily synthesised in solution using N-Boc-N-methylhydrazine as a peptoid submonomer and stepwise or segment coupling methodologies. Their structures were analyzed in solution by 1-D and 2-D NMR, in the solid state by X-ray crystallography (dimer 2) and implicit solvent QM geometry optimisations. N-methylamino peptoids were found to preferentially adopt trans amide bonds with the side chain N-H bonds oriented approximately perpendicular to the amide plane. This orientation is conducive to local backbone stabilization through intra-residue hydrogen bonds but also to intermolecular associations. The high capacity of N-methylamino peptoids to establish intermolecular hydrogen bonds was notably deduced from pronounced concentration dependent N-H chemical shift variation in 1H-NMR, the antiparallel arrangement of mirror images molecules held together via two hydrogen bonds in the crystal lattice of dimer 2, and self-assembling properties of dimer 2 visualized by transmission electron microscopy.

Keywords: peptoid; cis/trans isomerism; trans-inducing side chain; structure

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PYPEC, M.; JOUFFRET, L.; TAILLEFUMIER, C.; ROY, O. Beilstein Arch. 2022, 202234. doi:10.3762/bxiv.2022.34.v1

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