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Article Dans Une Revue Beilstein Journal of Organic Chemistry Année : 2022

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

Maxime Pypec
Laurent Jouffret
Claude Taillefumier
Olivier Roy

Résumé

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 synthesized in solution using N -Boc- N -methylhydrazine as a peptoid submonomer and stepwise or segment coupling methodologies. Their structures were analyzed in solution by 1D and 2D NMR, in the solid state by X-ray crystallography (dimer 2 ), and implicit solvent QM geometry optimizations. 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 1 H NMR and the antiparallel arrangement of mirror image molecules held together via two hydrogen bonds in the crystal lattice of dimer 2 .

Domaines

Chimie

Dates et versions

hal-03807850 , version 1 (10-10-2022)

Identifiants

Citer

Maxime Pypec, Laurent Jouffret, Claude Taillefumier, Olivier Roy. First series of N -alkylamino peptoid homooligomers: solution phase synthesis and conformational investigation. Beilstein Journal of Organic Chemistry, 2022, 18, pp.845-854. ⟨10.3762/bjoc.18.85⟩. ⟨hal-03807850⟩
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