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Construction and Systematical Symmetric Studies of a Series of Supramolecular Clusters with Binary or Ternary Ammonium Triphenylacetates
Published on: February 15, 2016
Unveiling the conformational landscape of achiral all-cis tert-butyl β-peptoids
Gaetano Angelici1, Nicholus Bhattacharjee2, Maxime Pypec1
1Université Clermont Auvergne, Clermont Auvergne INP, CNRS, ICCF, 63000 Clermont-Ferrand, France. claude.taillefumier@uca.fr.
Abstract:
The synthesis and conformational study of N-substituted β-alanines with tert-butyl side chains is described. The oligomers prepared by submonomer synthesis and block coupling methods are up to 15 residues long and are characterised by amide bonds in the cis-conformation. A conformational study comprising experimental solution NMR spectroscopy, X-ray crystallography and molecular modeling shows that despite their intrinsic higher conformational flexibility compared to their α-peptoid counterparts, this family of achiral oligomers adopt preferred secondary structures including a helical conformation close to that described with (1-naphthyl)ethyl side chains but also a novel ribbon-like conformation.
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