Membrane adsorption and binding, cellular uptake and cytotoxicity of cell-penetrating peptidomimetics with α-peptide/β-peptoid backbone: Effects of hydrogen bonding and α-chirality in the β-peptoid residues

► Novel proteolytically stable peptidomimetics with α-peptide/β-peptoid structure exhibit promising cell-penetrating potential. ► Hydrogen bonding determined by molecular simulations reflects the level of membrane adsorption and cellular uptake. ► α-chirality stabilizes the folded conformation of the peptidomimetics upon interaction with bilayer membranes. ► α-chirality in the β-peptoid residue correlate with higher levels of membrane adsorption and cellular uptake.