Control of conformation in α-helix mimicking aromatic oligoamide foldamers through interactions between adjacent side-chains

Abstract

Hydrogen-bonding interactions are used to bias the conformation of an aromatic oligoamide foldamer in favour of an α-helix mimicking syn conformer.

Side Chain Regioisomers that Dictate Optical Properties and Mechanofluorochromism through Crystal Packing

“…As they are not coupled to the conjugated system, incorporating directional interactions into side chains enables structural control that is orthogonal to the function of the main chain and broadly applicable for many classes of main chain structures. − Analogous to the design in Chart , our group’s previous work has demonstrated side chain engineering for guiding optical and responsive properties in phenylene-ethynylenes (PEs) via electron-poor fluoroarene pendants that cofacially stack with arenes in the PE chromophore (ArF–ArH interactions). − This robust aromatic stacking interaction is useful in a variety of contexts to direct molecular packing. − To accommodate these interactions, the PE linkages twist out of coplanarity by at least 55°, reducing conjugation. In addition, these ArF–ArH interactions insulate the PE chromophores from each other by blocking regions of overlap that are otherwise required for through-space coupling.…”

Overcoming AlbD Protease Resistance and Improving Potency: Synthesis and Bioactivity of Antibacterial Albicidin Analogues with Amide Bond Isosteres

“…Our study on amide bond replacements encourages the application of these isosteres to replace not only other amides of albicidin or related cystobactamide structures 19−21 but also other peptide structures or aromatic oligoamides. 22,23 Whereas the (Z)-fluoroalkene ( 7) is a stateof-the-art well-known isostere, 24 to our knowledge, we report one of the very few examples 7 of an alkyne (5) considered to act as an amide isostere. 9 This Letter is a further important step in understanding the SARs of albicidin.…”

Cavity-containing aromatic oligoamide foldamers and macrocycles: progress and future perspectives

“…These short sequences are structurally defined and have tunable sidechains. 29 Wilson demonstrated that these short oligomers could interact with large protein structures and can even restore catalytic function to an RNase (responsible for RNA degradation) (Fig. 13).…”