URUSHIBARA, Ko; FERRAND, Yann; LIU, Zhiwei; KATAGIRI, Kosuke; KAWAHATA, Masatoshi; MORVAN, Estelle; D'ELIA, Ryan; POPHRISTIC, Vojislava; TANATANI, Aya; HUC, Ivan

doi:10.1002/chem.202101201

URUSHIBARA, Ko
Chimie et Biologie des Membranes et des Nanoobjets [CBMN]

FERRAND, Yann

Chimie et Biologie des Membranes et des Nanoobjets [CBMN]

LIU, Zhiwei

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Article de revue

Ce document a été publié dans

Chemistry (Weinheim an der Bergstrasse, Germany). 2021 n° 27, p. 1-12

Résumé en anglais

The alkylation of some secondary amide functions with a dimethoxybenzyl (DMB) group in oligomers of 8-amino-2-quinolinecarboxylic acid destabilizes the otherwise favored helical conformations, and allows for cyclization to take place. A cyclic hexamer and a cyclic heptamer were produced in this manner. After DMB removal, X-ray crystallography and NMR show that the macrocycles adopt strained conformations that would be improbable in noncyclic species. The high helix folding propensity of the main chain is partly expressed in these conformations, but it remains frustrated by macrocyclization. Despite being homomeric, the macrocycles possess inequivalent monomer units. Experimental and computational studies highlight specific fluxional pathways within these structures. Extensive simulated annealing molecular dynamics allow for the prediction of the conformations for larger macrocycles with up to sixteen monomers.< Réduire

Mots clés en anglais

cis amide

fluxionality

foldamer

macrocycle

strained structures

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https://oskar-bordeaux.fr/handle/20.500.12278/95022

DOI

http://dx.doi.org/10.1002/chem.202101201

Unités de recherche

CBMN : Chimie & de Biologie des Membranes & des Nano-objets - UMR 5248

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Accessing Improbable Foldamer Shapes with Strained Macrocycles

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