Control of Helix Screw‐Sense Preference in Dynamic Foldamers of meso Symmetry Built From Chiral Monomeric Units
Abstract
Meso oligoureas are dynamic hydrogen-bonded foldamers capable of reversible helix polarity inversion but have so far been limited to symmetrical meso-cyclohexane-1,2-diamine monomeric units, limiting both sequence diversity and structural modification. Here, we report the synthesis and characterization of meso and "near-meso" oligoureas assembled exclusively from chiral units, thereby expanding the accessible sequence space. Despite their overall symmetry, meso oligoureas display sequence-dependent helix-forming propensities. Controlled desymmetrization of terminal groups induces a preferred helix screw-sense, while binding of achiral hydrogen-bond acceptors reverses the directionality of the intramolecular hydrogen-bonding network, leading to sequence-dependent screw-sense inversion. Structural, spectroscopic, and solution studies consistently support this stimulus-responsive folding behavior.
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BibTeX
@article{gupta2026control,
title = {{Control of Helix Screw‐Sense Preference in Dynamic Foldamers of meso Symmetry Built From Chiral Monomeric Units}},
author = {Naveen Gupta and Mégane Bornerie and Bo Li and Antoine Hacihasanoglu and Orlando Villegas Bello and Stéphanie Antunes and Estelle Morvan and Jean‐marc Sotiropoulos and Philippe Carbonnière and Morgane Pasco and Brice Kauffmann and Céline Douat and Sung Hyun Yoo and Gilles Guichard},
journal = {Angewandte Chemie International Edition},
year = {2026},
month = oct,
doi = {10.1002/anie.6601433},
url = {https://hal.science/hal-05799032v1},
note = {CC BY-NC-SA 4.0},
}
RIS
TY - JOUR
TI - Control of Helix Screw‐Sense Preference in Dynamic Foldamers of meso Symmetry Built From Chiral Monomeric Units
AU - Naveen Gupta
AU - Mégane Bornerie
AU - Bo Li
AU - Antoine Hacihasanoglu
AU - Orlando Villegas Bello
AU - Stéphanie Antunes
AU - Estelle Morvan
AU - Jean‐marc Sotiropoulos
AU - Philippe Carbonnière
AU - Morgane Pasco
AU - Brice Kauffmann
AU - Céline Douat
AU - Sung Hyun Yoo
AU - Gilles Guichard
PY - 2026
DA - 2026/10/07
JO - Angewandte Chemie International Edition
DO - 10.1002/anie.6601433
UR - https://hal.science/hal-05799032v1
AB - Meso oligoureas are dynamic hydrogen-bonded foldamers capable of reversible helix polarity inversion but have so far been limited to symmetrical meso-cyclohexane-1,2-diamine monomeric units, limiting both sequence diversity and structural modification. Here, we report the synthesis and characterization of meso and "near-meso" oligoureas assembled exclusively from chiral units, thereby expanding the accessible sequence space. Despite their overall symmetry, meso oligoureas display sequence-dependent helix-forming propensities. Controlled desymmetrization of terminal groups induces a preferred helix screw-sense, while binding of achiral hydrogen-bond acceptors reverses the directionality of the intramolecular hydrogen-bonding network, leading to sequence-dependent screw-sense inversion. Structural, spectroscopic, and solution studies consistently support this stimulus-responsive folding behavior.
SN - 1433-7851
SN - 1521-3773
ER -