Increasing the size of an aromatic helical foldamer cavoty by strand intercalation
(2014) Angewandte Chemie (International Edition) — Vol. 53, p. 13140-13144 (2014)
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- Authors
- Abstract
- The postsynthetic modulation of capsules based on helical aromatic oligoamide foldamers would be a powerful approach for controlling their receptor properties without altering the initial monomer sequences. With the goal of developing a method to increase the size of a cavity within a helix, a single-helical foldamer capsule was synthesized with a wide-diameter central segment that was designed to intercalate with a second shorter helical strand. Despite the formation of stable double-helical homodimers (Kdim> 107m1) by the shorter strand, when it was mixed with the single-helical capsule sequence, a cross-hybridized double helix was formed with Ka>105m1. This strategy makes it possible to direct the formation of double-helical heterodimers. On the basis of solution- and solid-state structural data, this intercalation resulted in an increase in the central-cavity size to give a new interior volume of approximately 150 3.
- Affiliations
Université de Bordeaux (France) Institut Européen de Chime et Biologie
Citations
Singleton, M., Pirotte, G., Kauffmann, B., & Huc, I. (2014). Increasing the size of an aromatic helical foldamer cavoty by strand intercalation. Angewandte Chemie (International Edition), 53, 13140-13144. https://doi.org/10.1002/anie.201407752 (Original work published 2014)