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Increasing the Size of an Aromatic Helical Foldamer Cavity by Strand Intercalation
Author(s) -
Singleton Michael L.,
Pirotte Geert,
Kauffmann Brice,
Ferrand Yann,
Huc Ivan
Publication year - 2014
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201407752
Subject(s) - foldamer , intercalation (chemistry) , helix (gastropod) , crystallography , chemistry , monomer , stereochemistry , sequence (biology) , polymer , organic chemistry , biochemistry , ecology , snail , biology
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 ( K dim >10 7 M −1 ) by the shorter strand, when it was mixed with the single‐helical capsule sequence, a cross‐hybridized double helix was formed with K a >10 5 M −1 . 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 Å 3 .