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Condensation Approach to Aliphatic Oligourea Foldamers: Helices with N ‐(Pyrrolidin‐2‐ylmethyl)ureido Junctions
Author(s) -
Fremaux Juliette,
Fischer Lucile,
Arbogast Thomas,
Kauffmann Brice,
Guichard Gilles
Publication year - 2011
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201105416
Subject(s) - pyrrolidine , chemistry , folding (dsp implementation) , helix (gastropod) , crystallography , condensation , stereochemistry , physics , thermodynamics , ecology , snail , electrical engineering , biology , engineering
Caught in a fold : A simple and efficient coupling strategy to make aliphatic oligourea foldamers is reported. Crystal structures show that the pyrrolidine units (red; see picture) do not impair the 2.5‐helical folding of the oligoureas. This modular strategy enables assembly of long helical segments containing non‐adjacent pyrrolidine units as exemplified by the synthesis of a helix that is approximately 40 Å long.