Condensation Approach to Aliphatic Oligourea Foldamers: Helices with  N ‐(Pyrrolidin‐2‐ylmethyl)ureido Junctions | Zendy

Fremaux Juliette | Zendy; Fischer Lucile | Zendy; Arbogast Thomas | Zendy; Kauffmann Brice | Zendy; Guichard Gilles | Zendy

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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.

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