Advances towards aromatic oligoamide foldamers: synthesis and X-ray structures of dimeric arylopeptoids with conformation-directing side chains

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Thomas Hjelmgaard, Malene Plesner, Mette Marie Dissing, Jeanette Marker Andersen, Karla Andrea Frydenvang, John Nielsen

We have efficiently synthesized 36 arylopeptoid dimers with ortho-, meta-, and para-substituted aromatic backbones and tert-butyl or phenyl side chains. The dimers were synthesized by using a "submonomer method" on solid phase, by applying a simplified common set of reaction conditions. X-ray crystallographic analysis of two of these dimers disclosed that the tert-butyl side chain invokes a cis amide conformation with a comparatively more closely packed structure of the surrounding aromatic backbone while the phenyl side chain results in a trans amide conformation with a more open, extended structure of the surrounding aromatic backbone. Investigation of the X-ray structures of two arylopeptoid dimers disclosed that the tert-butyl side chain invokes a cis amide conformation with a closely packed structure of the surrounding aromatic backbone while the phenyl side chain results in a trans amide conformation with a more open, extended structure of the surrounding aromatic backbone.

Original languageEnglish
JournalEuropean Journal of Organic Chemistry
Volume2014
Issue number19
Pages (from-to)3971-3975
Number of pages5
ISSN1434-193X
DOIs
Publication statusPublished - 2014

    Research areas

  • Amides, Foldamers, Solid-phase synthesis, Structure elucidation

ID: 127672067