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Advances towards Aromatic Oligoamide Foldamers: Synthesis and X-ray Structures of Dimeric Arylopeptoids with Conformation-Directing Side Chains

Author:: Hjelmgaard, Thomas Plesner, Malene Dissing, Mette Marie Andersen, Jeanette Marker Frydenvang, Karla Nielsen, John
Journal:: EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Issue Date:: 2014
Abstract(summary):: 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.
Page:: 3971---3975

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Cited By

Rasmussen, Jakob Ewald, Boccia, Marcello Massimo, Nielsen, John, Taillefumier, Claude, Faure, Sophie, Hjelmgaard, Thomas. null[J]. TETRAHEDRON LETTERS,2014:5940---5943.

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Advances towards Aromatic Oligoamide Foldamers: Synthesis and X-ray Structures of Dimeric Arylopeptoids with Conformation-Directing Side Chains

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