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

作者：Hjelmgaard Thomas^*; Plesner Malene; Dissing Mette Marie; Andersen Jeanette Marker; Frydenvang Karla; Nielsen John

来源：European Journal of Organic Chemistry, 2014, 2014(19): 3971-3975.

DOI：10.1002/ejoc.201402040

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

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.

• 出版日期2014-7