Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2014, Issue 19, Pages 3971-3975Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201402040
Keywords
Amides; Solid-phase synthesis; Structure elucidation; Foldamers
Categories
Funding
- Carlsberg Foundation [2011_01_0432]
- Lundbeck Foundation
- Aase and Ejnar Danielsens Foundation
- Augustinus Foundation
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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.
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