Advances towards aromatic oligoamide foldamers: synthesis and X-ray structures of dimeric arylopeptoids with conformation-directing side chains
Research output: Contribution to journal › Journal article › Research › peer-review
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 language | English |
---|---|
Journal | European Journal of Organic Chemistry |
Volume | 2014 |
Issue number | 19 |
Pages (from-to) | 3971-3975 |
Number of pages | 5 |
ISSN | 1434-193X |
DOIs | |
Publication status | Published - 2014 |
- Amides, Foldamers, Solid-phase synthesis, Structure elucidation
Research areas
ID: 127672067