Research output: Contribution to journal › Article › peer-review
Rossana Fanelli, Dénes Berta, Tamás Földes, Edina Rosta, Robert Andrew Atkinson, Hans-Jörg Hofmann, Kenneth Shankland, Alexander J A Cobb
Original language | English |
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Pages (from-to) | 1382-1393 |
Number of pages | 12 |
Journal | Journal of the American Chemical Society |
Volume | 142 |
Issue number | 3 |
Early online date | 10 Dec 2019 |
DOIs | |
Accepted/In press | 10 Dec 2019 |
E-pub ahead of print | 10 Dec 2019 |
Published | 22 Jan 2020 |
Additional links |
Organocatalytic Access to a_FANELLI_Publishedonline10December2019_GREEN AAM
Final_foldamers_article.pdf, 2.8 MB, application/pdf
Uploaded date:22 Jan 2020
Version:Accepted author manuscript
In this study, we have developed a highly enantioselective organocatalytic route to the (1S,2R)-2-(aminomethyl)cyclopentane-1-carboxylic acid monomer precursor, which has a cis-configuration between the C- and N-termini around the cyclopentane core. Kinetic measurements show that the product distribution changes over time due to epimerization of the C1 center. Computations suggest the cis-selectivity is a result of selective C-C bond formation, while subsequent steps appear to influence the selectivity at higher temperature. The resulting γ-amino acid residue was incorporated into a novel γ/α-peptide, which forms a well-ordered 10/12-helix with alternate H-bond directionality in spite of the smallest value of the ζ-angle yet observed for a helix of this type. This highly defined structure is also a result of the narrow range of potential ζ-angles in our monomer. In contrast, the larger range of potential ζ-values observed for the corresponding trans-system can be fulfilled by several competing helical structures.
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