Energetics of an n → π* Interaction that Impacts Protein Structure
- 22 September 2006
- journal article
- letter
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 8 (21) , 4695-4697
- https://doi.org/10.1021/ol061569t
Abstract
The trans/cis ratio of the amide bond in N-formylproline phenylesters correlates with electron withdrawal by a para substituent. The slope of the Hammett plot (ρ = 0.26) is indicative of a substantial effect. This effect arises from a favorable n → π* interaction between the amide oxygen and ester carbonyl. In a polypeptide chain, an analogous interaction can stabilize the conformation of trans peptide bonds, α-helices, and polyproline type-II helices.Keywords
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