Work

Energetics of an n → π* Interaction that Impacts Protein Structure

Year: 2006

Type: article

Abstract: [structure: see text] 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 (rho = 0.26) is indicative of a substantial effect. This effect arises from a favorable n --> pi interaction between the amide oxygen and ester carbonyl. In a polypeptide chain, an analogous interaction can stabilize the conformation of trans peptide bonds, alpha-helices, and polyproline type-II helices.

Source: Organic Letters

DOI: 10.1021/ol061569t

Authors: Jonathan A. Hodges, Ronald T. Raines

Institution: University of Wisconsin–Madison

Language: English

Topic: Protein Structure and Dynamics

Subfield: Molecular Biology

Field: Biochemistry, Genetics and Molecular Biology

Domain: Life Sciences

Open Access status: green

Funders: National Institutes of Health, National Institute of Arthritis and Musculoskeletal and Skin Diseases

Awards: Strand Invasion of the Collagen Triple Helix, Chemistry and Biology of Collagen, G6605776272, G688722168