Fluorine's unique ability to participate in a number of subtle stereoelectronic effects has prompted its use as a tool to control the conformation of peptide analogs. The conformational energies of model �-amino acid peptides, and their fluorinated analogs, have been explored using a combination of correlated wave function and density functional theory calculations. Results from a variety of methods including ?B97X-D/cc-pVTZ, b3lyp/6-311++G**, and M062X/cc-pVTZ are compared to benchmark results from coupled-cluster calculations (CCSD(T)) employing complete basis set (CBS) extrapolation methods. The impact of aqueous solvation on the conformational profiles is also examined via a continuum solvation model. These results contribute to a better understanding of the impact of selective fluorination on the conformational preferences of model peptide mimics.

Conformational influence of fluorine substitution on peptides derived from β-amino acids

245th National Meeting (2013)

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