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Electrostatic versus steric effects in peptidomimicry: Synthesis and secondary structure analysis of gramicidin S analogues with (E)-alkene peptide isosteres
Xiao, Jingbo,Weisblum, Bernard,Wipf, Peter
, p. 5742 - 5743 (2007/10/03)
A concise synthetic strategy was used for the first preparation of GS analogues with trisubstituted (E)-alkene peptide bond replacements. Solution and solid state conformational analysis demonstrated that the bistrifluoromethylated analogue was a superior mimic of the natural product, whereas the incorporation of methyl groups into the alkene peptide isostere led to a far greater perturbation of the secondary structure features of GS. The difference between CF3- and CH3-substitution can be explained by the superior electrostatic carbonyl group mimicry of the former function. Copyright
