ja051002s_si_003.pdf (6.06 MB)
Electrostatic versus Steric Effects in Peptidomimicry: Synthesis and Secondary Structure Analysis of Gramicidin S Analogues with (E)-Alkene Peptide Isosteres
journal contribution
posted on 2005-04-27, 00:00 authored by Jingbo Xiao, Bernard Weisblum, Peter WipfA 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.
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carbonyl group mimicrybistrifluoromethylated analoguePeptidomimicrystructure featuresCH 3AlkenePeptideSteric EffectsstrategyIsosterefunctiontrisubstitutedCF 3perturbationincorporationsubstitutionmethyl groupsreplacementsolutionanalysisGS analoguespreparationalkene peptide isostereElectrostaticSecondary Structure AnalysisGramicidin S AnaloguesSynthesibond
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