Encoded combinatorial chemistry: A tool for the study of selective intermolecular interactions

This thesis presents examples for applying encoded combinatorial chemistry to trace molecular interactions between hosts and guests that could have not been predicted by conventional means.; In the first part the development of a class of new macrobicyclic two-armed receptors that bind certain tripeptides with extremely high sequence selectivity in organic solvents is described. These two-armed receptors have been the basis for the design of receptor libraries and have also found application in the separation of peptides and other small molecules on chiral stationary phases.; The second part discusses aspects of molecular recognition in water. Certain peptides have been found to bind with amazingly high selectivity to simple hydrophilic dye molecules and a novel dipeptide binding motif for {dollar}beta{dollar}-cyclodextrin has been discovered. In the latter experiments NMR-studies and molecular modelling gave a rationale for this selective interaction between {dollar}beta{dollar}-cyclodextrin and the peptide.