Pseudopeptidic compounds for the generation of dynamic combinatorial libraries of chemically diverse macrocycles in aqueous media

A straightforward four-step synthesis leads to the preparation of C2-symmetric dithiols containing a central aromatic core and amino acid side chains. These building blocks allow the preparation of dynamic covalent libraries of pseudopeptidic macrocycles in aqueous media that cover a broad range of polarities, functional groups and bulkiness mirroring the diversity found in natural peptides. The versatility of the generated dynamic libraries has been illustrated by the amplification of two different members from the same library upon the action of two biologically relevant templates. © The Royal Society of ChemistryThis work was supported by the Spanish Ministry of Economy and Competitiveness (MINECO/FEDER, CTQ2012-38543-C03-03, CTQ2015-70117-R and CSIC13-4E-2076), EU (FP7-PEOPLE-2012-CIG-321659) and Generalitat de Catalunya (2014 SGR 231). Personal financial support for J. S. (MINECO, Ramon y Cajal contract) and J. A. (CSIC and European Social Fund, JAE-predoc fellowship) are gratefully acknowledged. We also thank Dr Yolanda Perez for the helpful assistance in the acquisition of the water-suppression NMR experiments.Peer reviewe