Organic & Biomolecular Chemistry
Peptide cyclisation promoted by supramolecular complex formation

Arnout P. T. Hartendorp, Felix J. de Zwart, Hans Bieräugel, Bas de Bruin, Joost N. H. Reek, Jan H. van Maarseveen
Organic & Biomolecular Chemistry, 2022, 20(3), 575-578
DOI: 10.1039/d1ob02309h


      Phenol ester activated dipeptides that are reluctant to ring-close have been cyclised with the aid of sterically shielding metallo-porphyrins avoiding unwanted intermolecular reactions. The binding of ZnTPP to the dipyridine-functionalised activating phenolic ester was studied by NMR titrations and modelling. Staudinger-mediated cyclisations in the presence of ZnTPP increased the yield of the cyclic dipeptide from 16% to 40%.