Toward Light-Controlled Supramolecular Peptide Dimerization

Rita J Fernandes; Patricia Remón; Artur J Moro; André Seco; Ana S D Ferreira; Uwe Pischel; Nuno Basílio

doi:10.1021/acs.joc.1c00464

Toward Light-Controlled Supramolecular Peptide Dimerization

J Org Chem. 2021 Jun 18;86(12):8472-8478. doi: 10.1021/acs.joc.1c00464. Epub 2021 Jun 1.

Authors

Rita J Fernandes¹, Patricia Remón², Artur J Moro¹, André Seco¹, Ana S D Ferreira³, Uwe Pischel², Nuno Basílio¹

Affiliations

¹ Laboratorio Associado para a Química Verde (LAQV), Rede de Química e Tecnologia (REQUIMTE), Departamento de Química, Faculdade de Ciências e Tecnología, Universidade Nova de Lisboa, 2829-516 Caparica, Portugal.
² CIQSO - Centre for Research in Sustainable Chemistry and Department of Chemistry, University of Huelva, Campus de El Carmen s/n, E-21071 Huelva, Spain.
³ UCIBIO, REQUIMTE, Departamento de Química, Faculdade de Ciências e Tecnologia, Universidade Nova de Lisboa, 2829-516 Caparica, Portugal.

Abstract

The selective photodeprotection of the NVoc-modified FGG tripeptide yields the transformation of its 1:1 receptor-ligand complex with cucurbit[8]uril into a homoternary FGG₂@CB8 assembly. The resulting light-induced dimerization of the model peptide provides a tool for the implementation of stimuli-responsive supramolecular chemistry in biologically relevant contexts.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Bridged-Ring Compounds*
Dimerization
Imidazoles*
Peptides

Substances

Bridged-Ring Compounds
Imidazoles
Peptides