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Spontaneous Aminolytic Cyclization and Self-Assembly of Dipeptide Methyl Esters in Water

preprint
submitted on 17.01.2020 and posted on 24.01.2020 by Charalampos Pappas, Nadeesha Wijerathne, Jugal Kishore Sahoo, Ankit Jain, Daniela Kroiss, Ivan R. Sasselli, Ana Pina, Ayala Lampel, Rein V. Ulijn
Dipeptides are known to spontaneously cyclize to diketopiperazines, and in some cases these cyclic dipeptides have been shown to self-assemble to form supramolecular nanostructures. Herein, we demonstrate the in situ cyclization of dipeptide methyl esters in aqueous buffer by intramolecular aminolysis, leading to the formation of diverse supramolecular nanostructures. The chemical nature of the amino acid side chains dictates the supramolecular arrangement and resulting nanoscale architectures. For c[LF], supramolecular gels are formed, and the concentration of starting materials influences the mechanical properties of hydrogels. Moreover, by adding metalloporphyrin to the starting dipeptide ester solution, these become incorporated through cooperative assembly, resulting in the formation of nanofibers able to catalyse the oxidation of organic phenol in water. The approach taken here, which combines the chemically activated assembly with the versatility of short peptides might pave the way for achieving the spontaneous formation of supramolecular order and function using simple building blocks.

History

Email Address of Submitting Author

c.pappas@rug.nl

Institution

University of Groningen

Country

The Netherlands

ORCID For Submitting Author

0000-0003-3019-9607

Declaration of Conflict of Interest

The authors declare no competing financial interests

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