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Cyclic assemblies 200120.pdf (2.78 MB)
Spontaneous Aminolytic Cyclization and Self-Assembly of Dipeptide Methyl Esters in Water
Preprints are manuscripts made publicly available before they have been submitted for formal peer review and publication. They might contain new research findings or data. Preprints can be a draft or final version of an author's research but must not have been accepted for publication at the time of submission.
submitted on 17.01.2020 and posted on 24.01.2020by 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.