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Quantitative Heterodimerization of Aromatic Peptides through Host-Enhanced Polar–π Interactions for On-Resin Recognition

preprint
submitted on 04.05.2021, 22:47 and posted on 07.05.2021, 09:29 by Xiaoyi Chen, Zehuan Huang, Guanglu Wu, Kamil Sokłolowski, Katherine King, Jade McCune, Oren Scherman
Peptide dimerization plays an important role in both natural and artificial supramolecular systems. A major challenge to date is the quantitative heterodimerization of two peptides without formation of homodimers. Here, we employ a macrocyclic host to simultaneously encapsulate a canonical aromatic peptide and a non-canonical perfluorophenylalanine-containing peptide through polar–π interactions, thus forming an unprecedented new series of heteropeptide dimers with high binding affinity. This new peptide heterodimerization was applied to on-resin recognition and separation of aromatic peptides in a peptide mixture exhibiting over 95% isolation purity. This research unveils a generic approach to exploit quantitative heteropeptide dimers for the design of supramolecular (bio)systems.

Funding

NPIF EPSRC Doctoral - University of Cambridge 2017

Engineering and Physical Sciences Research Council

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Supramolecular Catalysis for Chemofixation and Electroreduction of CO2

European Commission

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ConfocAl Microscopy and real-time Rheology of dynamIc hyroGels

European Research Council

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Nano-Optics to controlled Nano-Chemistry Programme Grant (NOtCH)

Engineering and Physical Sciences Research Council

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History

Email Address of Submitting Author

oas23@cam.ac.uk

Institution

Yusuf Hamied Department of Chemistry, University of Cambridge

Country

United Kingdom

ORCID For Submitting Author

0000-0001-8032-7166

Declaration of Conflict of Interest

No conflict of interest

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