Abstract
Cyclic peptides have wide utility in the biological sciences. As conformationally locked analogs of the parent linear peptides, they possess greater stability under physiological conditions and increased binding affinity for their targets. As investigations of biological processes often require reporter molecules and functional readouts, chemical probes are commonly appended with functional groups that allow for conjugation to biological entities. Herein we describe the functionalization of cyclic peptides prepared via aziridine aldehyde-mediated macrocyclization. These cyclic peptides contain an aziridine ring that can be further functionalized by ring opening with nucleophiles. We report on the methodology used to produce a cyclic peptide analog of Pro-Gly-Leu-Gly-Phe with either azido or sulfhydryl functionality.
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Acknowledgements
We thank the Natural Sciences and Engineering Research Council of Canada, Québec Consortium for Drug Discovery, Ontario Genomics Institute, and Ontario Graduate Scholarship Program (S.Z.) for financial support.
The authors wish to acknowledge the Canadian Foundation for Innovation, project number 19119, and the Ontario Research Fund for funding of the Centre for Spectroscopic Investigation of Complex Organic Molecules and Polymers.
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Zaretsky, S., Tan, J., Hickey, J.L., Yudin, A.K. (2015). Macrocyclic Templates for Library Synthesis of Peptido-Conjugates. In: Derda, R. (eds) Peptide Libraries. Methods in Molecular Biology, vol 1248. Humana Press, New York, NY. https://doi.org/10.1007/978-1-4939-2020-4_5
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DOI: https://doi.org/10.1007/978-1-4939-2020-4_5
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Print ISBN: 978-1-4939-2019-8
Online ISBN: 978-1-4939-2020-4
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