Ugi multicomponent reaction to prepare peptide–peptoid hybrid structures with diverse chemical functionalities

Hartweg, M., Edwards-Gayle, C. J. C., Radvar, E., Collis, D., Reza, M., Kaupp, M., Steinkoenig, J., Ruokolainen, J., Rambo, R., Barner-Kowollik, C., Hamley, I. W. ORCID: https://orcid.org/0000-0002-4549-0926, Azevedo, H. S. and Becer, C. R. (2018) Ugi multicomponent reaction to prepare peptide–peptoid hybrid structures with diverse chemical functionalities. Polymer Chemistry, 9 (4). pp. 482-489. ISSN 1759-9954 doi: 10.1039/c7py01953j

Abstract/Summary

Monodisperse sequenced peptides and peptoids present unique nano-structures based on their self-assembled secondary and tertiary structures. However, the generation of peptide and peptoid hybrid oligomers in a sequence-defined manner via Ugi multicomponent reaction has not yet been studied. Herein, we report a synthetic strategy that enables both the modification of peptides as well as the generation of sequence-defined peptide–peptoid hybrid structures. Our synthetic methodology rests on the fusion of solid phase peptide synthesis with Ugi multicomponent reactions. We evidence that a diversity of chemical functionalities can be inserted into peptides or used in the design of peptide–peptoid hybrids exploiting a wide functional array including amines, carboxylic acids, hydrocarbons, carbohydrates as well as polymers, introducing a sequence-defined synthetic platform technology for precision peptoid hybrids.

Item Type	Article
URI	https://reading-clone.eprints-hosting.org/id/eprint/75166
Identification Number/DOI	10.1039/c7py01953j
Refereed	Yes
Divisions	Life Sciences > School of Chemistry, Food and Pharmacy > Department of Chemistry
Uncontrolled Keywords	Organic Chemistry, Biochemistry, Bioengineering, Polymers and Plastics
Publisher	Royal Society of Chemistry
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