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Issue 4, 2018

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

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Abstract

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.

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

Supplementary files

Article information


Submitted
21 Nov 2017
Accepted
20 Dec 2017
First published
21 Dec 2017

This article is Open Access

Polym. Chem., 2018,9, 482-489
Article type
Paper

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

M. Hartweg, C. J. C. Edwards-Gayle, E. Radvar, D. Collis, M. Reza, M. Kaupp, J. Steinkoenig, J. Ruokolainen, R. Rambo, C. Barner-Kowollik, I. W. Hamley, H. S. Azevedo and C. R. Becer, Polym. Chem., 2018, 9, 482 DOI: 10.1039/C7PY01953J

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

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