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Issue 4, 2018
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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

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Publication details

The article was received on 21 Nov 2017, accepted on 20 Dec 2017 and first published on 21 Dec 2017


Article type: Paper
DOI: 10.1039/C7PY01953J
Citation: Polym. Chem., 2018,9, 482-489
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    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

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