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

Manuel Hartweg, Charlotte J.C. Edwards-Gayle, Elham Radvar, Dominic Collis, Mehedi Reza, Michael Kaupp, Jan Steinkoenig, Janne Ruokolainen, Robert Rambo, Christopher Barner-Kowollik, Ian W. Hamley, Helena S. Azevedo, C. Remzi Becer*

*Corresponding author for this work

Research output: Contribution to journalArticleScientificpeer-review

18 Citations (Scopus)
12 Downloads (Pure)

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.

Original languageEnglish
Pages (from-to)482-489
Number of pages8
JournalPolymer Chemistry
Volume9
Issue number4
DOIs
Publication statusPublished - 28 Jan 2018
MoE publication typeA1 Journal article-refereed

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