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

Research output: Contribution to journalArticleScientificpeer-review

Researchers

  • 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

Research units

  • Queen Mary University of London
  • University of Reading
  • Diamond Light Source Ltd
  • Karlsruhe Institute of Technology
  • Queensland University of Technology

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.

Details

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

ID: 17485470