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

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

doi:10.1039/c7py01953j

Abstract

Sequence defined peptide–peptoid hybrids create new opportunities for self-assembled nano-structures.

Highlights

Amongst a range of methods for the synthesis of such sequence-defined macromolecules, Merrifield solid phase peptide synthesis (SPPS) method has been the most successful.[4,5,6,7,8,9,10,11,12,13,14,15,16,17] Solid-phase protocols typically use excess of reagents and require two steps, which are the coupling and deprotection steps, for incorporation of each repeat unit
Our synthetic methodology rests on the fusion of solid phase peptide synthesis with Ugi multicomponent reactions
The preliminary considerations indicated that the distinct reaction protocols of conventional SPPS and Ugi-SPPS are suitable for iterative, random, or programmed sequence-defined solid phase synthesis

Summary

Introduction

Amongst a range of methods for the synthesis of such sequence-defined macromolecules, Merrifield solid phase peptide synthesis (SPPS) method has been the most successful.[4,5,6,7,8,9,10,11,12,13,14,15,16,17] Solid-phase protocols typically use excess of reagents and require two steps, which are the coupling and deprotection steps, for incorporation of each repeat unit. Ugi multicomponent reaction to prepare peptide– peptoid hybrid structures with diverse chemical functionalities† Cite this: Polym.

Results

Conclusion