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

DOI: 10.1039/C7PY01953J DOI Help

Authors: Manuel Hartweg (Queen Mary University) , Charlotte J. C. Edwards-gayle (University of Reading; Diamond Light Source) , Elham Radvar (Queen Mary University) , Dominic W. P. Collis (Queen Mary University) , Mehedi Reza (Aalto University) , Michael Kaupp (Karlsruhe Institute of Technology (KIT)) , Jan Steink├Ânig (Karlsruhe Institute of Technology (KIT)) , Janne Ruokolainen (Aalto University) , Robert Rambo (Diamond Light Source) , Christopher Barner-kowollik (Karlsruhe Institute of Technology (KIT)) , Ian W. Hamley (Diamond Light Source) , Helena S. Azevedo (Queen Mary University) , C. Remzi Becer (Queen Mary University)
Co-authored by industrial partner: No

Type: Journal Paper
Journal: Polymer Chemistry

State: Published (Approved)
Published: December 2017
Diamond Proposal Number(s): 15778

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.

Subject Areas: Chemistry


Instruments: B21-High Throughput SAXS