Controlled synthesis of β-sheet polymers based on side-chain amyloidogenic short peptide segmentsviaRAFT polymerization

Sonu Kumar,Priyadarsi De,Rituparna Acharya,Urmi Chatterji

doi:10.1039/c4py00620h

Abstract

A strategy was developed for the controlled synthesis of side-chain peptide containing pH-responsive polymers with an antiparallel β-sheet motif, which was independent of solvent polarity, PEGylation of homopolymers, the block length of PEG or peptidic segments in the block copolymer and temperature.

Highlights

In recent years, there has been growing interest in the development of synthetic strategies for the creation of multifunctional materials by taking inspiration from nature.[1,2,3] The palette of natural peptides or proteins offers an impressive scope for the design of novel structures and functionalities.[4]
Circular dichroism (CD) spectroscopy demonstrates the formation of a secondary structure from these peptidic polymers and they adopted the β-sheet conformation, which were stable against heat in the experimental temperature range and solvent polarity
Monomer synthesis The synthesis of the amyloidogenic short peptide derived monomer is summarized in Scheme S1.† Firstly, tripeptide Boc-LVF-OH was prepared by solution-phase synthesis (Fig. S1–S7†) and was coupled with hydroxyethyl methacrylate (HEMA) in the presence of DCC and DMAP to generate the side-chain peptide containing the methacrylate monomer, Boc-LVF-EMA

Summary

Introduction

There has been growing interest in the development of synthetic strategies for the creation of multifunctional materials by taking inspiration from nature.[1,2,3] The palette of natural peptides or proteins offers an impressive scope for the design of novel structures and functionalities.[4]. RAFT polymerization of the tripeptidic monomer Boc-LVF-EMA was carried out under similar conditions at 70 °C in DMF using AIBN as the initiator and CDP or mPEGn-CTA as RAFT agents for preparing peptidic sidechain homo- and block co-polymers.

Results

Conclusion