Accelerated Polypeptide Synthesis via N-Carboxyanhydride Ring Opening Polymerization in Continuous Flow

Jeroen Hendrik Vrijsen, Alicia Rasines Mazo, Tanja Junkers, Greg Guanghua Qiao

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1 Citation (Scopus)

Abstract

In nature, polypeptide-based materials are ubiquitous, yet their synthetic production is hampered by high cost, limited scalability, and often stringent reaction conditions. Herein an elegant approach is presented for N-carboxyanhydride ring opening polymerization (NCA ROP) of Nε-benzyloxycarbonyl-l-lysine (ZLL) and γ-benzyl-l-glutamate (BLG) NCA in continuous flow. The polymerization is initiated by primary amine initiators using N,N-dimethylformamide (DMF) as solvent. Carrying out the reaction in a silicon microflow reactor speeds up the rate of ROP (92% conversion in 40 min in flow as opposed to 6 h in batch) due to highly efficient permeation of CO2 through the reactor tubing. The polymerization strategy provides a facile, scale-up friendly alternative to traditional batch mode polymerization and has the capability of streamlining NCA ROP.

Original languageEnglish
Article number2000071
Number of pages6
JournalMacromolecular Rapid Communications
Volume41
Issue number18
DOIs
Publication statusPublished - 1 Sep 2020

Keywords

  • continuous flow chemistry
  • flow polymerization
  • N-carboxyanhydride ring opening polymerization

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