Papain-catalysed mechanochemical synthesis of oligopeptides by milling and twin-screw extrusion: application in the Julia-Colonna enantioselective epoxidation

Karen J. Ardila-Fierro, Deborah E. Crawford, Andrea Körner, Stuart L. James, Carsten Bolm, José G. Hernández

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34 Citations (Scopus)

Abstract

The oligomerisation of L-amino acids by papain was studied in a mixer ball mill and in a planetary ball mill. The biocatalyst proved stable under the ball milling conditions providing the corresponding oligopeptides in good to excellent yields and with a variable degree of polymerisation. Both parameters were found to be dependent on the reaction conditions and on the nature of the amino acid (specifically on its side-chain size and hydrophobicity). In addition, the chemoenzymatic oligomerisation was demonstrated by utilising twin-screw extrusion technology, which allowed for a scalable continuous process. Finally, the synthesised oligo(L-Leu) 2b proved to be active as a catalyst in the Juliá–Colonna enantioselective epoxidation of chalcone derivatives.
Original languageEnglish
Pages (from-to)1262-1269
JournalGreen Chemistry
Volume20
Issue number6
Early online date09 Jan 2018
DOIs
Publication statusPublished - 21 Mar 2018

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