Issue 6, 2018

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

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.

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

Supplementary files

Article information

Article type
Paper
Submitted
24 okt 2017
Accepted
09 jan 2018
First published
09 jan 2018

Green Chem., 2018,20, 1262-1269

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

K. J. Ardila-Fierro, D. E. Crawford, A. Körner, S. L. James, C. Bolm and J. G. Hernández, Green Chem., 2018, 20, 1262 DOI: 10.1039/C7GC03205F

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