Papain-catalysed mechanochemical synthesis of oligopeptides by milling and twin-screw extrusion: application in the Juliá-Colonna enantioselective epoxidation
Ardila-Fierro, K. Crawford, Deborah E. Körner, A. James, S.L. Bolm, C. Hernández, J.G.
Ardila-Fierro, K.
Crawford, Deborah E.
Körner, A.
James, S.L.
Bolm, C.
Hernández, J.G.
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2018-01
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2018-01-09
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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.
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Ardila-Fierro KJ, Crawford DE, Körner A et al (2018) Papain-catalysed mechanochemical synthesis of ogliopeptides by milling and twin-screw extrusion: application in the Juliá–Colonna enantioselective epoxidation. Green Chemistry. 20(6): 1262-1269.
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