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

Research output: Contribution to journalArticle

29 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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Papain
Oligopeptides
Oligomerization
Epoxidation
Ball mills
extrusion
Extrusion
Amino acids
mill
amino acid
Chalcone
Amino Acids
Biocatalysts
Ball milling
hydrophobicity
Hydrophobicity
polymerization
catalyst
Polymerization
Derivatives

Cite this

Ardila-Fierro, Karen J. ; Crawford, Deborah E. ; Körner, Andrea ; James, Stuart L. ; Bolm, Carsten ; Hernández, José G. . / Papain-catalysed mechanochemical synthesis of oligopeptides by milling and twin-screw extrusion: application in the Julia-Colonna enantioselective epoxidation. In: Green Chemistry. 2018 ; Vol. 20, No. 6. pp. 1262-1269 .
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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 Juli{\'a}–Colonna enantioselective epoxidation of chalcone derivatives.",
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Papain-catalysed mechanochemical synthesis of oligopeptides by milling and twin-screw extrusion: application in the Julia-Colonna enantioselective epoxidation. / Ardila-Fierro, Karen J.; Crawford, Deborah E.; Körner, Andrea ; James, Stuart L.; Bolm, Carsten; Hernández, José G. .

In: Green Chemistry, Vol. 20, No. 6, 21.03.2018, p. 1262-1269 .

Research output: Contribution to journalArticle

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AU - James, Stuart L.

AU - Bolm, Carsten

AU - Hernández, José G.

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AB - 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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