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

被引：89

作者：

Ardila-Fierro, Karen J. ^{[1
]}

Crawford, Deborah E. ^{[2
]}

Koerner, Andrea ^{[3
]}

James, Stuart L. ^{[2
]}

Bolm, Carsten ^{[1
]}

Hernandez, Jose G. ^{[1
]}

机构：

[1] Rhein Westfal TH Aachen, Inst Organ Chem, Landoltweg 1, D-52074 Aachen, Germany

[2] Queens Univ Belfast, Sch Chem & Chem Engn, David Keir Bldg,Stranmillis Rd, Belfast BT9 5AG, Antrim, North Ireland

[3] DWI Leibniz Inst Interact Mat eV, Forckenbeckstr 50, D-52074 Aachen, Germany

来源：

GREEN CHEMISTRY | 2018年 / 20卷 / 06期

基金：

英国工程与自然科学研究理事会;

关键词：

ACID-N-CARBOXYANHYDRIDES; PEPTIDE-SYNTHESIS; CHEMICAL-SYNTHESIS; ORGANIC-REACTIONS; AMINO-ACIDS; BALL MILLS; SCALE; SOLVENTS; POLYMERIZATION; PROTEINS;

D O I：

10.1039/c7gc03205f

中图分类号：

O6 [化学];

学科分类号：

070301 [无机化学];

摘要：

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 Julia-Colonna enantioselective epoxidation of chalcone derivatives.

引用

页码：1262 / 1269

页数：8

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