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Issue 5, 2013
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Environmentally benign peptide synthesis using liquid-assisted ball-milling: application to the synthesis of Leu-enkephalin

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Abstract

This paper describes an original methodology for peptide bond synthesis avoiding toxic solvents and reactants. Ball-milling stoichiometric amounts of Boc-protected α-amino acid N-carboxyanhydrides (Boc-AA-NCA) or Boc-protected α-amino acid N-hydroxysuccinimide esters (Boc-AA-OSu) with α-amino acid alkyl ester salts in the presence of NaHCO3 and a minimal quantity of EtOAc led to the production of di- to pentapeptides in an efficient and environmentally benign manner. This approach was successfully applied to the synthesis of Leu-enkephalin.

Graphical abstract: Environmentally benign peptide synthesis using liquid-assisted ball-milling: application to the synthesis of Leu-enkephalin

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Publication details

The article was received on 12 Feb 2013, accepted on 11 Mar 2013 and first published on 12 Mar 2013


Article type: Communication
DOI: 10.1039/C3GC40302E
Citation: Green Chem., 2013,15, 1116-1120
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    Environmentally benign peptide synthesis using liquid-assisted ball-milling: application to the synthesis of Leu-enkephalin

    J. Bonnamour, T. Métro, J. Martinez and F. Lamaty, Green Chem., 2013, 15, 1116
    DOI: 10.1039/C3GC40302E

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