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COMU: scope and limitations of the latest innovation in peptide acyl transfer reagents

Authors

  • Ramon Subirós-Funosas,

    1. Chemistry and Molecular Pharmacology Program, Institute for Research in Biomedicine, Barcelona Science Park, Barcelona, Spain
    2. CIBER-BBN, Networking Centre on Bioengineering, Biomaterials and Nanomedicine, Barcelona Science Park, Barcelona, Spain
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  • Lidia Nieto-Rodriguez,

    1. Chemistry and Molecular Pharmacology Program, Institute for Research in Biomedicine, Barcelona Science Park, Barcelona, Spain
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  • Knud J. Jensen,

    Corresponding author
    • Department of Chemistry, Faculty of Science, University of Copenhagen, Frederiksberg, Denmark
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  • Fernando Albericio

    Corresponding author
    1. Chemistry and Molecular Pharmacology Program, Institute for Research in Biomedicine, Barcelona Science Park, Barcelona, Spain
    2. CIBER-BBN, Networking Centre on Bioengineering, Biomaterials and Nanomedicine, Barcelona Science Park, Barcelona, Spain
    3. Department of Organic Chemistry, University of Barcelona, Barcelona, Spain
    • School of Chemistry, University of KwaZulu-Natal4041, Durban, South Africa
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Correspondence to: Fernando Albericio, Chemistry and Molecular Pharmacology Program, Institute for Research in Biomedicine, Barcelona Science Park Baldiri Reixac 10, 08028 Barcelona, Spain. E-mail: albericio@irbbarcelona.org

K. J. Jensen, Department of Chemistry, Faculty of Science, University of Copenhagen, Thorvaldsensvej 40, 1871 Frederiksberg, Denmark. E-mail: kjj@chem.ku.dk

Abstract

The methodology for peptide bond formation is undergoing a continuous evolution where the main actors are being renewed. In recent years, coupling reagents based on the Oxyma scaffold, such as the uronium salt COMU, has been a groundbreaking contribution to the field. The advantages of COMU over classic benzotriazole-based reagents (HATU, HBTU, HCTU, TBTU) were proven in terms of solubility and coupling efficiency in bulky junctions in our groups and others. However, some aspects of the use of COMU need to be revised and improved, such as the stability of commercial samples in organic solvents, which hampers the compatibility with long synthesis in automated synthesizers. In this review, an overview of the main features and suggestions to improve the use of COMU are presented, along with a discussion on the best conditions for its use in microwave-assisted peptide robots. Copyright © 2013 European Peptide Society and John Wiley & Sons, Ltd.

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