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Enzyme-Labile Protecting Groups for the Synthesis of Natural Products: Solid-Phase Synthesis of Thiocoraline

Authors

  • Dr. Judit Tulla-Puche,

    Corresponding author
    1. Institute for Research in Biomedicine Barcelona, CIBER-BBN, Baldiri Reixac 10, 08028 Barcelona (Spain)
    • Institute for Research in Biomedicine Barcelona, CIBER-BBN, Baldiri Reixac 10, 08028 Barcelona (Spain)

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  • Dr. Miriam Góngora-Benítez,

    1. Institute for Research in Biomedicine Barcelona, CIBER-BBN, Baldiri Reixac 10, 08028 Barcelona (Spain)
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  • Dr. Núria Bayó-Puxan,

    1. Institute for Research in Biomedicine Barcelona, CIBER-BBN, Baldiri Reixac 10, 08028 Barcelona (Spain)
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  • Dr. Andrés M. Francesch,

    1. PharmaMar S. A. Avda. de los Reyes 1, 28770 Colmenar Viejo, (Spain)
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  • Dr. Carmen Cuevas,

    1. PharmaMar S. A. Avda. de los Reyes 1, 28770 Colmenar Viejo, (Spain)
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  • Prof. Fernando Albericio

    Corresponding author
    1. Institute for Research in Biomedicine Barcelona, CIBER-BBN, Baldiri Reixac 10, 08028 Barcelona (Spain)
    2. Department of Organic Chemistry, University of Barcelona, Martí i Franquès 1, 08028 Barcelona (Spain)
    3. University of KwaZulu Natal, 4001-Durban (South Africa)
    • Institute for Research in Biomedicine Barcelona, CIBER-BBN, Baldiri Reixac 10, 08028 Barcelona (Spain)

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  • This study was funded by the CICYT (CTQ2012-30930), the Generalitat de Catalunya (2009SGR1024), and the Institute for Research in Biomedicine Barcelona (IRB Barcelona). We thank Dr. M. Gairí and Dr. M. Royo from the Barcelona Science Park for NMR technical support and for helpful discussions, respectively, and Dr. T. Bruckdorfer (Iris Biotech) for encouraging us to use Phacm.

Abstract

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Another (orthogonal) dimension: The solid-phase synthesis of thiocoraline was accomplished for the first time by a combined approach involving chemical and enzymatic methods. One-pot cleavage of the phenylacetamidomethyl protecting group using immobilized penicillin G acylase enzyme (see picture) and disulfide formation are the key steps of the synthetic strategy.

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