Articles producció científica> Química Analítica i Química Orgànica

A modular flow platform for sulfur(VI) fluoride exchange ligation of small molecules, peptides and proteins

  • Datos identificativos

    Identificador: imarina:9332594
    Handle: https://hdl.handle.net/20.500.11797/imarina9332594
    Autores:
    Bernús, MMazzarella, DStanic, JZhai, ZRYeste-Vázquez, ABoutureira, OGargano, AFGGrossmann, TNNoël, T
    Resumen:
    Sulfur(VI) fluoride exchange click chemistry is a formidable tool to rapidly and effectively link chemical structures. Despite advances in the field in recent years, the installation of the sulfonyl fluoride handle still requires the use of purpose-designed, expensive and non-atom-economic reagents. The use of the SO2F2 for sulfonyl fluoride synthesis has been thwarted by the difficulties associated with the manipulation and dosage of this toxic gas, and by its apparent low reactivity with amino functionalities. Here we report a modular flow platform that can generate on demand, and efficiently dose, gaseous SO2F2. The use of flow technologies allows many lingering limitations of this transformation to be overcome, resulting in reduced reaction times, efficient reactivity and broad substrate scope. The effectiveness of the process was demonstrated by the successful synthesis of a diverse set of fluorosulfates and sulfamoyl fluorides, including those derived from biorelevant compounds, peptides and proteins. [Figure not available: see fulltext.].

  • Otros:

    Autor según el artículo: Bernús, M; Mazzarella, D; Stanic, J; Zhai, ZR; Yeste-Vázquez, A; Boutureira, O; Gargano, AFG; Grossmann, TN; Noël, T
    Departamento: Química Analítica i Química Orgànica
    Autor/es de la URV: Boutureira Martín, Omar
    Palabras clave: Sufex click chemistry
    Resumen: Sulfur(VI) fluoride exchange click chemistry is a formidable tool to rapidly and effectively link chemical structures. Despite advances in the field in recent years, the installation of the sulfonyl fluoride handle still requires the use of purpose-designed, expensive and non-atom-economic reagents. The use of the SO2F2 for sulfonyl fluoride synthesis has been thwarted by the difficulties associated with the manipulation and dosage of this toxic gas, and by its apparent low reactivity with amino functionalities. Here we report a modular flow platform that can generate on demand, and efficiently dose, gaseous SO2F2. The use of flow technologies allows many lingering limitations of this transformation to be overcome, resulting in reduced reaction times, efficient reactivity and broad substrate scope. The effectiveness of the process was demonstrated by the successful synthesis of a diverse set of fluorosulfates and sulfamoyl fluorides, including those derived from biorelevant compounds, peptides and proteins. [Figure not available: see fulltext.].
    Acceso a la licencia de uso: https://creativecommons.org/licenses/by/3.0/es/
    Direcció de correo del autor: omar.boutureira@urv.cat
    Identificador del autor: 0000-0002-0768-8309
    Fecha de alta del registro: 2024-01-17
    Versión del articulo depositado: info:eu-repo/semantics/acceptedVersion
    Referencia al articulo segun fuente origial: Nature Synthesis.
    Referencia de l'ítem segons les normes APA: Bernús, M; Mazzarella, D; Stanic, J; Zhai, ZR; Yeste-Vázquez, A; Boutureira, O; Gargano, AFG; Grossmann, TN; Noël, T (2023). A modular flow platform for sulfur(VI) fluoride exchange ligation of small molecules, peptides and proteins. Nature Synthesis, (), -. DOI: 10.1038/s44160-023-00441-0
    URL Documento de licencia: https://repositori.urv.cat/ca/proteccio-de-dades/
    Entidad: Universitat Rovira i Virgili
    Año de publicación de la revista: 2023
    Tipo de publicación: Journal Publications