Articles producció científica> Química Analítica i Química Orgànica

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

  • Identification data

    Identifier: imarina:9332594
    Handle: https://hdl.handle.net/20.500.11797/imarina9332594
    Authors:
    Bernús, MMazzarella, DStanic, JZhai, ZRYeste-Vázquez, ABoutureira, OGargano, AFGGrossmann, TNNoël, T
    Abstract:
    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.].

  • Others:

    Author, as appears in the article.: Bernús, M; Mazzarella, D; Stanic, J; Zhai, ZR; Yeste-Vázquez, A; Boutureira, O; Gargano, AFG; Grossmann, TN; Noël, T
    Department: Química Analítica i Química Orgànica
    URV's Author/s: Boutureira Martín, Omar
    Keywords: Sufex click chemistry
    Abstract: 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.].
    licence for use: https://creativecommons.org/licenses/by/3.0/es/
    Author's mail: omar.boutureira@urv.cat
    Author identifier: 0000-0002-0768-8309
    Record's date: 2024-01-17
    Papper version: info:eu-repo/semantics/acceptedVersion
    Papper original source: Nature Synthesis.
    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
    Licence document URL: https://repositori.urv.cat/ca/proteccio-de-dades/
    Entity: Universitat Rovira i Virgili
    Journal publication year: 2023
    Publication Type: Journal Publications