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5-Hydroxy-pyrrolone based building blocks as maleimide alternatives for protein bioconjugation and single-site multi-functionalization.
De Geyter, Ewout; Antonatou, Eirini; Kalaitzakis, Dimitris; Smolen, Sabina; Iyer, Abhishek; Tack, Laure; Ongenae, Emiel; Vassilikogiannakis, Georgios; Madder, Annemieke.
Afiliação
  • De Geyter E; Organic and Biomimetic Chemistry Research Group OBCR, Department of Organic and Macromolecular Chemistry, Faculty of Sciences, Ghent University Krijgslaan 281 S4 9000 Ghent Belgium annemieke.madder@ugent.be.
  • Antonatou E; Organic and Biomimetic Chemistry Research Group OBCR, Department of Organic and Macromolecular Chemistry, Faculty of Sciences, Ghent University Krijgslaan 281 S4 9000 Ghent Belgium annemieke.madder@ugent.be.
  • Kalaitzakis D; Department of Chemistry, University of Crete Vasilika Vouton 71003 Iraklion Crete Greece vasil@uoc.gr.
  • Smolen S; Organic and Biomimetic Chemistry Research Group OBCR, Department of Organic and Macromolecular Chemistry, Faculty of Sciences, Ghent University Krijgslaan 281 S4 9000 Ghent Belgium annemieke.madder@ugent.be.
  • Iyer A; Organic and Biomimetic Chemistry Research Group OBCR, Department of Organic and Macromolecular Chemistry, Faculty of Sciences, Ghent University Krijgslaan 281 S4 9000 Ghent Belgium annemieke.madder@ugent.be.
  • Tack L; Organic and Biomimetic Chemistry Research Group OBCR, Department of Organic and Macromolecular Chemistry, Faculty of Sciences, Ghent University Krijgslaan 281 S4 9000 Ghent Belgium annemieke.madder@ugent.be.
  • Ongenae E; Organic and Biomimetic Chemistry Research Group OBCR, Department of Organic and Macromolecular Chemistry, Faculty of Sciences, Ghent University Krijgslaan 281 S4 9000 Ghent Belgium annemieke.madder@ugent.be.
  • Vassilikogiannakis G; Department of Chemistry, University of Crete Vasilika Vouton 71003 Iraklion Crete Greece vasil@uoc.gr.
  • Madder A; Organic and Biomimetic Chemistry Research Group OBCR, Department of Organic and Macromolecular Chemistry, Faculty of Sciences, Ghent University Krijgslaan 281 S4 9000 Ghent Belgium annemieke.madder@ugent.be.
Chem Sci ; 12(14): 5246-5252, 2021 Mar 04.
Article em En | MEDLINE | ID: mdl-34163760
ABSTRACT
Recent dramatic expansion in potential uses of protein conjugates has fueled the development of a wide range of protein modification methods; however, the desirable single-site multi-functionalization of proteins has remained a particularly intransigent challenge. Herein, we present the application of 5-hydroxy-1,5-dihydro-2H-pyrrol-2-ones (5HP2Os) as advantageous alternatives to widely used maleimides for the chemo- and site-selective labeling of cysteine residues within proteins. A variety of 5HP2O building blocks have been synthesized using a one-pot photooxidation reaction starting from simple and readily accessible furans and using visible light and oxygen. These novel reagents display excellent cysteine selectivity and also yield thiol conjugates with superior stability. 5HP2O building blocks offer a unique opportunity to introduce multiple new functionalities into a protein at a single site and in a single step, thus, significantly enhancing the resultant conjugate's properties.

Texto completo: 1 Base de dados: MEDLINE Idioma: En Revista: Chem Sci Ano de publicação: 2021 Tipo de documento: Article

Texto completo: 1 Base de dados: MEDLINE Idioma: En Revista: Chem Sci Ano de publicação: 2021 Tipo de documento: Article