This chapter describes a reliable two-step, metal-free protocol for the preparation of well-defined fluoroglycoproteins. It starts with a first alkylation step to chemoselectively install strained alkyne handles at cysteine residues followed by a second strain-promoted azide–alkyne cycloaddition using an inverse electron-demand Diels–Alder reaction. This proof-of-principle study that uses the apoptotic protein marker Annexin V enables the efficient metal-free incorporation of 2-deoxy-2-fluoro-glycopyranosyl azides into proteins and complements previous methods using Cu(I)-mediated azide–alkyne cycloadditions and thiol chemistry.
This chapter describes a reliable two-step, metal-free protocol for the preparation of well-defined fluoroglycoproteins. It starts with a first alkylation step to chemoselectively install strained alkyne handles at cysteine residues followed by a second strain-promoted azide–alkyne cycloaddition using an inverse electron-demand Diels–Alder reaction. This proof-of-principle study that uses the apoptotic protein marker Annexin V enables the efficient metal-free incorporation of 2-deoxy-2-fluoro-glycopyranosyl azides into proteins and complements previous methods using Cu(I)-mediated azide–alkyne cycloadditions and thiol chemistry.
Title:
Fluoroglycoproteins by Copper-Free Strain-Promoted Azide–Alkyne Cycloaddition
Type:
Book Chapters
Contributor:
Universitat Rovira i Virgili Química Analítica i Química Orgànica
Peptide And Protein Engineering: From Concepts To Biotechnological …. 53-67
Repository ingest date:
2025-01-24
Referència ítem seogns Normas de la APA:
PMSD Cal; GJL Bernardes; O Boutureira (2020). Fluoroglycoproteins by Copper-Free Strain-Promoted Azide–Alkyne Cycloaddition. En . Peptide And Protein Engineering: From Concepts To Biotechnological … (pp. 53-67).