Journal
BIOCONJUGATE CHEMISTRY
Volume 26, Issue 5, Pages 802-806Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.bioconjchem.5b00101
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Funding
- Swiss National Science Foundation
- NCCR Chemical Biology
- MRC [MC_U105181009, MC_UP_A024_1008] Funding Source: UKRI
- Medical Research Council [MC_UP_A024_1008, MC_U105181009] Funding Source: researchfish
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Efficient access to proteins modified site-specifically with glycans is important in glycobiology and for therapeutic applications. Herein, we report a biocompatible protein glycoconjugation by inverse demand Diels-Alder reaction between tetrazine and trans-cyclooctene. Tetrazine functionalized glycans were obtained in one step by CuAAC (Cu-catalyzed alkyne azide cycloaddition) between glycosyl azide and an alkyne-tetrazine adduct. Site-specific glycoconjugation was performed chemoselectively on a target protein in which a trans-cyclooctene derivatized lysine was genetically encoded. Glycoconjugation proceeded to completion on purified protein and was shown to be selective for the target protein in E. coli.
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