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Site-Specific Glycoconjugation of Protein via Bioorthogonal Tetrazine Cycloaddition with a Genetically Encoded trans-Cyclooctene or Bicyclononyne

Authors
Lang, Kathrin
Xue, Lin
Chin, Jason W.
Published in Bioconjugate Chemistry. 2015, vol. 26, no. 5, p. 802-806
Abstract 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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MACHIDA, Takuya et al. Site-Specific Glycoconjugation of Protein via Bioorthogonal Tetrazine Cycloaddition with a Genetically Encoded trans-Cyclooctene or Bicyclononyne. In: Bioconjugate Chemistry, 2015, vol. 26, n° 5, p. 802-806. https://archive-ouverte.unige.ch/unige:72784

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Deposited on : 2015-05-26

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