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Orthogonal, dual protein labelling by tandem cycloaddition of strained alkenes and alkynes to ortho-quinones and azides

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Abstract

Reaction of cyclopropanated trans-cyclooctene (cpTCO) with in situ generated ortho-quinone is an efficient tool for bioorthogonal protein conjugation. The (4+2)-cycloaddition of cpTCO with ortho-quinone is significantly faster than its cyclooctyne counterpart (BCN). Orthogonal, tandem cpTCO–quinone and BCN–azide cycloadditions afforded a homogeneous, dual labelled antibody–drug conjugate.

Graphical abstract: Orthogonal, dual protein labelling by tandem cycloaddition of strained alkenes and alkynes to ortho-quinones and azides

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Publication details

The article was received on 02 Apr 2018, accepted on 06 Jun 2018 and first published on 07 Jun 2018


Article type: Communication
DOI: 10.1039/C8CC02638F
Citation: Chem. Commun., 2018, Advance Article
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    Orthogonal, dual protein labelling by tandem cycloaddition of strained alkenes and alkynes to ortho-quinones and azides

    J. J. Bruins, D. Blanco-Ania, V. van der Doef, F. L. van Delft and B. Albada, Chem. Commun., 2018, Advance Article , DOI: 10.1039/C8CC02638F

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