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

Jorick J. Bruins, Daniel Blanco-Ania, Vincent van der Doef, Floris L. van Delft*, Bauke Albada

*Corresponding author for this work

Research output: Contribution to journalArticleAcademicpeer-review

33 Citations (Scopus)

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.

Original languageEnglish
Pages (from-to)7338-7341
JournalChemical Communications
Volume54
Issue number53
DOIs
Publication statusPublished - 1 Jan 2018

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