Inducible, Site-Specific Protein Labeling by Tyrosine Oxidation-Strain-Promoted (4 + 2) Cycloaddition

Jorick J. Bruins, Adrie H. Westphal, Bauke Albada, Koen Wagner, Lina Bartels, Hergen Spits, Willem J.H. van Berkel, Floris L. van Delft*

*Corresponding author for this work

Research output: Contribution to journalArticleAcademicpeer-review

43 Citations (Scopus)

Abstract

Genetically encoded tyrosine (Y-tag) can be utilized as a latent anchor for inducible and site-selective conjugation. Upon oxidation of tyrosine with mushroom tyrosinase, strain-promoted cycloaddition (SPOCQ) of the resulting 1,2-quinone with various bicyclo[6.1.0]nonyne (BCN) derivatives led to efficient conjugation. The method was applied for fluorophore labeling of laminarinase A and for the site-specific preparation of an antibody-drug conjugate.

Original languageEnglish
Pages (from-to)1189-1193
JournalBioconjugate Chemistry
Volume28
Issue number4
DOIs
Publication statusPublished - 2017

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