Inducible, site-specific protein labeling by tyrosine oxidation–strain-promoted (4+ 2) cycloaddition
JJ Bruins, AH Westphal, B Albada, K Wagner… - Bioconjugate …, 2017 - ACS Publications
Bioconjugate chemistry, 2017•ACS Publications
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.
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.
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.
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