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

[Image: see text] 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) deri...

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Autores principales: Bruins, Jorick J., Westphal, Adrie H., Albada, Bauke, Wagner, Koen, Bartels, Lina, Spits, Hergen, van Berkel, Willem J. H., van Delft, Floris L.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2017
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5399473/
https://www.ncbi.nlm.nih.gov/pubmed/28263569
http://dx.doi.org/10.1021/acs.bioconjchem.7b00046
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author Bruins, Jorick J.
Westphal, Adrie H.
Albada, Bauke
Wagner, Koen
Bartels, Lina
Spits, Hergen
van Berkel, Willem J. H.
van Delft, Floris L.
author_facet Bruins, Jorick J.
Westphal, Adrie H.
Albada, Bauke
Wagner, Koen
Bartels, Lina
Spits, Hergen
van Berkel, Willem J. H.
van Delft, Floris L.
author_sort Bruins, Jorick J.
collection PubMed
description [Image: see text] 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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spelling pubmed-53994732017-04-23 Inducible, Site-Specific Protein Labeling by Tyrosine Oxidation–Strain-Promoted (4 + 2) Cycloaddition Bruins, Jorick J. Westphal, Adrie H. Albada, Bauke Wagner, Koen Bartels, Lina Spits, Hergen van Berkel, Willem J. H. van Delft, Floris L. Bioconjug Chem [Image: see text] 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. American Chemical Society 2017-03-06 2017-04-19 /pmc/articles/PMC5399473/ /pubmed/28263569 http://dx.doi.org/10.1021/acs.bioconjchem.7b00046 Text en Copyright © 2017 American Chemical Society This is an open access article published under a Creative Commons Non-Commercial No Derivative Works (CC-BY-NC-ND) Attribution License (http://pubs.acs.org/page/policy/authorchoice_ccbyncnd_termsofuse.html) , which permits copying and redistribution of the article, and creation of adaptations, all for non-commercial purposes.
spellingShingle Bruins, Jorick J.
Westphal, Adrie H.
Albada, Bauke
Wagner, Koen
Bartels, Lina
Spits, Hergen
van Berkel, Willem J. H.
van Delft, Floris L.
Inducible, Site-Specific Protein Labeling by Tyrosine Oxidation–Strain-Promoted (4 + 2) Cycloaddition
title Inducible, Site-Specific Protein Labeling by Tyrosine Oxidation–Strain-Promoted (4 + 2) Cycloaddition
title_full Inducible, Site-Specific Protein Labeling by Tyrosine Oxidation–Strain-Promoted (4 + 2) Cycloaddition
title_fullStr Inducible, Site-Specific Protein Labeling by Tyrosine Oxidation–Strain-Promoted (4 + 2) Cycloaddition
title_full_unstemmed Inducible, Site-Specific Protein Labeling by Tyrosine Oxidation–Strain-Promoted (4 + 2) Cycloaddition
title_short Inducible, Site-Specific Protein Labeling by Tyrosine Oxidation–Strain-Promoted (4 + 2) Cycloaddition
title_sort inducible, site-specific protein labeling by tyrosine oxidation–strain-promoted (4 + 2) cycloaddition
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5399473/
https://www.ncbi.nlm.nih.gov/pubmed/28263569
http://dx.doi.org/10.1021/acs.bioconjchem.7b00046
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