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

doi:10.1021/acs.bioconjchem.7b00046

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

Research output: Contribution to journal › Article › Academic › peer-review

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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 language	English
Pages (from-to)	1189-1193
Journal	Bioconjugate chemistry
Volume	28
Issue number	4
Early online date	2017
DOIs	https://doi.org/10.1021/acs.bioconjchem.7b00046
Publication status	Published - 2017

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Inducible-site-specific-protein-labeling-by-tyrosine-oxidation-strain-promoted-42-cycloaddition.pdfFinal published version, 1.59 MBLicence: Taverne

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

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",

author = "Bruins, \{Jorick J.\} and Westphal, \{Adrie H.\} and Bauke Albada and Koen Wagner and Lina Bartels and Hergen Spits and \{van Berkel\}, \{Willem J. H.\} and \{van Delft\}, \{Floris L.\}",

year = "2017",

doi = "10.1021/acs.bioconjchem.7b00046",

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T1 - Inducible, Site-Specific Protein Labeling by Tyrosine Oxidation-Strain-Promoted (4+2) Cycloaddition

AU - Bruins, Jorick J.

AU - Westphal, Adrie H.

AU - Albada, Bauke

AU - Wagner, Koen

AU - Bartels, Lina

AU - Spits, Hergen

AU - van Berkel, Willem J. H.

AU - van Delft, Floris L.

PY - 2017

Y1 - 2017

N2 - 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

AB - 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

U2 - 10.1021/acs.bioconjchem.7b00046

DO - 10.1021/acs.bioconjchem.7b00046

M3 - Article

C2 - 28263569

SN - 1043-1802

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SP - 1189

EP - 1193

JO - Bioconjugate chemistry

JF - Bioconjugate chemistry

IS - 4

ER -

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

Abstract

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