A Chemoselective Rapid Azo-Coupling Reaction (CRACR) for Unclickable Bioconjugation

Chemoselective modification of complex biomolecules has become a cornerstone of chemical biology. Despite the exciting developments of the past two decades, the demand for new chemoselective reactions with unique abilities, and those compatible with existing chemistries for concurrent multisite-dire...

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Published in:	Journal of the American Chemical Society Vol. 139; no. 34; pp. 11670 - 11673
Main Authors:	Addy, Partha Sarathi, Erickson, Sarah B., Italia, James S., Chatterjee, Abhishek
Format:	Journal Article
Language:	English
Published:	WASHINGTON Amer Chemical Soc 30.08.2017
Subjects:	5-Hydroxytryptophan - chemistry Animals Azo Compounds - chemistry Bacterial Proteins - chemistry Cell Line Chemistry Chemistry, Multidisciplinary Click Chemistry - methods Escherichia coli - chemistry Fluorescent Dyes - chemistry Humans Immunoconjugates - chemistry Indoles - chemistry Models, Molecular Physical Sciences Proteins - chemistry Science & Technology Staining and Labeling - methods AZIDE-ALKYNE CYCLOADDITION BIOORTHOGONAL REACTIONS TOBACCO-MOSAIC-VIRUS GENETIC-CODE CLICK CHEMISTRY SURFACE MODIFICATION UNNATURAL AMINO-ACIDS MAMMALIAN-CELLS SELECTIVE MODIFICATION TRANS-CYCLOOCTENES
ISSN:	0002-7863, 1520-5126, 1520-5126
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Abstract	Chemoselective modification of complex biomolecules has become a cornerstone of chemical biology. Despite the exciting developments of the past two decades, the demand for new chemoselective reactions with unique abilities, and those compatible with existing chemistries for concurrent multisite-directed labeling, remains high. Here we show that 5-hydroxyindoles exhibit remarkably high reactivity toward aromatic diazonium ions and this reaction can be used to chemoselectively label proteins. We have previously genetically encoded the noncanonical amino acid 5-hydroxytryptophan in both E. coli and eitkaryotes, enabling efficient site-specific incorporation of S-hydroxyindole into virtually any protein. The S-hydroxytryptophan residue was shown to allow rapid; chemoselective protein modification using the azocoupling reaction, and the utility of this bioconjugation strategy was further illustrated by generating a functional antibody fluorophore conjugate. Although the resulting azo-linkage is otherwise stable, we show that it can be efficiently cleaved upon treatment with dithionite. Our work establishes a unique chemoselective "unclickable" bioconjugation strategy to site-specifically modify proteins expressed in both bacteria and eukaryotes.
AbstractList	Chemoselective modification of complex biomolecules has become a cornerstone of chemical biology. Despite the exciting developments of the past two decades, the demand for new chemoselective reactions with unique abilities, and those compatible with existing chemistries for concurrent multisite-directed labeling, remains high. Here we show that 5-hydroxyindoles exhibit remarkably high reactivity toward aromatic diazonium ions and this reaction can be used to chemoselectively label proteins. We have previously genetically encoded the noncanonical amino acid 5-hydroxytryptophan in both E. coli and eitkaryotes, enabling efficient site-specific incorporation of S-hydroxyindole into virtually any protein. The S-hydroxytryptophan residue was shown to allow rapid; chemoselective protein modification using the azocoupling reaction, and the utility of this bioconjugation strategy was further illustrated by generating a functional antibody fluorophore conjugate. Although the resulting azo-linkage is otherwise stable, we show that it can be efficiently cleaved upon treatment with dithionite. Our work establishes a unique chemoselective "unclickable" bioconjugation strategy to site-specifically modify proteins expressed in both bacteria and eukaryotes. Chemoselective modification of complex biomolecules has become a cornerstone of chemical biology. Despite the exciting developments of the past two decades, the demand for new chemoselective reactions with unique abilities, and those compatible with existing chemistries for concurrent multisite-directed labeling, remains high. Here we show that 5-hydroxyindoles exhibit remarkably high reactivity toward aromatic diazonium ions and this reaction can be used to chemoselectively label proteins. We have previously genetically encoded the noncanonical amino acid 5-hydroxytryptophan in both E. coli and eukaryotes, enabling efficient site-specific incorporation of 5-hydroxyindole into virtually any protein. The 5-hydroxytryptophan residue was shown to allow rapid, chemoselective protein modification using the azo-coupling reaction, and the utility of this bioconjugation strategy was further illustrated by generating a functional antibody-fluorophore conjugate. Although the resulting azo-linkage is otherwise stable, we show that it can be efficiently cleaved upon treatment with dithionite. Our work establishes a unique chemoselective "unclickable" bioconjugation strategy to site-specifically modify proteins expressed in both bacteria and eukaryotes.Chemoselective modification of complex biomolecules has become a cornerstone of chemical biology. Despite the exciting developments of the past two decades, the demand for new chemoselective reactions with unique abilities, and those compatible with existing chemistries for concurrent multisite-directed labeling, remains high. Here we show that 5-hydroxyindoles exhibit remarkably high reactivity toward aromatic diazonium ions and this reaction can be used to chemoselectively label proteins. We have previously genetically encoded the noncanonical amino acid 5-hydroxytryptophan in both E. coli and eukaryotes, enabling efficient site-specific incorporation of 5-hydroxyindole into virtually any protein. The 5-hydroxytryptophan residue was shown to allow rapid, chemoselective protein modification using the azo-coupling reaction, and the utility of this bioconjugation strategy was further illustrated by generating a functional antibody-fluorophore conjugate. Although the resulting azo-linkage is otherwise stable, we show that it can be efficiently cleaved upon treatment with dithionite. Our work establishes a unique chemoselective "unclickable" bioconjugation strategy to site-specifically modify proteins expressed in both bacteria and eukaryotes. Chemoselective modification of complex biomolecules has become a cornerstone of chemical biology. Despite the exciting developments of the past two decades, the demand for new chemoselective reactions with unique abilities, and those compatible with existing chemistries for concurrent multisite-directed labeling, remains high. Here we show that 5-hydroxyindoles exhibit remarkably high reactivity toward aromatic diazonium ions and this reaction can be used to chemoselectively label proteins. We have previously genetically encoded the noncanonical amino acid 5-hydroxytryptophan in both E. coli and eukaryotes, enabling efficient site-specific incorporation of 5-hydroxyindole into virtually any protein. The 5-hydroxytryptophan residue was shown to allow rapid, chemoselective protein modification using the azo-coupling reaction, and the utility of this bioconjugation strategy was further illustrated by generating a functional antibody-fluorophore conjugate. Although the resulting azo-linkage is otherwise stable, we show that it can be efficiently cleaved upon treatment with dithionite. Our work establishes a unique chemoselective "unclickable" bioconjugation strategy to site-specifically modify proteins expressed in both bacteria and eukaryotes.
Author	Chatterjee, Abhishek Erickson, Sarah B. Addy, Partha Sarathi Italia, James S.
Author_xml	– sequence: 1 givenname: Partha Sarathi orcidid: 0000-0002-0516-7307 surname: Addy fullname: Addy, Partha Sarathi organization: Boston Coll, Dept Chem, Merkert Chem Ctr 246B, 2609 Beacon St, Chestnut Hill, MA 02467 USA – sequence: 2 givenname: Sarah B. surname: Erickson fullname: Erickson, Sarah B. organization: Boston Coll, Dept Chem, Merkert Chem Ctr 246B, 2609 Beacon St, Chestnut Hill, MA 02467 USA – sequence: 3 givenname: James S. surname: Italia fullname: Italia, James S. organization: Boston Coll, Dept Chem, Merkert Chem Ctr 246B, 2609 Beacon St, Chestnut Hill, MA 02467 USA – sequence: 4 givenname: Abhishek orcidid: 0000-0002-6231-5302 surname: Chatterjee fullname: Chatterjee, Abhishek email: abhishek.chatterjee@bc.edu organization: Boston Coll, Dept Chem, Merkert Chem Ctr 246B, 2609 Beacon St, Chestnut Hill, MA 02467 USA
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Keywords	AZIDE-ALKYNE CYCLOADDITION BIOORTHOGONAL REACTIONS TOBACCO-MOSAIC-VIRUS GENETIC-CODE CLICK CHEMISTRY SURFACE MODIFICATION UNNATURAL AMINO-ACIDS MAMMALIAN-CELLS SELECTIVE MODIFICATION TRANS-CYCLOOCTENES
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Snippet	Chemoselective modification of complex biomolecules has become a cornerstone of chemical biology. Despite the exciting developments of the past two decades,...
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SubjectTerms	5-Hydroxytryptophan - chemistry Animals Azo Compounds - chemistry Bacterial Proteins - chemistry Cell Line Chemistry Chemistry, Multidisciplinary Click Chemistry - methods Escherichia coli - chemistry Fluorescent Dyes - chemistry Humans Immunoconjugates - chemistry Indoles - chemistry Models, Molecular Physical Sciences Proteins - chemistry Science & Technology Staining and Labeling - methods
Title	A Chemoselective Rapid Azo-Coupling Reaction (CRACR) for Unclickable Bioconjugation
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