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Labeling Proteins at Site-Specifically Incorporated 5-Hydroxytryptophan Residues Using a Chemoselective Rapid Azo-Coupling Reaction

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Bioconjugation

Part of the book series: Methods in Molecular Biology ((MIMB,volume 2033))

Abstract

Chemoselective protein labeling is a valuable tool in the arsenal of modern chemical biology. The unnatural amino acid mutagenesis technology provides a powerful way to site-specifically introduce nonnatural chemical functionalities into recombinant proteins, which can be subsequently functionalized in a chemoselective manner. Even though several strategies currently exist to selectively label recombinant proteins in this manner, there is considerable interest for the development of additional chemoselective reactions that are fast, catalyst-free, use readily available reagents, and are compatible with existing conjugation chemistries. Here we describe a method to express recombinant proteins in E. coli site-specifically incorporating 5-hydroxytryptophan, followed by the chemoselective labeling of this residue using a chemoselective rapid azo-coupling reaction.

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Acknowledgments

This work was supported by NIH (R01GM124319 to A.C.).

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Authors and Affiliations

  1. Department of Chemistry, Boston College, Chestnut Hill, MA, USA

    Partha Sarathi Addy, Sarah B. Erickson, James S. Italia & Abhishek Chatterjee

Authors
  1. Partha Sarathi Addy
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  2. Sarah B. Erickson
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  3. James S. Italia
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  4. Abhishek Chatterjee
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Corresponding author

Correspondence to Abhishek Chatterjee .

Editor information

Editors and Affiliations

  1. Cellular and Molecular Immunology Laboratory, Vrije Universiteit Brussel, Brussels, Belgium

    Sam Massa

  2. In Vivo Cellular and Molecular Imaging Laboratory (ICMI), Vrije Universiteit Brussel, Brussels, Belgium

    Nick Devoogdt

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Addy, P.S., Erickson, S.B., Italia, J.S., Chatterjee, A. (2019). Labeling Proteins at Site-Specifically Incorporated 5-Hydroxytryptophan Residues Using a Chemoselective Rapid Azo-Coupling Reaction. In: Massa, S., Devoogdt, N. (eds) Bioconjugation. Methods in Molecular Biology, vol 2033. Humana, New York, NY. https://doi.org/10.1007/978-1-4939-9654-4_16

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  • DOI: https://doi.org/10.1007/978-1-4939-9654-4_16

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  • Publisher Name: Humana, New York, NY

  • Print ISBN: 978-1-4939-9653-7

  • Online ISBN: 978-1-4939-9654-4

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