Redox-based reagents for chemoselective methionine bioconjugation

Lin, Shixian; Yang, Xiaoyu; Jia, Shang; Weeks, Amy M.; Hornsby, Michael; Lee, Peter S.; Nichiporuk, Rita V.; Iavarone, Anthony T.; Wells, James A.; Toste, F. Dean; Chang, Christopher J.

doi:10.1126/science.aal3316

Redox-based reagents for chemoselective methionine bioconjugation

Journal Article · Fri Feb 10 00:00:00 EST 2017 · Science

DOI:https://doi.org/10.1126/science.aal3316· OSTI ID:1465412

^[1]; ^[2]; ^[1]; ^[3]; ^[3]; ^[3]; ^[4]; Iavarone, Anthony T. ^[4]; ^[5]; ^[6]; ^[7]

Univ. of California, Berkeley, CA (United States). Dept. of Chemistry
Univ. of California, Berkeley, CA (United States). Dept. of Chemistry; ShanghaiTech Univ., Shanghai (China). School of Physical Science and Technology
Univ. of California, San Francisco, CA (United States). Dept. of Pharmaceutical Chemistry
Univ. of California, Berkeley, CA (United States). California Inst. for Quantitative Biosciences
Univ. of California, San Francisco, CA (United States). Dept. of Pharmaceutical Chemistry and Dept. of Cellular and Molecular Pharmacology
Univ. of California, Berkeley, CA (United States). Dept. of Chemistry; Lawrence Berkeley National Lab. (LBNL), Berkeley, CA (United States). Chemical Sciences Division
Univ. of California, Berkeley, CA (United States). Howard Hughes Medical Inst., Dept. of Chemistry and Dept. of Molecular and Cell Biology; Lawrence Berkeley National Lab. (LBNL), Berkeley, CA (United States). Chemical Sciences Division

Cysteine can be specifically functionalized by a myriad of acid-base conjugation strategies for applications ranging from probing protein function to antibody-drug conjugates and proteomics. In contrast, selective ligation to the other sulfur-containing amino acid, methionine, has been precluded by its intrinsically weaker nucleophilicity. In this work, we report a strategy for chemoselective methionine bioconjugation through redox reactivity, using oxaziridine-based reagents to achieve highly selective, rapid, and robust methionine labeling under a range of biocompatible reaction conditions. We highlight the broad utility of this conjugation method to enable precise addition of payloads to proteins, synthesis of antibody-drug conjugates, and identification of hyperreactive methionine residues in whole proteomes.

View Accepted Manuscript (DOE)

Research Organization:: Lawrence Berkeley National Laboratory (LBNL), Berkeley, CA (United States)

Sponsoring Organization:: National Inst. of Health (NIH); USDOE Office of Science (SC), Basic Energy Sciences (BES) (SC-22)

Grant/Contract Number:: AC02-05CH11231

OSTI ID:: 1465412

Journal Information:: Science, Journal Name: Science Journal Issue: 6325 Vol. 355; ISSN 0036-8075

Publisher:: AAASCopyright Statement

Country of Publication:: United States

Language:: English

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Structure-based design of targeted covalent inhibitors Lonsdale, Richard; Ward, Richard A. Chemical Society Reviews, Vol. 47, Issue 11 https://doi.org/10.1039/c7cs00220c	journal	January 2018
Arginine-selective bioconjugation with 4-azidophenyl glyoxal: application to the single and dual functionalisation of native antibodies Dovgan, Igor; Erb, Stéphane; Hessmann, Steve Organic & Biomolecular Chemistry, Vol. 16, Issue 8 https://doi.org/10.1039/c7ob02844j	journal	January 2018
A DNA-conjugated small molecule catalyst enzyme mimic for site-selective ester hydrolysis Flanagan, Moira L.; Arguello, A. Emilia; Colman, Drew E. Chemical Science, Vol. 9, Issue 8 https://doi.org/10.1039/c7sc04554a	journal	January 2018
Recent progress in enzymatic protein labelling techniques and their applications Zhang, Yi; Park, Keun-Young; Suazo, Kiall F. Chemical Society Reviews, Vol. 47, Issue 24 https://doi.org/10.1039/c8cs00537k	journal	January 2018
Chemical proteomic profiling of protein N -homocysteinylation with a thioester probe Chen, Nan; Liu, Jinmin; Qiao, Zeyu Chemical Science, Vol. 9, Issue 10 https://doi.org/10.1039/c8sc00221e	journal	January 2018
A sulfonium tethered peptide ligand rapidly and selectively modifies protein cysteine in vicinity Wang, Dongyuan; Yu, Mengying; Liu, Na Chemical Science, Vol. 10, Issue 19 https://doi.org/10.1039/c9sc00034h	journal	January 2019
A two-component protease in Methylorubrum extorquens with high activity toward the peptide precursor of the redox cofactor pyrroloquinoline quinone Martins, Ana M.; Latham, John A.; Martel, Paulo J. Journal of Biological Chemistry, Vol. 294, Issue 41 https://doi.org/10.1074/jbc.ra119.009684	journal	August 2019
Activity of the yeast cytoplasmic Hsp70 nucleotide-exchange factor Fes1 is regulated by reversible methionine oxidation Nicklow, Erin E.; Sevier, Carolyn S. Journal of Biological Chemistry, Vol. 295, Issue 2 https://doi.org/10.1074/jbc.ra119.010125	journal	December 2019
Contemporary approaches to site-selective protein modification Hoyt, Ea; Cal, Pmsd; Oliveira, Bl Apollo - University of Cambridge Repository https://doi.org/10.17863/cam.36322	text	January 2019
A protein functionalization platform based on selective reactions at methionine residues. Taylor, Michael T.; Nelson, Jennifer E.; Suero, Marcos G. Apollo - University of Cambridge Repository https://doi.org/10.17863/cam.37694	text	January 2018
Quaternization of Vinyl/Alkynyl Pyridine Enables Ultrafast Cysteine-Selective Protein Modification and Charge Modulation. Matos, Maria J.; Navo, Claudio D.; Hakala, Tuuli Apollo - University of Cambridge Repository https://doi.org/10.17863/cam.38446	text	January 2019

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