Site-selective photocatalytic functionalization of peptides and proteins at selenocysteine

Luke J. Dowman, Sameer S. Kulkarni, Juan V. Alegre-Requena, Andrew M. Giltrap, Alexander R. Norman, Ashish Sharma, Liliana C. Gallegos, Angus S. Mackay, Adarshi P. Welegedara, Emma E. Watson, Damian Raad, Gerhard Niederacher, Susanne Huhmann, Nicholas Proschogo, Karishma Patel, Mark Larance, Christian F. W. Becker, Joel P. Mackay, Girish Lakhwani, Thomas Huber, Robert S. Paton and Richard J. Payne ()
Additional contact information
Luke J. Dowman: The University of Sydney
Sameer S. Kulkarni: The University of Sydney
Juan V. Alegre-Requena: Colorado State University
Andrew M. Giltrap: The University of Sydney
Alexander R. Norman: The University of Sydney
Ashish Sharma: The University of Sydney
Liliana C. Gallegos: Colorado State University
Angus S. Mackay: The University of Sydney
Adarshi P. Welegedara: Australian National University
Emma E. Watson: The University of Sydney
Damian Raad: Australian National University
Gerhard Niederacher: University of Vienna
Susanne Huhmann: University of Vienna
Nicholas Proschogo: The University of Sydney
Karishma Patel: The University of Sydney
Mark Larance: The University of Sydney
Christian F. W. Becker: University of Vienna
Joel P. Mackay: The University of Sydney
Girish Lakhwani: The University of Sydney
Thomas Huber: Australian National University
Robert S. Paton: Colorado State University
Richard J. Payne: The University of Sydney

Nature Communications, 2022, vol. 13, issue 1, 1-12

Abstract: Abstract The importance of modified peptides and proteins for applications in drug discovery, and for illuminating biological processes at the molecular level, is fueling a demand for efficient methods that facilitate the precise modification of these biomolecules. Herein, we describe the development of a photocatalytic method for the rapid and efficient dimerization and site-specific functionalization of peptide and protein diselenides. This methodology, dubbed the photocatalytic diselenide contraction, involves irradiation at 450 nm in the presence of an iridium photocatalyst and a phosphine and results in rapid and clean conversion of diselenides to reductively stable selenoethers. A mechanism for this photocatalytic transformation is proposed, which is supported by photoluminescence spectroscopy and density functional theory calculations. The utility of the photocatalytic diselenide contraction transformation is highlighted through the dimerization of selenopeptides, and by the generation of two families of protein conjugates via the site-selective modification of calmodulin containing the 21st amino acid selenocysteine, and the C-terminal modification of a ubiquitin diselenide.

Date: 2022
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DOI: 10.1038/s41467-022-34530-z

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