Late-stage peptide labeling with near-infrared fluorogenic nitrobenzodiazoles by manganese-catalyzed C–H activation
2023 | journal article. A publication with affiliation to the University of Göttingen.
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Late-stage peptide labeling with near-infrared fluorogenic nitrobenzodiazoles by manganese-catalyzed C–H activation
Oyama, T. ; Mendive-Tapia, L.; Cowell, V.; Kopp, A.; Vendrell, M. & Ackermann, L. (2023)
Chemical Science, 14(21) pp. 5728-5733. DOI: https://doi.org/10.1039/D3SC01868G
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Details
- Authors
- Oyama, Tsuyoshi ; Mendive-Tapia, Lorena; Cowell, Verity; Kopp, Adelina; Vendrell, Marc; Ackermann, Lutz
- Abstract
- This manganese-catalyzed late-stage NBD peptide labeling featured excellent site- and diastereo- E -selectivity, enabling large Stokes shifts, fluorogenic NIR emission, and application for real-time imaging of live bacteria under wash free conditions.
Late-stage diversification of structurally complex amino acids and peptides provides tremendous potential for drug discovery and molecular imaging. Specifically, labeling peptides with fluorescent tags is one of the most important methods for visualizing their mode of operation. Despite major recent advances in the field, direct molecular peptide labeling by C–H activation is largely limited to dyes with relatively short emission wavelengths, leading to high background signals and poor signal-to-noise ratios. In sharp contrast, here we report on the fluorescent labeling of peptides catalyzed by non-toxic manganese( i ) via C(sp 2 )–H alkenylation in chemo- and site-selective manners, providing modular access to novel near-infrared (NIR) nitrobenzodiazole-based peptide fluorogenic probes. - Issue Date
- 2023
- Journal
- Chemical Science
- Organization
- Institut für Organische und Biomolekulare Chemie
- ISSN
- 2041-6520
- eISSN
- 2041-6539
- Language
- English
- Sponsor
- Deutsche Forschungsgemeinschaft https://doi.org/10.13039/501100001659
H2020 European Research Council https://doi.org/10.13039/100010663
Horizon 2020 Framework Programme https://doi.org/10.13039/100010661
Wellcome Trust https://doi.org/10.13039/100010269
Deutsches Zentrum für Herz-Kreislaufforschung https://doi.org/10.13039/100010447
Leibniz-Gemeinschaft https://doi.org/10.13039/501100001664
University of Edinburgh https://doi.org/10.13039/501100000848