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公開
学術論文

Chemoselective umpolung of thiols to episulfoniums for cysteine bioconjugation

MPS-Authors
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Hartmann,  Philipp
Research Department Ritter, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Bohdan,  Kostiantyn
Research Department Ritter, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Hommrich,  Moritz
Research Department Ritter, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Juliá,  Fabio
Research Department Ritter, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Farès,  Christophe
Service Department Farès (NMR), Max-Planck-Institut für Kohlenforschung, Max Planck Society;

Jacobs,  Julia Beatrice
Research Department Ritter, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Mengeler,  Johanna Marie
Research Department Ritter, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Vetere,  Alessandro
Service Department Schrader (MS), Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Sterling,  Marie Sophie
Service Department Schulze (GC, HPLC), Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Hinrichs,  Heike
Service Department Schulze (GC, HPLC), Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Schrader,  Wolfgang
Service Department Schrader (MS), Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Ritter,  Tobias
Research Department Ritter, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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引用

Hartmann, P., Bohdan, K., Hommrich, M., Juliá, F., Vogelsang, L., Eirich, J., Zangl, R., Farès, C., Jacobs, J. B., Mukhopadhyay, D., Mengeler, J. M., Vetere, A., Sterling, M. S., Hinrichs, H., Becker, S., Morgner, N., Schrader, W., Finkemeier, I., Dietz, K.-J., Griesinger, C., & Ritter, T. (2024). Chemoselective umpolung of thiols to episulfoniums for cysteine bioconjugation. Nature Chemistry, 16, 380-388. doi:10.1038/s41557-023-01388-7.


引用: https://hdl.handle.net/21.11116/0000-000E-312E-8
要旨
Cysteine conjugation is an important tool in protein research and relies on fast, mild and chemoselective reactions. Cysteinyl thiols can either be modified with prefunctionalized electrophiles, or converted into electrophiles themselves for functionalization with selected nucleophiles in an independent step. Here we report a bioconjugation strategy that uses a vinyl thianthrenium salt to transform cysteine into a highly reactive electrophilic episulfonium intermediate in situ, to enable conjugation with a diverse set of bioorthogonal nucleophiles in a single step. The reactivity profile can connect several nucleophiles to biomolecules through a short and stable ethylene linker, ideal for introduction of infrared labels, post-translational modifications or NMR probes. In the absence of reactive exogenous nucleophiles, nucleophilic amino acids can react with the episulfonium intermediate for native peptide stapling and protein–protein ligation. Ready synthetic access to isotopologues of vinyl thianthrenium salts enables applications in quantitative proteomics. Such diverse applications demonstrate the utility of vinyl-thianthrenium-based bioconjugation as a fast, selective and broadly applicable tool for chemical biology.