Academic Journal
Cysteine-Targeting Gd-Based Spin Label and Its Application in Electron Paramagnetic Resonance Spectroscopy.
| Τίτλος: | Cysteine-Targeting Gd-Based Spin Label and Its Application in Electron Paramagnetic Resonance Spectroscopy. |
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| Συγγραφείς: | Yao X; Faculty of Chemistry and Center of Molecular Materials (CM2), Bielefeld University, Universitätsstraße 25, Bielefeld 33615, Germany., Landwehr E; Department of Chemistry and Konstanz Research School Chemical Biology, University of Konstanz, Universitätsstraße 10, Konstanz 78464, Germany., Qi M; Faculty of Chemistry and Center of Molecular Materials (CM2), Bielefeld University, Universitätsstraße 25, Bielefeld 33615, Germany., Hülsmann M; Faculty of Chemistry and Center of Molecular Materials (CM2), Bielefeld University, Universitätsstraße 25, Bielefeld 33615, Germany., Drescher M; Department of Chemistry and Konstanz Research School Chemical Biology, University of Konstanz, Universitätsstraße 10, Konstanz 78464, Germany., Godt A; Faculty of Chemistry and Center of Molecular Materials (CM2), Bielefeld University, Universitätsstraße 25, Bielefeld 33615, Germany. |
| Πηγή: | Bioconjugate chemistry [Bioconjug Chem] 2025 Oct 15; Vol. 36 (10), pp. 2267-2286. Date of Electronic Publication: 2025 Sep 25. |
| Τύπος έκδοσης: | Journal Article; Research Support, Non-U.S. Gov't |
| Γλώσσα: | English |
| Στοιχεία περιοδικού: | Publisher: American Chemical Society Country of Publication: United States NLM ID: 9010319 Publication Model: Print-Electronic Cited Medium: Internet ISSN: 1520-4812 (Electronic) Linking ISSN: 10431802 NLM ISO Abbreviation: Bioconjug Chem Subsets: MEDLINE |
| Imprint Name(s): | Original Publication: Washington, DC : American Chemical Society, c1990- |
| Ιατρικοί όροι (MeSH): | Cysteine*/chemistry , Gadolinium*/chemistry , Spin Labels*, Electron Spin Resonance Spectroscopy/methods ; Pyridines/chemistry |
| Περίληψη: | Highly selective and fast reactions at the thiol group of a cysteine-containing peptide or protein, giving a reduction-resistant linkage, are highly desirable for anchoring a paramagnetic label that enables structure determination with electron paramagnetic resonance and/or nuclear magnetic resonance spectroscopy. One possibility is the Michael addition of the thiol group onto a 4-vinylpyridine, which is a structural subunit of the labeling agent, e.g., of the complex 4-vinyl-PyMTA-Gd. This reaction, however, turned out to be too slow for broad applicability. If pyridine is exchanged for pyrimidine, this reaction becomes very fast while still being sufficiently chemoselective, as is demonstrated with reactions of the complexes 4-vinyl-PymiMTA-Ln with Ln = Gd and/or La, which contain a 4-vinylpyrimidine subunit, with cysteine, cysteine-containing oligoproline, and cysteine-containing thioredoxin. Furthermore, it was found that the complex PymiMTA-Gd is a suitable spin label for distance determination via double electron electron resonance spectroscopy. Interestingly, the EPR spectra of PyMTA-Gd and PymiMTA-Gd and their relaxation times are very similar. Obviously, the exchange of pyridine for pyrimidine has little effect on these relevant EPR spectroscopical properties. This indicates that other pyridine-containing Gd3+ complexes may be convertible in the same way to fast-reacting, ready-made spin labels while keeping their favorable EPR spectroscopical properties. |
| Substance Nomenclature: | K848JZ4886 (Cysteine) 0 (Spin Labels) AU0V1LM3JT (Gadolinium) 0 (Pyridines) |
| Entry Date(s): | Date Created: 20250926 Date Completed: 20251015 Latest Revision: 20260522 |
| Update Code: | 20260522 |
| DOI: | 10.1021/acs.bioconjchem.5c00358 |
| PMID: | 40999727 |
| Βάση Δεδομένων: | MEDLINE |
| ISSN: | 1520-4812 |
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| DOI: | 10.1021/acs.bioconjchem.5c00358 |