Tritium O-Methylation of N-Alkoxy Maleimide Derivatives as Labeling Reagents for Biomolecules
| Autor: | Thorsten Muser, Martin R. Edelmann |
|---|---|
| Rok vydání: | 2021 |
| Předmět: |
Biomedical Engineering
Pharmaceutical Science Bioengineering 02 engineering and technology 01 natural sciences chemistry.chemical_compound In vivo Maleimide Pharmacology chemistry.chemical_classification 010405 organic chemistry Biomolecule Organic Chemistry Methylation 021001 nanoscience & nanotechnology Combinatorial chemistry 0104 chemical sciences chemistry Reagent Alkoxy group Tritium Specific activity 0210 nano-technology Biotechnology |
| Zdroj: | Edelmann, M R & Muser, T 2021, ' Tritium O-Methylation of N-Alkoxy Maleimide Derivatives as Labeling Reagents for Biomolecules ', Bioconjugate Chemistry, vol. 32, no. 5, pp. 1027-1033 . https://doi.org/10.1021/acs.bioconjchem.1c00202 |
| ISSN: | 1520-4812 1043-1802 |
| DOI: | 10.1021/acs.bioconjchem.1c00202 |
| Popis: | An efficient procedure to access tritium-labeled maleimide derivatives in a high specific activity has been developed. N-Substituted maleimides containing the hydroxy functionality are O-methylated in a three-step synthesis route, including (1) Diels-Alder protection of the maleimide core, (2) O-methylation by the use of commercially available [3H]methyl nosylate, and (3) deprotection by retro-Diels-Alder reaction. With our procedure, N-hydroxyalkyl maleimide derivatives can be labeled in overall radiochemical yields of 13-15% and in >98% radiochemical purity. The major advantage of N-alkoxy maleimides in comparison to N-alkylated maleimides such as N-ethylmaleimide is their lower volatility, which enables safer handling with respect to radiation-safety protection. Tritium-labeled maleimide building blocks allow subsequent Michael-type conjugation reactions of thiol-containing biomolecules for mechanistic in vitro or in vivo studies. |
| Databáze: | OpenAIRE |
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