FIGURE

Fig. 2

ID

ZDB-FIG-260407-31

Publication

Chojnacki et al., 2026 - Click-to-Release Reactions for Tertiary Amines and Pyridines

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Fig. 2

Tetrazine-mediated release of tertiary amines from isocyanopropyl (ICPr) groups. (a) Synthesis of quaternary ammonium groups with ICPr-substituents by reacting tertiary amines with isocyanopropyl tosylate. (b) Concept of tertiary amine release from the ICPr group by reaction with tetrazine. (c) 1H NMR analysis of the release of N,N-dimethylbenzylamine (DMBA) from the isocyanopropyl precursor ICPr-DMBA (6 mM ICPr-DMBA, 18 mM DPTz, DMSO-d6/PBS-d, pH = 7.4, 9/1, 37 °C). (d) 19F NMR analysis of the release of N,N-dimethyl-4-trifluoromethylbenzylamine (DMFBA) from the ICPr precursor ICPr-DMFBA (2 mM ICPr-DMFBA, 18 mM PEG-Tz (see Chart 1 in the Supporting Information), DMSO-d6/PBS-d, 1/9, pH = 7.4, 37 °C). (e) Time dependence of DMFBA release by 19F NMR (2 mM ICPr-DMFBA, 20 mM PEG-Tz, 3 mM KF (internal standard), DMSO-d6/PBS-d, pH = 7.4, 1/9, 37 °C). (f) HPLC analysis of release of naphthalamide probe of tertiary amine from ICPr precursor (ICPr-TA-NA) (2 mM ICPr-TA-NA, 20 mM PEG-Tz, DMSO/PBS, 1/9, pH = 7.4, 37 °C).

Expression Data

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Antibody Labeling

Phenotype Data

Phenotype Detail

Acknowledgments

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