FIGURE

Fig. 6

ID

ZDB-FIG-260407-35

Publication

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

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Fig. 6

Evidence for the mechanism of the TzMe-removal from tertiary amines and pyridines by tert-butyl isonitrile (tBuNC). (a) 1H NMR spectrum of the side product isolated from the reaction of TzMe-Py with tBuNC. (b) X-ray crystal structure of the side product identifies it as 3-tert-butyl-4-(tert-butylamino)-1H-pyrazole-5-carbaldehyde. (c) Lewis structure of 3-tert-butyl-4-(tert-butylamino)-1H-pyrazole-5-carbaldehyde. (d) Orthogonal reactivity of primary (TMS-MeNC) and tertiary (tBuNC) isonitriles to TzMe groups on ammonium or carbamate groups. (e) Different release pathways for leaving groups from TzMe derivatives. Phenols and carbamates are efficiently released upon reaction with primary isonitriles from the 4-aminopyrazole derivative, but reaction with tertiary isonitriles forms a stable adduct. In contrast, the aminopyrazole derivative formed by TzMe groups with tertiary amine and pyridine leaving groups upon reaction with primary isonitriles is stable, whereas reaction with tertiary isonitriles releases the leaving groups from an earlier intermediate together with the release of 3-tert-butyl-4-(tert-butylamino)-1H-pyrazole-5-carbaldehyde through a distinct mechanism.

Expression Data

Expression Detail

Antibody Labeling

Phenotype Data

Phenotype Detail

Acknowledgments

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