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Updated: Sep 26, 2026

Synthesis of Protein Bioconjugates via Cysteine-maleimide Chemistry
Published on: July 20, 2016
Syntheses and biological properties of cysteine-reactive epibatidine derivatives
Christian Che1, Grégory Petit, Florence Kotzyba-Hibert
1Laboratoire de Chimie Bioorganique, UMR 7514 CNRS, Faculté de Pharmacie, Université Louis Pasteur Strasbourg BP 24, 67401 Illkirch, cedex France.
Abstract:
The synthesis of epibatidine derivatives modified at the 2-position of the pyridine or pyrimidine rings by reactive functions are described for potential irreversible site-directed coupling reactions on cysteine mutants of neuronal nicotinic acetylcholine receptors. An improved synthesis of the 7-azabicyclo[2,2,1]hepta-2,5-diene key intermediate has been developed to allow reproducible syntheses of the epibatidine derivatives. Binding tests and electrophysiological experiments allowed to select the 2-substituted alpha-chloroacetamido 13 and the chloropyrimidine derivative 11 as potential site-directed probes for the epibatidine binding site.
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