1333014-20-2Relevant articles and documents
Chemoselective Synthesis of N-Terminal Cysteinyl Thioesters via β,γ-C,S Thiol-Michael Addition
Petracca, Rita,Bowen, Katherine A.,McSweeney, Lauren,O'Flaherty, Siobhan,Genna, Vito,Twamley, Brendan,Devocelle, Marc,Scanlan, Eoin M.
, p. 3281 - 3285 (2019)
Dehydroalanine (ΔAla) is a highly electrophilic residue that can react efficiently with sulfur nucleophiles to furnish cysteinyl analogues. Herein, we report an efficient synthesis of N-terminal cysteinyl thioesters, suitable for S,N-acyl transfer, based on β,γ-C,S thiol-Michael addition. Both ionic and radical-based methodologies were found to be efficient for this process.