Chemoselective synthesis of N-terminal cysteinyl thioesters via β, γ-C, S thiol-michael addition

R Petracca, KA Bowen, L McSweeney… - Organic …, 2019 - ACS Publications
R Petracca, KA Bowen, L McSweeney, S O'Flaherty, V Genna, B Twamley, M Devocelle…
Organic letters, 2019ACS Publications
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.
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.
ACS Publications
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