Chemoselective synthesis of N-terminal cysteinyl thioesters via β,γ-C,S thiol-Michael addition
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.
Science Foundation Ireland (SFI) under Grant Nos. 15/CDA/3310 & 16/RI/3737
Irish Research Council
CommentsThis document is the Accepted Manuscript version of a Published Work that appeared in final form in Organic Letters © 2019 American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see https://doi.org/10.1021/acs.orglett.9b01013
Published CitationPetracca R, et al. Chemoselective synthesis of N-terminal cysteinyl thioesters via β,γ-C,S thiol-Michael addition. Org Lett. 2019;21(9):3281-3285.
Publication Date24 April 2019
- Chemistry and Pharmaceutical Sciences
PublisherAmerican Chemical Society (ACS)
- Accepted Version (Postprint)