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Chemoselective synthesis of N-terminal cysteinyl thioesters via β,γ-C,S thiol-Michael addition
journal contribution
posted on 2023-08-25, 13:52 authored by Rita Petracca, Katherine A Bowen, Lauren McSweeney, Siobhan O'Flaherty, Vito Genna, Brendan Twamley, Marc DevocelleMarc Devocelle, Eoin M ScanlanDehydroalanine (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.
Funding
Science Foundation Ireland (SFI) under Grant Nos. 15/CDA/3310 & 16/RI/3737
Irish Research Council
History
Comments
This 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.9b01013Published Citation
Petracca 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 Date
24 April 2019External DOI
PubMed ID
31017793Department/Unit
- Chemistry
Research Area
- Chemistry and Pharmaceutical Sciences
Publisher
American Chemical Society (ACS)Version
- Accepted Version (Postprint)
