Macrocyclic peptides are important lead targets for pharmaceutical development, and methods for their synthesis have been an area of focused study by the peptide community for decades. Strategies that utilize a native chemical ligation (NCL)-like approach (i.e.; a cysteine-mediated macrocyclization) are particularly powerful because of the enhanced nucleophilicity and easily exploitable pKa differences of the Cys thiol vs. other potential nucleophiles. However, NCL methods, including Cys and non-Cys NCL followed by desulfurization have not employed industrially because of the unmanageable amount of waste generated due to dilution requirements and large excesses of phosphine and thiol reagents. This seminar will describe our recent efforts to minimize waste in both the cysteine-mediated cyclization of peptides and in the subsequent radical-mediated desulfurization process.

Trimming the waste-line in macrocyclic peptide synthesis: <i>N</i>-acyl urea cyclization and photodesulfurization

Macromolecular Chemistry: The Second Century

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ACS Spring 2020 National Meeting & Expo

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.

Trimming the waste-line in macrocyclic peptide synthesis: N-acyl urea cyclization and photodesulfurization