Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 86, Issue 17, Pages 12292-12299Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.1c01045
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Funding
- National Science Centre, Poland [UMO-2019/35/N/ST4/00477]
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A one-pot method for peptide cleavage and cyclization from a solid support has been developed, demonstrating feasibility through the synthesis of model short peptides. The entire peptide precursor synthesis can be fully automated without epimerization or dimerization.
We developed a one-pot method for peptide cleavage from a solid support via the N,S-acyl shift of N-2-[thioethyl]glycine and transthioesterification using external thiols to produce cyclic peptides through native chemical self-ligation with the N-terminal cysteine. The feasibility of this methodology is validated by the syntheses of model short peptides, including a tetrapeptide, the bicyclic sunflower trypsin inhibitor SFTI-1, and rhesus Theta-defensin RTD-1. Synthesis of the whole peptide precursor can be fully automated and proceeds without epimerization or dimerization.
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