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Arbour, Christine A; Belavek, Kayla J; Tariq, Rooha; Mukherjee, Subha; Tom, Janine K; Isidro-Llobet, Albert; Kopach, Michael E; Stockdill, Jennifer L
Journal of organic chemistry, 01/2019, Letnik: 84, Številka: 2Journal Article
We establish herein conditions for the cyclization of unprotected N-acyl urea-linked peptides to form macrocyclic peptides mediated by N-terminal cysteine. We report a detailed investigation of the parameters of the reaction, including variation of the reaction conditions, the C-terminal residue, and the macrocycle size. C-Terminal epimerization was not observed. The synthesis of macrocyclic targets ranging from tetrapeptides to the disulfide-linked 14-mer, sunflower trypsin inhibitor 1 are demonstrated. For most substrates, hydrolysis and head-to-tail dimer formation are avoided.
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JCR | SNIP | JCR | SNIP | JCR | SNIP | JCR | SNIP |
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