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Synthetic Fermentation of β-peptide Macrocycles by Thiadiazole-Forming Ring-Closing Reactions

Abstract

Macrocyclic β-peptides were efficiently prepared using a thiadiazole-forming cyclization reaction between an α-ketoacid and a thiohydrazide. Synthetic fermentation was applied to generate mixtures of short β-peptides, which underwent Boc-deprotection/thiadiazole-forming macrocyclization under aqueous, acidic conditions to provide the cyclic products in a one-pot process. This reaction sequence proceeds from easily accessed initiator and monomer building blocks without the need for additional catalysts or reagents, enabling facile production of macrocyclic β-peptides, a relatively underexplored structural class.

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Publication details

The article was received on 25 Nov 2017, accepted on 05 Jan 2018 and first published on 08 Jan 2018


Article type: Edge Article
DOI: 10.1039/C7SC05057G
Citation: Chem. Sci., 2018, Accepted Manuscript
  • Open access: Creative Commons BY-NC license
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    Synthetic Fermentation of β-peptide Macrocycles by Thiadiazole-Forming Ring-Closing Reactions

    J. G. Hubert, I. A. Stepek, H. Noda and J. W. Bode, Chem. Sci., 2018, Accepted Manuscript , DOI: 10.1039/C7SC05057G

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