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Issue 8, 2018
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Synthetic fermentation of β-peptide macrocycles by thiadiazole-forming ring-closing reactions

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Abstract

Macrocyclic β-peptides were efficiently prepared using a thiadiazole-forming cyclization reaction between an α-ketoacid and a thiohydrazide. The linear β-peptide precursors were assembled from isoxazolidine monomers by α-ketoacid-hydroxylamine (KAHA) ligations with a bifunctional initiator – a process we have termed ‘synthetic fermentation’ due to the analogy of producing natural product-like molecules from simpler building blocks. The linear synthetic fermentation products 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.

Graphical abstract: Synthetic fermentation of β-peptide macrocycles by thiadiazole-forming ring-closing reactions

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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., 2018,9, 2159-2167
  • 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, 9, 2159
    DOI: 10.1039/C7SC05057G

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