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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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Supplementary files

Article information


Submitted
25 Nov 2017
Accepted
05 Jan 2018
First published
08 Jan 2018

This article is Open Access
All publication charges for this article have been paid for by the Royal Society of Chemistry

Chem. Sci., 2018,9, 2159-2167
Article type
Edge Article

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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