Journal article
Synthetic fermentation of β-peptide macrocycles by thiadiazole-forming ring-closing reactions.
- Hubert JG Laboratorium für Organische Chemie , Department of Chemistry and Applied Biosciences , ETH Zürich , Zürich , Switzerland 8093 . Email: bode@org.chem.ethz.ch ; http://www.bode.ethz.ch.
- Stepek IA Laboratorium für Organische Chemie , Department of Chemistry and Applied Biosciences , ETH Zürich , Zürich , Switzerland 8093 . Email: bode@org.chem.ethz.ch ; http://www.bode.ethz.ch.
- Noda H Institute of Microbial Chemistry (Bikaken) , 3-14-23 Kamiosaki, Shinagawa-ku , Tokyo 141-0021 , Japan.
- Bode JW Laboratorium für Organische Chemie , Department of Chemistry and Applied Biosciences , ETH Zürich , Zürich , Switzerland 8093 . Email: bode@org.chem.ethz.ch ; http://www.bode.ethz.ch.
- 2018-05-03
Published in:
- Chemical science. - 2018
English
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.
- Language
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- English
- Open access status
- gold
- Identifiers
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- DOI 10.1039/c7sc05057g
- PMID 29719689
- Persistent URL
- https://roar.hep-bejune.ch/global/documents/3697
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