Ynamide-Mediated Thiopeptide Synthesis
© 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim..
Exploration of the full potential of thioamide substitution as a tool in the chemical biology of peptides and proteins has been hampered by insufficient synthetic strategies for the site-specific introduction of a thioamide bond into a peptide backbone. A novel ynamide-mediated two-step strategy for thiopeptide bond formation with readily available monothiocarboxylic acids as thioacyl donors is described. The α-thioacyloxyenamide intermediates formed from the ynamides and monothiocarboxylic acids can be purified, characterized, and stored. The balance between their activity and stability enables them to act as effective thioacylating reagents to afford thiopeptide bonds under mild reaction conditions. Amino acid functional groups such as OH, CONH2 , and indole NH groups need not be protected during thiopeptide synthesis. The modular nature of this strategy enables the site-specific incorporation of a thioamide bond into peptide backbones in both solution and the solid phase.
| Medienart: |
E-Artikel |
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| Erscheinungsjahr: |
2019 |
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| Erschienen: |
2019 |
| Enthalten in: |
Zur Gesamtaufnahme - volume:58 |
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| Enthalten in: |
Angewandte Chemie (International ed. in English) - 58(2019), 5 vom: 28. Jan., Seite 1382-1386 |
| Sprache: |
Englisch |
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| Beteiligte Personen: |
Yang, Jinhua [VerfasserIn] |
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| Links: |
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| Themen: |
Amides |
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| Anmerkungen: |
Date Completed 04.08.2020 Date Revised 04.08.2020 published: Print-Electronic Citation Status MEDLINE |
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| doi: |
10.1002/anie.201811586 |
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| funding: |
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| Förderinstitution / Projekttitel: |
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| PPN (Katalog-ID): |
NLM290361818 |
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| 520 | |a © 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim. | ||
| 520 | |a Exploration of the full potential of thioamide substitution as a tool in the chemical biology of peptides and proteins has been hampered by insufficient synthetic strategies for the site-specific introduction of a thioamide bond into a peptide backbone. A novel ynamide-mediated two-step strategy for thiopeptide bond formation with readily available monothiocarboxylic acids as thioacyl donors is described. The α-thioacyloxyenamide intermediates formed from the ynamides and monothiocarboxylic acids can be purified, characterized, and stored. The balance between their activity and stability enables them to act as effective thioacylating reagents to afford thiopeptide bonds under mild reaction conditions. Amino acid functional groups such as OH, CONH2 , and indole NH groups need not be protected during thiopeptide synthesis. The modular nature of this strategy enables the site-specific incorporation of a thioamide bond into peptide backbones in both solution and the solid phase | ||
| 650 | 4 | |a Journal Article | |
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| 700 | 1 | |a Wang, Changliu |e verfasserin |4 aut | |
| 700 | 1 | |a Xu, Silin |e verfasserin |4 aut | |
| 700 | 1 | |a Zhao, Junfeng |e verfasserin |4 aut | |
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