Semisynthetic head-to-tail cyclized peptides obtained by combining proteintrans-splicing and intramolecular expressed protein ligation
| Autor: | Henning D. Mootz, Shubhendu Palei |
|---|---|
| Rok vydání: | 2021 |
| Předmět: |
0303 health sciences
Natural product 010405 organic chemistry Stereochemistry Trypsin inhibitor Trans-splicing Metals and Alloys General Chemistry 01 natural sciences Semisynthesis Catalysis 0104 chemical sciences Surfaces Coatings and Films Electronic Optical and Magnetic Materials 03 medical and health sciences chemistry.chemical_compound chemistry Intramolecular force Materials Chemistry Ceramics and Composites Peptide bond Intein Ligation 030304 developmental biology |
| Zdroj: | Chemical Communications. 57:4194-4197 |
| ISSN: | 1364-548X 1359-7345 |
| Popis: | A dual-intein approach for the preparation of head-to-tail macrocyclic peptides is reported, where synthetic and genetically encoded fragments are ligated by two native peptide bonds. A split intein ligates the synthetic and genetically encoded peptides via protein trans-splicing and is followed by intramolecular cyclization through an expressed protein ligation step mediated with a cis-intein. We identified a suitable pair of orthogonal inteins and optimized the conditions for a one-pot cyclization protocol. We report the semisynthesis of model macrocyles with various ring sizes and of the natural product sunflower trypsin inhibitor (SFTI) along with its ornithine analog. |
| Databáze: | OpenAIRE |
| Externí odkaz: |
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