Syntheses of Atypically Fluorinated Peptidyl Macrocycles through Sequential Vinylic Substitutions
| Autor: | Angel Mendoza, Tomoyuki Tsunemi, Salvador J. Bernardino, Patrick G. Harran, Christopher G. Jones |
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| Rok vydání: | 2019 |
| Předmět: |
Macrocyclic Compounds
Vinyl Compounds 010405 organic chemistry Chemistry Stereochemistry Peptidomimetic Tryptophan General Chemistry 010402 general chemistry 01 natural sciences Catalysis 0104 chemical sciences Serine Consensus sequence Humans Tyrosine Histidine Cysteine Asparagine Threonine Peptides |
| Zdroj: | Angewandte Chemie International Edition. 59:674-678 |
| ISSN: | 1521-3773 1433-7851 |
| DOI: | 10.1002/anie.201910136 |
| Popis: | Small peptides containing combinations of cysteine, tyrosine, histidine, and serine residues react with octafluorocyclopentene (OFCP) to afford atypically structured macrocycles through successive vinylic substitutions. The reactions proceed rapidly in air at 0 °C and are tolerant of spectating tryptophan, asparagine, glutamine, and threonine residues. Hexapeptides of consensus sequence YXCXXC displace four fluorine atoms from OFCP to generate fluorinated macrobicyclic compounds that display dual-turn surfaces. The method provides facile access to a wide range of previously unknown heterocyclic structures. |
| Databáze: | OpenAIRE |
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