A New and Useful Method for the Macrocyclization of Linear Peptides
| Autor: | Chris Limberakis, David W. Piotrowski, Patrick B. Mullins, Allyn T. Londregan, Kathleen A. Farley |
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| Rok vydání: | 2012 |
| Předmět: |
Models
Molecular chemistry.chemical_classification Molecular Structure Chemistry Stereochemistry Lysine Organic Chemistry Chemistry Organic Phosphonium salt Substrate (chemistry) Peptides Cyclic Biochemistry Amino acid chemistry.chemical_compound Cyclization Vancomycin Intramolecular force Side chain Imidazole Histidine Physical and Theoretical Chemistry Peptides |
| Zdroj: | Organic Letters. 14:2890-2893 |
| ISSN: | 1523-7052 1523-7060 |
| Popis: | A new and useful procedure for the macrocyclization of linear peptides is described. The natural amino acid side chains of tyrosine (phenol), lysine (alkylamine), and histidine (imidazole) react in an intramolecular fashion with a pendent pyridine-N-oxide-carboxamide, which is selectively activated by the phosphonium salt, PyBroP. The reaction is mild, rapid, and efficient with a potentially large substrate scope. Multiple examples are provided with full characterization and analyses, including a novel aza-variant of the C-O-D ring system of vancomycin. |
| Databáze: | OpenAIRE |
| Externí odkaz: |
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