Solid-phase synthesis of NMe-IB-01212, a highly N-methylated cyclic peptide
| Autor: | Fernando Albericio, Eleonora Marcucci, Judit Tulla-Puche |
|---|---|
| Rok vydání: | 2011 |
| Předmět: |
Depsipeptide
chemistry.chemical_classification Molecular Structure Stereochemistry Organic Chemistry Peptide Biochemistry Methylation Cyclic peptide Acylation chemistry.chemical_compound Solid-phase synthesis chemistry Isomerism Cyclization Depsipeptides Trifluoroacetic acid Solid-Phase Synthesis Techniques Epimer Physical and Theoretical Chemistry |
| Zdroj: | Organic letters. 14(2) |
| ISSN: | 1523-7052 |
| Popis: | N-Methylation of peptides is an important synthetic tool in peptide-based medicinal chemistry. Herein, an optimized strategy for solid-phase synthesis of small but highly N-methylated cyclic peptides is described. The proposed route addresses several problems associated with the synthesis of peptides containing several sequential N-methyl-amino acids, such as in situ N-methylation, difficulty of acylation, epimerization, diketopiperazine formation, and stability at the NMe sites under trifluoroacetic acid exposure. The resulting NMe-IB-01212 exhibits micromolar activity and considerable stability. |
| Databáze: | OpenAIRE |
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