A study of the cis–trans isomerization preference of N-alkylated peptides containing phosphorus in the side chain and backbone
| Autor: | Alexander F. de la Torre, Akbar Ali, Julio Caballero, Erix W. Hernández-Rodríguez, Ana L. Montero-Alejo, Claudio A. Jiménez, Francisco M. Muñiz, Odette Concepcion, Julio Belmar, José Luis Velázquez-Libera |
|---|---|
| Rok vydání: | 2019 |
| Předmět: |
Stereochemistry
Isocyanide 02 engineering and technology General Chemistry Alkylation 010402 general chemistry 021001 nanoscience & nanotechnology 01 natural sciences Phosphonate Catalysis Cis trans isomerization 0104 chemical sciences chemistry.chemical_compound chemistry Materials Chemistry Side chain Amine gas treating 0210 nano-technology Isomerization Cis–trans isomerism |
| Zdroj: | New Journal of Chemistry. 43:12804-12813 |
| ISSN: | 1369-9261 1144-0546 |
| DOI: | 10.1039/c9nj02234a |
| Popis: | The current work provides a study on the cis–trans isomerization behaviour of N-alkylated peptides decorated with phosphonate ester groups. A Ugi four-component reaction was chosen for the synthesis of N-alkylated peptides, where almost only the cis isomer was detected when the phosphonate ester group was incorporated as an amine component in the side chain. However, the phosphonate ester group inserted in the backbone, as an isocyanide component, leads preferably to the trans isomer of this kind of peptides. The diverse behaviour of cis–trans isomerization has been explained via spectroscopic nuclear magnetic resonance analysis and computational calculations. |
| Databáze: | OpenAIRE |
| Externí odkaz: |
|