| Autor: |
Matulevičiūtė, Gita, Kleizienė, Neringa, Račkauskienė, Greta, Martynaitis, Vytas, Bieliauskas, Aurimas, Šachlevičiūtė, Urtė, Jankauskas, Rokas, Bartkus, Martynas R., Sløk, Frank A., Šačkus, Algirdas |
| Přispěvatelé: |
RSC (Royal Society of Chemistry) Publishing Home |
| Jazyk: |
angličtina |
| Rok vydání: |
2023 |
| Popis: |
In this study, we prepared a series of new N-(aminocycloalkylene)amino acid derivatives for use in chiral building blocks. The method was based on the conversion of enantiopure a-hydroxy acid esters into the corresponding chiral triflate esters, which were displaced by a nucleophilic substitution SN2 reaction with aminopyrrolidine and aminopiperidine derivatives, and the inversion of the configuration to give methyl 2-[(Boc-amino)cycloamin-1-yl]alkanoates with good yield and high enantiomeric and diastereomeric purity. Synthesized 2-[(Boc-amino)piperidin-1-yl]propanoates combined with ethyl L-phenylalaninate gave new chiral N-Boc- and N-nosyl-dipeptides containing a piperidine moiety. The structures were elucidated by 1H-, 13C-, and 15N-NMR spectroscopy, high-resolution mass spectrometry, and X-ray crystallography analyses. |
| Databáze: |
OpenAIRE |
| Externí odkaz: |
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