| Title |
Facile synthesis of new N-(aminocycloalkylene) amino acid compounds using chiral triflate esters with N-Boc-aminopyrrolidines and N-Bocaminopiperidines / |
| Authors |
Matulevičiūtė, Gita ; Kleizienė, Neringa ; Račkauskienė, Greta ; Martynaitis, Vytas ; Bieliauskas, Aurimas ; Šachlevičiūtė, Urtė ; Jankauskas, Rokas ; Bartkus, Martynas R ; Sløk, Frank A ; Šačkus, Algirdas |
| DOI |
10.1039/d3ra03060a |
| Full Text |
|
| Is Part of |
RSC advances.. Cambridge : Royal society of chemistry. 2023, vol. 13, iss. 31, p. 21570-21586.. ISSN 2046-2069 |
| Abstract [eng] |
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. |
| Published |
Cambridge : Royal society of chemistry |
| Type |
Journal article |
| Language |
English |
| Publication date |
2023 |
| CC license |
|
