Solution-phase synthesis of novel seven-membered cyclic dipeptides containing α- and β-amino acids

Autor: C. Gabriela Avila-Ortiz, Erika Jiménez-González, Jorge Vargas-Caporali, Georges Dewynter, Eusebio Juaristi, Rodrigo González-Olvera
Rok vydání: 2012
Předmět:
Zdroj: Tetrahedron. 68:9842-9852
ISSN: 0040-4020
DOI: 10.1016/j.tet.2012.08.050
Popis: A convenient synthetic procedure for the preparation of seven-membered cyclic α,β-dipeptides is described. Following coupling of N-protected α-amino acids with N-substituted β-amino acid tert-butyl esters, that affords linear α,β-dipeptides, the protecting groups at the terminal functionalities were removed and the open-chain dipeptides were cyclized with phenylphosphonic dichloride, PhP(O)Cl2, to give the desired cyclic α,β-dipeptides in good yields. NMR studies, X-ray diffraction analysis, and DFT calculations provided evidence for the conformation adopted by these cyclic dipeptides in solution, in the solid-state, and in the gas phase.
Databáze: OpenAIRE