Chiral imines 1a,b, already synthesized in our laboratory, were converted in good yield by reduction into the corresponding N-benzyl-gamma-lactams 2a,b. Desilylation followed by oxidation of the hydroxymethyl functionality gave the N-benzyl-beta-amino acids 7a,b in good yield and high purity. Starting from compound 7a, the corresponding beta-peptoid dimer 8 was prepared, together with its derivatives 9 and 10, this latter displaying conformational restriction about the peptide bond, as evidenced by 1H NMR data.
G. Martelli, A. Monsignori, M. Orena, S. Rinaldi, N. Castellucci, C. Tomasini (2012). Beta-Peptoids: synthesis of a novel dimer having a fully extended conformation. AMINO ACIDS, 43(5), 2005-2014 [10.1007/s00726-012-1275-1].
Beta-Peptoids: synthesis of a novel dimer having a fully extended conformation
MARTELLI, GIANLUCA;RINALDI, SAMUELE;CASTELLUCCI, NICOLA;TOMASINI, CLAUDIA
2012
Abstract
Chiral imines 1a,b, already synthesized in our laboratory, were converted in good yield by reduction into the corresponding N-benzyl-gamma-lactams 2a,b. Desilylation followed by oxidation of the hydroxymethyl functionality gave the N-benzyl-beta-amino acids 7a,b in good yield and high purity. Starting from compound 7a, the corresponding beta-peptoid dimer 8 was prepared, together with its derivatives 9 and 10, this latter displaying conformational restriction about the peptide bond, as evidenced by 1H NMR data.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
