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.
Beta-Peptoids: synthesis of a novel dimer having a fully extended conformation / G. Martelli; A. Monsignori; M. Orena; S. Rinaldi; N. Castellucci; C. Tomasini. - In: AMINO ACIDS. - ISSN 0939-4451. - STAMPA. - 43:5(2012), pp. 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.
