Chiral imines 1a,b, already synthesized in our laboratory, were converted in good yield by reduction into the corresponding N-benzyl-c-lactams 2a,b. Desilylation followed by oxidation of the hydroxymethyl functionality gave the N-benzyl-b-amino acids 5a,b in good yield and high purity. Starting from compound 6a, the corresponding b-peptoid dimer 8 was prepared, together with its derivatives 9 and 10, these latter displaying conformational restriction about the peptide bond, as evidenced by NMR data.
beta-Peptoids: synthesis of a novel dimer having a fully extendedconformation / Martelli, Gianluca; Monsignori, Antonella; Orena, Mario; Rinaldi, Samuele; Castellucci, N.; Tomasini, C. .. - In: AMINO ACIDS. - ISSN 1438-2199. - 43:5(2012), pp. 2005-2014. [10.1007/s00726-012-1275-1]
beta-Peptoids: synthesis of a novel dimer having a fully extendedconformation
MARTELLI, Gianluca;MONSIGNORI, ANTONELLA;ORENA, MARIO;RINALDI, SAMUELE;
2012-01-01
Abstract
Chiral imines 1a,b, already synthesized in our laboratory, were converted in good yield by reduction into the corresponding N-benzyl-c-lactams 2a,b. Desilylation followed by oxidation of the hydroxymethyl functionality gave the N-benzyl-b-amino acids 5a,b in good yield and high purity. Starting from compound 6a, the corresponding b-peptoid dimer 8 was prepared, together with its derivatives 9 and 10, these latter displaying conformational restriction about the peptide bond, as evidenced by NMR data.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
