title: β-Peptoids: synthesis of a novel dimer having a fully extended conformation.
abstract: Chiral imines 1a,b, already synthesized in our laboratory, were converted in good yield by reduction into the corresponding N-benzyl-γ-lactams 2a,b. Desilylation followed by oxidation of the hydroxymethyl functionality gave the N-benzyl-β-amino acids 5a,b in good yield and high purity. Starting from compound 6a, the corresponding β-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.
authors.affiliation: Di.S.V.A.-Chemistry, Polytechnic University of Marche, Via Brecce Bianche, 60131 Ancona, Italy. gmartell@univpm.it
authors.forename: Gianluca
authors.initials: G
authors.lastname: Martelli
authors.forename: Antonella
authors.initials: A
authors.lastname: Monsignori
authors.forename: Mario
authors.initials: M
authors.lastname: Orena
authors.forename: Samuele
authors.initials: S
authors.lastname: Rinaldi
authors.forename: Nicola
authors.initials: N
authors.lastname: Castellucci
authors.forename: Claudia
authors.initials: C
authors.lastname: Tomasini
mesh_terms: D000596:Amino Acids / Q000737:chemistry*; D019281:Dimerization; D007097:Imines / Q000737:chemistry*; D007769:Lactams / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D008968:Molecular Conformation; D010084:Oxidation-Reduction; D034444:Peptoids / Q000138:chemical synthesis*; D013237:Stereoisomerism
chemical_list: D000596:Amino Acids; D007097:Imines; D007769:Lactams; D034444:Peptoids