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Updated: May 23, 2026

Solid-phase Submonomer Synthesis of Peptoid Polymers and their Self-Assembly into Highly-Ordered Nanosheets
Published on: November 2, 2011
β-Peptoids: synthesis of a novel dimer having a fully extended conformation
Gianluca Martelli1, Antonella Monsignori, Mario Orena
1Di.S.V.A.-Chemistry, Polytechnic University of Marche, Via Brecce Bianche, 60131 Ancona, Italy. gmartell@univpm.it
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.
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