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Updated: Jun 15, 2026

Computational Prediction of Amino Acid Preferences of Potentially Multispecific Peptide-Binding Domains Involved in Protein-Protein Interactions
Published on: January 26, 2024
alpha-Amino-beta-hydroxy-gamma-lactam for constraining peptide Ser and Thr residue conformation
Daniel J St-Cyr1, Andrew G Jamieson, William D Lubell
1Departement de Chimie, Université de Montreal, C.P. 6128, Succursale Centre-Ville, Montreal, Québec H3C 3J7, Canada.
Abstract:
Alpha-amino-beta-hydroxy-gamma-lactam 1 is a peptide mimic in which the Ser/Thr residue omega-, psi-, and chi-dihedral angle geometry all are constrained by the 5-membered lactam ring. Lactams 1 were made by employing N-(Fmoc)oxiranylglycine 3 as a bis-electrophile in TFE with cat. BzOH to sequentially alkylate and acylate a variety of amino acid derivatives in one pot. Solid-phase synthesis of beta-hydroxy-gamma-lactam 8, an analogue of the IL-1 modulator 101.10, was achieved using this method for studying Ser/Thr geometry.
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