alpha-Amino-beta-hydroxy-gamma-lactam for Constraining Peptide Ser and Thr Residue Conformation

作者：St Cyr Daniel J; Jamieson Andrew G; Lubell William D^*

来源：Organic Letters, 2010, 12(8): 1652-1655.

DOI：10.1021/ol1000582

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.

• 出版日期2010-4-16