alpha-Amino-beta-hydroxy-gamma-lactam for constraining peptide Ser and Thr residue conformation.
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.
St-Cyr
Daniel J
DJ
Departement de Chimie, Université de Montreal, C.P. 6128, Succursale Centre-Ville, Montreal, Québec H3C 3J7, Canada.
Jamieson
Andrew G
AG
Lubell
William D
WD
D007769:Lactams / Q000737:chemistry*; D008968:Molecular Conformation; D010455:Peptides / Q000737:chemistry*; D012694:Serine / Q000737:chemistry*; D013912:Threonine / Q000737:chemistry*
D007769:Lactams; D010455:Peptides; D013912:Threonine; D012694:Serine