ol500739k_si_001.pdf (6.85 MB)
N‑Aminoimidazolidin-2-one Peptidomimetics
journal contribution
posted on 2014-04-18, 00:00 authored by Ngoc-Duc Doan, Robert Hopewell, William D. LubellThe
synthesis of N-aminoimidazolidin-2-one (Aid)
peptidomimetics has been achieved by alkylation of the urea nitrogen
of a semicarbazone residue using ethylene bromide. The Aid scaffold
combines electronic and structural constraints to rigidify the peptide
backbone in the equivalent of an aza variant of a Freidinger–Veber
lactam. The syntheses and isolation of 25 Aid peptides, including
eight GHRP-6 analogues, are reported to demonstrate the utility of
this method for controlling conformation.