N-aminoimidazolidin-2-one peptidomimetics.
The 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.
Département de Chimie, Université de Montréal , C.P. 6128, Succursale Centre-Ville, Montréal, Québec Canada H3C 3J7.
Ngoc-Duc
ND
Doan
Robert
R
Hopewell
William D
WD
Lubell
D000478:Alkylation; D000595:Amino Acid Sequence; D001372:Aza Compounds / Q000138:chemical synthesis / Q000737:chemistry; D002625:Chemistry, Organic / Q000379:methods; D007769:Lactams / Q000138:chemical synthesis / Q000737:chemistry; D008968:Molecular Conformation; D015394:Molecular Structure; D009842:Oligopeptides / Q000737:chemistry; D010455:Peptides / Q000138:chemical synthesis* / Q000737:chemistry*; D057786:Peptidomimetics; D012664:Semicarbazones / Q000737:chemistry*
D001372:Aza Compounds; D007769:Lactams; D009842:Oligopeptides; D010455:Peptides; D057786:Peptidomimetics; D012664:Semicarbazones; C041048:growth hormone releasing hexapeptide