N-aminoimidazolidin-2-one peptidomimetics

Org Lett. 2014 Apr 18;16(8):2232-5. doi: 10.1021/ol500739k. Epub 2014 Apr 4.

Abstract

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.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkylation
  • Amino Acid Sequence
  • Aza Compounds / chemical synthesis
  • Aza Compounds / chemistry
  • Chemistry, Organic / methods
  • Lactams / chemical synthesis
  • Lactams / chemistry
  • Molecular Conformation
  • Molecular Structure
  • Oligopeptides / chemistry
  • Peptides / chemical synthesis*
  • Peptides / chemistry*
  • Peptidomimetics
  • Semicarbazones / chemistry*

Substances

  • Aza Compounds
  • Lactams
  • Oligopeptides
  • Peptides
  • Peptidomimetics
  • Semicarbazones
  • growth hormone releasing hexapeptide