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Aminolactam, N-Aminoimidazolone, and N-Aminoimdazolidinone Peptide Mimics

  • Daniel J. St-Cyr
  • Yésica García-Ramos
  • Ngoc-Duc Doan
  • William D. Lubell
Chapter
Part of the Topics in Heterocyclic Chemistry book series (TOPICS, volume 48)

Abstract

Among strategies for constraining peptide conformation, the application of 3-amino-γ-lactam (Agl) analogs, the so-called Freidinger-Veber lactams, has played a prominent role in studies of biologically active peptide conformation. Tethering an amino acid side chain to the nitrogen of its neighboring C-terminal residue within a peptide, such lactams constrain backbone ψ- and ω-dihedral angles, as well as side chain χ-torsion angles to induce turn conformation. Reviewing various α-amino lactam analogs as well as their aza-counterparts, the so-called N-amino imidazolinone (Nai) and N-amino imidazolidinone (Aid) residues, this chapter focuses specifically on the synthesis, conformational analysis, and applications of the 5-membered ring congeners and their variants bearing ring substituents.

Keywords

Amino-imidazolidinone Amino-imidazolinone Amino-lactam Azabicycloalkanone Azapeptide Conformation Dipeptide mimic Interleukin-1 Medicinal chemistry Peptidomimetic 

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Copyright information

© Springer International Publishing Switzerland 2017

Authors and Affiliations

  • Daniel J. St-Cyr
    • 1
    • 2
  • Yésica García-Ramos
    • 1
    • 3
  • Ngoc-Duc Doan
    • 1
    • 4
  • William D. Lubell
    • 1
  1. 1.Département de ChimieUniversité de MontréalMontrealCanada
  2. 2.Institute for Research in Immunology and CancerUniversité de MontréalMontrealCanada
  3. 3.NuChem Therapeutics Inc.MontrealCanada
  4. 4.Department of ChemistryMassachusetts Institute of TechnologyCambridgeUSA

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