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

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Peptidomimetics I

Part of the book series: Topics in Heterocyclic Chemistry ((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.

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Authors and Affiliations

  1. Département de Chimie, Université de Montréal, C.P. 6128, Succursale Centre-Ville, Montreal, QC, Canada, H3C 3J7

    Daniel J. St-Cyr, Yésica García-Ramos, Ngoc-Duc Doan & William D. Lubell

  2. Institute for Research in Immunology and Cancer, Université de Montréal, Pavillon Marcelle-Coutu, 2950 chemin de Polytechnique, Montreal, QC, Canada, H3T 1J4

    Daniel J. St-Cyr

  3. NuChem Therapeutics Inc., 6100 Royalmount Ave, Montreal, QC, Canada, H4P 2R2

    Yésica García-Ramos

  4. Department of Chemistry, Massachusetts Institute of Technology, 77 Massachusetts Ave, Cambridge, MA, 02139, USA

    Ngoc-Duc Doan

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    William D. Lubell

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St-Cyr, D.J., García-Ramos, Y., Doan, ND., Lubell, W.D. (2017). Aminolactam, N-Aminoimidazolone, and N-Aminoimdazolidinone Peptide Mimics. In: Lubell, W. (eds) Peptidomimetics I. Topics in Heterocyclic Chemistry, vol 48. Springer, Cham. https://doi.org/10.1007/7081_2017_204

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