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Mimicry of the Backbone and Side-Chain Geometry of Peptide Turns: Synthesis of Novel 4-Substituted Indolizidin-9-one Amino Acids

  • Jérôme Cluzeau
  • William D. Lubell
Part of the American Peptide Symposia book series (APSY, volume 7)

Abstract

Indolizidinone amino acids have served as ß-turn mimics for exploring conformation-activity relationships in natural peptides [1]. Focus has been particularly placed on mirnicry of peptides containing aromatic residues within turn regions because of their importance in various recognition events. For example, 4- and 7-benzyl-indolizidin-2-one amino acid analogs 1 and 2 have been respectively used to synthesize ligands of the tachykinin and opioid receptors [2,3]. Similarly, indolizidin-9-one amino acid 3 has served in the synthesis of potent gramicidin S antibiotic peptides [4]. Interested in expanding the variety of indolizidinone amino acids possessing aromatic side-chains, we have now developed a new means for synthesizing 4-aryl-indolizidin-9-one amino acids 4.

Keywords

Amino Acid Analog Amino Ester Turn Region American Peptide Society Convex Configuration 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

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Copyright information

© Springer Science+Business Media Dordrecht 2001

Authors and Affiliations

  • Jérôme Cluzeau
    • 1
  • William D. Lubell
    • 1
  1. 1.Département de ChimieUniversité de MontréalMontréalCanada

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