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Benzotriazole-Based Strategies Toward Peptidomimetics, Conjugates, and Other Peptide Derivatives

  • Thomas Albers
  • Davita L. Watkins
  • Armanda F. Gameiro
  • V’yacheslav Povstyanoy
  • Mykhaylo V. Povstyanoy
  • Iryna O. LebedyevaEmail author
Chapter
Part of the Topics in Heterocyclic Chemistry book series (TOPICS, volume 43)

Abstract

Benzotriazole-mediated routes to peptidomimetics and peptide conjugates have been discussed in detail. The Katritzky group developed a benzotriazole methodology toward the activation of carbonyl groups of amino acids and modified analogs, which allowed the synthesis of cyclic peptides, azapeptides, azidopeptides, aminoxypeptides, oxyazapeptides, depsipeptides, and isopeptides. High-yielding reactions of N-, O-, S-, and C-acylated nucleophiles with activated aminoacyl or peptidoyl benzotriazole derivatives have also been reported. Benzotriazole methodology enabled the efficient incorporation of bioactive moieties into peptides, peptidomimetics, amino acids, and other carbonyl-containing compounds. Predominant number of reported products retained chiral purity. Some of the products displayed promising biological activities such as anticancer and antibacterial activity along with the improved stability under physiological conditions.

Keywords

Acylation Benzotriazole Conjugate Coupling Cyclic peptides Peptidomimetic 

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Copyright information

© Springer International Publishing Switzerland 2015

Authors and Affiliations

  • Thomas Albers
    • 1
  • Davita L. Watkins
    • 2
  • Armanda F. Gameiro
    • 1
  • V’yacheslav Povstyanoy
    • 3
  • Mykhaylo V. Povstyanoy
    • 3
  • Iryna O. Lebedyeva
    • 1
    Email author
  1. 1.Department of Chemistry and PhysicsGeorgia Regents UniversityAugustaUSA
  2. 2.Department of Chemistry and BiochemistryUniversity of MississippiMississippiUSA
  3. 3.Department of Organic and Biochemical SynthesisKherson National Technical UniversityKhersonUkraine

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