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

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The Chemistry of Benzotriazole Derivatives

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

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Authors and Affiliations

  1. Department of Chemistry and Physics, Georgia Regents University, 1120 15th Street SCI W3005, Augusta, GA, 30912, USA

    Thomas Albers, Armanda F. Gameiro & Iryna O. Lebedyeva

  2. Department of Chemistry and Biochemistry, University of Mississippi, Mississippi, MS, 38677, USA

    Davita L. Watkins

  3. Department of Organic and Biochemical Synthesis, Kherson National Technical University, Berislavs’ke Highway 24, Kherson, 73008, Ukraine

    V’yacheslav Povstyanoy & Mykhaylo V. Povstyanoy

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  1. Thomas Albers
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  2. Davita L. Watkins
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  4. V’yacheslav Povstyanoy
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  5. Mykhaylo V. Povstyanoy
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  6. Iryna O. Lebedyeva
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Correspondence to Iryna O. Lebedyeva .

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Editors and Affiliations

  1. Center for Integrated Technology and Organic Synthesis - CiTOS, Department of Chemistry, University of Liège, Liège, Belgium

    Jean-Christophe M. Monbaliu

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Albers, T., Watkins, D.L., Gameiro, A.F., Povstyanoy, V., Povstyanoy, M.V., Lebedyeva, I.O. (2015). Benzotriazole-Based Strategies Toward Peptidomimetics, Conjugates, and Other Peptide Derivatives. In: Monbaliu, JC. (eds) The Chemistry of Benzotriazole Derivatives. Topics in Heterocyclic Chemistry, vol 43. Springer, Cham. https://doi.org/10.1007/7081_2015_182

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