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The Chemistry of Benzotriazole Derivatives pp 67–94Cite as

Acylbenzotriazoles: New Allies for Short Linear and Cyclic Peptide Constructs

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Part of the book series: Topics in Heterocyclic Chemistry ((TOPICS,volume 43))

Abstract

Peptides and proteins have tremendous potential as medicinal drugs, but their potential has largely been untapped due to several problems such as their fast degradation by enzymes and limited bioavailability. Major advances in the development of peptide synthesis methods, availability of a wide array of coupling reagents and other augments have lowered the barrier to entry for peptide drugs. However, greater access to peptides and proteins is needed in order to realize the possibilities for diagnosing, treating and monitoring critical diseases. Acylbenzotriazoles are an expedient gateway to cyclic and difficult peptides. With this overview, we now describe the use of acylbenzotriazoles as allies for the construction of peptides and peptide conjugates. The efficacy of N-(protected-α aminoacyl)benzotriazoles for the preparation of an extensive range of enantiopure peptides with good yields and purities on solid-phase or in solution, as well as challenges encountered and the way forward is addressed in the chapter.

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  1. The Dow Chemical Company, 400 Arcola Road, Collegeville, PA, 19426, USA

    Danniebelle N. Haase

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  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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Haase, D.N. (2016). Acylbenzotriazoles: New Allies for Short Linear and Cyclic Peptide Constructs. In: Monbaliu, JC. (eds) The Chemistry of Benzotriazole Derivatives. Topics in Heterocyclic Chemistry, vol 43. Springer, Cham. https://doi.org/10.1007/7081_2015_199

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