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Amino acids and peptides as reactants in multicomponent reactions: modification of peptides with heterocycle backbones through combinatorial chemistry

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Abstract

In this study, amino acids and peptides were used as reactants in a Hantzsch multicomponent reaction in order to synthesize new structurally diverse molecules containing these synthons. As well, an applicable strategy for modification of these natural molecules with heterocycle backbones such as pyrimidine, xanthene and acridine is introduced. Using this method, a set of new amino acid- and peptide-functionalized heterocycles were synthesized in good to excellent yields under mild conditions. Furthermore, carbohydrates were used as substrates in the synthesis of some derivatives. Overall, this methodology allows the possibility of synthesis of large numbers of natural product-based libraries, using amino acids, peptides and carbohydrates through combinatorial chemistry.

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Acknowledgements

The financial support from the Research Councils of Shiraz University is gratefully acknowledged.

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Authors and Affiliations

  1. Department of Chemistry, College of Sciences, Shiraz University, Shiraz, 71454, Iran

    Maryam Nourisefat, Farhad Panahi & Ali Khalafi-Nezhad

  2. Mahshahr Campus, Amirkabir University of Technology, Mahshahr, Iran

    Farhad Panahi

  3. Department of Polymer Engineering and Color Technology, Amirkabir University of Technology, Tehran, Iran

    Farhad Panahi

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  1. Maryam Nourisefat
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Correspondence to Farhad Panahi or Ali Khalafi-Nezhad.

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Nourisefat, M., Panahi, F. & Khalafi-Nezhad, A. Amino acids and peptides as reactants in multicomponent reactions: modification of peptides with heterocycle backbones through combinatorial chemistry. Mol Divers 23, 317–331 (2019). https://doi.org/10.1007/s11030-018-9861-0

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