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(Thio)diketopiperazines

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The Chemistry of Mycotoxins

Part of the book series: Progress in the Chemistry of Organic Natural Products ((POGRCHEM,volume 97))

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Abstract

The smallest cyclic peptides built from amino acids are the so-called diketopiperazines (DKP). In recent research, the DKPs and higher functionalized analogs – the thiodiketopiperazines (TDKP) – have become attractive due to their broad biological activity (390). The DKP or TDKP moiety can be found in a great variety of mycotoxins. Both DKPs and TDKPs can, for example, be isolated from Aspergillus, Candida, Chaetomium, Gliocladium, Penicillium, and Verticillium species (7, 390). The most common structural motifs A–D of this class of compounds are depicted in Fig. 10.1. Many of these natural products show C 2 symmetry, which means they consist of two identical amino acids (R = R′ in Fig. 10.1).

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Authors and Affiliations

  1. Karlsruhe Institute of Technology (KIT), Institute of Organic Chemistry – Institute of Toxicology and Genetics, 76131, Karlsruhe, Germany

    Stefan Bräse

  2. Karlsruhe Institute of Technology (KIT), Institute of Organic Chemistry, 76131, Karlsruhe, Germany

    Franziska Gläser, Carsten S. Kramer, Stephanie Lindner, Anna M. Linsenmeier, Kye-Simeon Masters, Anne C. Meister, Bettina M. Ruff & Sabilla Zhong

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Bräse, S. et al. (2013). (Thio)diketopiperazines. In: The Chemistry of Mycotoxins. Progress in the Chemistry of Organic Natural Products, vol 97. Springer, Vienna. https://doi.org/10.1007/978-3-7091-1312-7_10

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