Diketopiperazine
Diketopiperazines (DKP) are a class of cyclic organic compounds that result from peptide bonds between two amino acids to form a lactam. They are the smallest possible cyclic peptides.
A diketopiperazine was the first peptide to have its complete three-dimensional structure described, in work undertaken at Caltech by Robert Corey in the 1930s. Corey studied the cyclic anhydride of the dipeptide glycylglycine.[1]
Diketopiperazines are commonly biosynthesized from amino acids by different organisms, including mammals, and are considered to be secondary metabolites.[2] Some protease enzymes, such as dipeptidyl peptidases, cleave the terminal ends of proteins to generate dipeptides which naturally cyclize to form diketopiperazines.
Due to their rigid structure, chiral nature, and varied side chains, diketopiperazines are an attractive scaffold for drug design.[2] Both natural and synthetic diketopiperazines have a wide variety of biological activities including antitumor,[3] antiviral,[4] antifungal[5] and antibacterial[6] activities.
References
Cite error: Invalid <references> tag;
parameter "group" is allowed only.
<references />, or <references group="..." />fr:Dioxopipérazine it:Dichetopiperazine
ja:ジケトピペラジン類- ↑ Corey, Robert B. (1938). "Crystal structure of diketopiperazine". Journal of the American Chemical Society. 60: 1598–1604. doi:10.1021/ja01274a023.
- ↑ 2.0 2.1 Maristela B. Martins and Ivone Carvalho (2007). "Diketopiperazines: biological activity and synthesis". Tetrahedron. 63: 9923–9932. doi:10.1016/j.tet.2007.04.105.
- ↑ Nicholson, B.; Lloyd, GK; Miller, BR; Palladino, MA; Kiso, Y; Hayashi, Y; Neuteboom, ST (2006). "NPI-2358 is a tubulin-depolymerizing agent: in-vitro evidence for activity as a tumor vascular-disrupting agent". Anti-Cancer Drugs. 17 (1): 25. doi:10.1097/01.cad.0000182745.01612.8a. PMID 16317287.
- ↑ Sinha, Sarika; Srivastava, Richa; De Clercq, Erik; Singh, Ramendra K. (2004). "Synthesis and Antiviral Properties of Arabino and Ribonucleosides of 1,3-Dideazaadenine, 4-Nitro-1,3-dideazaadenine and Diketopiperazine". Nucleosides, Nucleotides & Nucleic Acids. 23 (12): 1815–1824. doi:10.1081/NCN-200040614.
- ↑ Houston, Douglas R.; Synstad, Bjornar; Eijsink, Vincent G. H.; Stark, Michael J. R.; Eggleston, Ian M.; van Aalten, Daan M. F. (2004). "Structure-Based Exploration of Cyclic Dipeptide Chitinase Inhibitors". Journal of Medicinal Chemistry. 47 (23): 5713–5720. doi:10.1021/jm049940a. PMID 15509170.
- ↑ Kwon, Oh Sung; Park, Sang Ho; Yun, Bong-Sik; Pyun, Yu Ryang; Kim, Chang-Jin (2000). "Cyclo(dehydroala-L-Leu), an a-glucosidase inhibitor from Penicillium sp. F70614". Journal of Antibiotics. 53 (9): 954–958. PMID 11099229.
