Back Diketopiperazine German 2,5-Piperazino-duketono Esperanto Dioxopipérazine French Diketopiperazinok Hungarian Dichetopiperazine Italian 2,5-ジケトピペラジン Japanese 2,5-diketopiperazine Dutch Glycinanhydrid Swedish
 | The article's lead section may need to be rewritten. The reason given is: This article is not about the compound 2,5-diketopiperazine but the group of 2,5-diketopiperazines. (June 2024) |
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| Names | |
|---|---|
| IUPAC name
2,5-Piperazinedione
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| Preferred IUPAC name
Piperazine-2,5-dione | |
| Other names
Cyclic dipeptides, cyclo-dipeptides, DKPs, CDPs 2,5 dioxopiperazines (DOPs), dipeptide anhydrides
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| Identifiers | |
3D model (JSmol)
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| 112112 | |
| ChEBI | |
| ChEMBL | |
| ChemSpider | |
| EC Number |
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| 217756 | |
| KEGG | |
PubChem CID
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| UNII | |
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| Properties | |
| C4H6N2O2 | |
| Molar mass | 114.104 g·mol−1 |
| Melting point | 311–312 °C (592–594 °F; 584–585 K) |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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2,5-Diketopiperazine is an organic compound with the formula (NHCH2C(O))2. The compound features a six-membered ring containing two amide groups at opposite positions in the ring. It was first compound containing a peptide bond to be characterized by X-ray crystallography in 1938.[1] It is the parent of a large class of 2,5-Diketopiperazines (2,5-DKPs) with the formula (NHCH2(R)C(O))2 (R = H, CH3, etc.). They are ubiquitous peptide in nature. They are often found in fermentation broths and yeast cultures as well as embedded in larger more complex architectures in a variety of natural products as well as several drugs.[2] In addition, they are often produced as degradation products of polypeptides, especially in processed foods and beverages.[3] They have also been identified in the contents of comets.[4]
- ^ Corey RB (July 1938). "Crystal Structure of Diketopiperazine". Journal of the American Chemical Society. 60 (7): 1598–1604. doi:10.1021/ja01274a023.
- ^ Borthwick AD (May 2012). "2,5-Diketopiperazines: Synthesis, Reactions, Medicinal Chemistry, and Bioactive Natural Products". Chemical Reviews. 112 (7): 3641–3716. doi:10.1021/cr200398y. PMID 22575049.
- ^ Borthwick AD, Da Costa NC (2017). "2,5-Diketopiperazines in Food and Beverages: Taste and Bioactivity". Critical Reviews in Food Science and Nutrition. 57 (4): 718–742. doi:10.1080/10408398.2014.911142. PMID 25629623. S2CID 1334464.
- ^ Shimoyama A, Ogasawara R (April 2002). "Dipeptides and diketopiperazines in the Yamato-791198 and Murchison carbonaceous chondrites". Origins of Life and Evolution of the Biosphere. 32 (2): 165–179. Bibcode:2002OLEB...32..165S. doi:10.1023/A:1016015319112. PMID 12185674. S2CID 21283306.