2,5-diketopiperazine
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IUPAC name
2,5-Piperazinedione
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| Other names
piperazine-2,5-dione
cyclo(Gly-Gly) |
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3D model (JSmol)
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| Properties | |
| C4H6N2O2 | |
| Molar mass | 114.10 g·mol−1 |
| Melting point | 311–312 °C (592–594 °F; 584–585 K) |
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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, also known as piperazine-2,5-dione and as the cyclodipeptide cyclo(Gly-Gly), is an organic compound and the smallest cyclic dipeptide that consists of a six-membered ring containing two amide linkages where the two nitrogen atoms and the two carbonyls are at opposite positions in the ring. It was first synthesized by Curtius and Gloebel in 1888 and was the first compound containing a peptide bond to be studied by X-ray crystallography in 1938. It occurs in cocoa and bread and has a metallic and bitter taste.
2,5-Diketopiperazines (2,5-DKPs) which include mono- and disubstituted 2,5-diketopiperazines, their annulated, spiro-annulated and bridged derivatives are amongst the most ubiquitous peptide derivatives found in nature. They are found in fermentation broths and yeast cultures and this subunit is often found alone or embedded in larger more complex architectures in a variety of natural products isolated from fungi, bacteria, plants, and mammals, and their core structure occurs in several drugs. In addition, they are often produced as degradation products of polypeptides, especially in processed food and beverages, and have been identified in the contents of comets.
There is a widespread occurrence of the 2,5-diketopiperazine core in biologically active natural products. The most structurally diverse 2,5-diketopiperazine natural products are based on tryptophan and proline modified by heterocyclisation and isoprenyl addition. These range from the hepatoxic brevianamide F (cyclo(L-Trp-L-Pro)) to the annulated tremorogenic verruculogen and the spiro-annulated spirotryprostatin B which represent a promising class of antimitotic arrest agents, to the structurally complex (+)-stephacidin A, a bridged 2,5-diketopiperazine that possess a unique bicyclo[2.2.2]diazaoctane core ring system and is active against the human colon HCT-116 cell line.
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