2,5-Diketopiperazine

2,5-Diketopiperazine
Names
	IUPAC name 2,5-Piperazinedione
	Preferred IUPAC name Piperazine-2,5-dione
	Other names Cyclic dipeptides, cyclo-dipeptides, DKPs, CDPs 2,5 dioxopiperazines (DOPs), dipeptide anhydrides
Identifiers
CAS Number	106-57-0;
3D model (JSmol)	Interactive image;
3DMet	B00497;
Beilstein Reference	112112
ChEBI	CHEBI:16535;
ChEMBL	ChEMBL125229;
ChemSpider	7529;
EC Number	203-411-5;
Gmelin Reference	217756
KEGG	C02777;
PubChem CID	7817;
UNII	240L69DTV7;
	InChI InChI=1S/C4H6N2O2/c7-3-1-5-4(8)2-6-3/h1-2H2,(H,5,8)(H,6,7) Key: BXRNXXXXHLBUKK-UHFFFAOYSA-N;
	SMILES C1C(=NCC(=N1)O)O;
Properties
Chemical formula	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). Infobox references

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. 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. In addition, they are often produced as degradation products of polypeptides, especially in processed foods and beverages. They have also been identified in the contents of comets.

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