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.^[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.

[1] Corey RB (July 1938). "Crystal Structure of Diketopiperazine". Journal of the American Chemical Society. 60 (7): 1598–1604. doi:10.1021/ja01274a023.

[pmid22575049-2] 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.

[pmid25629623-3] 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.

[pmid12185674-4] 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.

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