Diketopiperazine

A diketopiperazine (DKP), also known as a dioxopiperazine or piperazinedione, is a class of organic compounds related to

• One isomer is an oxamide obtained from ethylenediamine.
• 2,5-Diketopiperazines are cyclodipeptides often obtainable via condensation of two α-amino acids.
• 2,6-Diketopiperazines may be viewed as cyclized imide derivatives derived from iminodiacetic acids.

Of these three isomeric diketopiperazines, the 2,5-derivatives have attracted the greatest interest.

DKPs are synthesized by a wide range of organisms, including bacteria, fungi, more complex marine microorganisms, and even mammals. However, 90% of gram-negative bacteria synthesize these molecules, making them the target of most studies.^[1]

Biological activity

DKPs have been shown to inhibit the activities of bacteria, fungi, viruses, and potentially protozoa, as well as exhibit antitumor and antiprion properties. The molecule

Despite the great potential for diversity in this class of molecules, natural DPKs containing proline are significantly overrepresented among those known to be biologically active. There also appears to be some bias with regards to stereochemistry, as DD-stereoisomers tend to display stronger antibiotic capabilities.^[1]

References