The diketopiperazines: 2,3-, 2,5, and 2,6-isomers.
A diketopiperazine (DKP), also known as a dioxopiperazine or piperazinedione, is a class of organic compounds related to piperazine but containing two amide linkages. DKP's are the smallest known class of cyclic peptide.[1] Despite their name, they are not ketones, but amides. Three regioisomers are possible, differing in the locations of the carbonyl groups.
Retosiban[2] is a diketopiperazine being investigated as an oral drug.
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.[3][4] Due to their appearance in biologically active natural products, medicinal chemists have been inspired to use DKPs to circumvent the poor physical and metabolic properties of peptides in the course of drug discovery.
^Carvalho, M. P. de; Abraham, W.-R. (2012). "Antimicrobial and Biofilm Inhibiting Diketopiperazines". Current Medicinal Chemistry. 19 (21): 3564–3577. doi:10.2174/092986712801323243. hdl:10033/243651. PMID 22709011.
^Borthwick AD, Liddle J (January 2013). "Retosiban and Epelsiban: Potent and Selective Orally available Oxytocin Antagonists". In Domling A (ed.). Methods and Principles in Medicinal Chemistry: Protein-Protein Interactions in Drug Discovery. Weinheim: Wiley-VCH. pp. 225–256. ISBN 978-3-527-33107-9.
^Borthwick, A. D. (2012). "2,5-Diketopiperazines: Synthesis, Reactions, Medicinal Chemistry, and Bioactive Natural Products". Chem. Rev. 112 (7): 3641–716. doi:10.1021/cr200398y. PMID 22575049.
^Witiak DT, Wei Y. (1990). "Dioxopiperazines: chemistry and biology". Progress in Drug Research. 35: 249–363. doi:10.1007/978-3-0348-7133-4_7. ISBN 3-7643-2499-6. PMID 2290982.
A diketopiperazine (DKP), also known as a dioxopiperazine or piperazinedione, is a class of organic compounds related to piperazine but containing two...
body of inhibiting PDE11 are not known. Tadalafil is an annulated 2,5-diketopiperazine. It is also a 1,2,3,4-tetrahydro-β-carboline. Tadalafil can be synthesized...
2CONHCH 2COO− + H2O Pyrolysis of glycine or glycylglycine gives 2,5-diketopiperazine, the cyclic diamide. It forms esters with alcohols. They are often...
Partisi, Revolutionary Communard Party, Turkey Diketopiperazine, a class of organic compounds 2,5-Diketopiperazine, a specific form Duffin–Kemmer–Petiau algebra...
coffee. The bitter flavor of diketopiperazines is perceptible at around 20 mg/liter of water. The content of diketopiperazines in espresso is about 20 to...
tending to polymerize when stored at room temperature or convert to diketopiperazine. The hydrochloride is shelf-stable. "Glycine methyl ester hydrochloride"...
Dipeptides activate G-cells found in the stomach to secrete gastrin. Diketopiperazines are a special class of dipeptides, which are cyclic. They form as...
of aspergillus that belongs to a class of naturally occurring 2,5-diketopiperazines. It is an annulated analogue of cyclo(L-Trp-L-Pro) which belongs to...
synthesized by Emil Fischer and Ernest Fourneau in 1901 by boiling 2,5-diketopiperazine (glycine anhydride) with hydrochloric acid. Shaking with alkali and...
Penicillium which occurs in kangaroo rats and produces penicillin and the diketopiperazine dipodazine. List of Penicillium species MycoBank UniProt Henk, D. A...
(DMT G) belongs to the family of drimentines, which are terpenylated diketopiperazines. As the name suggests, DMT G contains two different parts, one comes...
stored at a relatively high temperature can lead to the formation of diketopiperazine, a cyclo (Pro-Leu) that makes it bitter as it ages Sake has high microbiological...
related compounds. Enzymatic epoxidation of phenylalanine-derived diketopiperazine forms the arene oxide, which undergoes a 6π disrotatory ring opening...
sulfur-containing mycotoxin that belongs to a class of naturally occurring 2,5-diketopiperazines produced by several species of fungi, especially those of marine origin...
and Penicillium, that belong to a class of naturally occurring 2,5-diketopiperazines. Biosynthesis pathway of fumitremorgin pathway involves several different...
2014). "Lysobacter capsici AZ78 produces cyclo(L-Pro-L-Tyr), a 2,5-diketopiperazine with toxic activity against sporangia of Phytophthora infestans and...
cyclo-(L-Trp-L-Pro), belongs to a class of naturally occurring 2,5-diketopiperazines. It is the simplest member and the biosynthetic precursor of a large...
structures of proteins were proposed by various researchers, such as the diketopiperazine model of Emil Abderhalden and the pyrrol/piperidine model of Troensegaard...
aizumenses in 1972. It belongs to a class of naturally occurring 2,5-diketopiperazines, that are among the most numerous of all the naturally occurring peptide...
piscarium Westling that belong to a class of naturally occurring 2,5-diketopiperazines. The cytotoxic dehydroproline tryptophan derivatives piscarinines...
is a mycotoxin that belongs to a class of naturally occurring 2,5-diketopiperazines produced by various fungi, particularly species from the genus Penicillium...
acid Dihydrouracil, an intermediate in the catabolism of uracil 2,5-Diketopiperazine Ethyl diazoacetate, a reagent used in organic chemistry Muscimol, the...
to the alpha amine of another). The smallest such species are 2,5-diketopiperazines, being derived from the cyclisation of a dipeptide. Cyclic isopeptides...
Piperacillin is a broad-spectrum β-lactam antibiotic of the ureidopenicillin class. The chemical structure of piperacillin and other ureidopenicillins...
did not allow for the incorporation of functionality on the interior diketopiperazine (DKP) nitrogens. Much work has been done to allow for the functionalization...
reducing sugars like fructose. Unlike aspartame, neotame doesn't form diketopiperazines via intra-molecular cyclization due to its N-alkyl substitution with...
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