1222-90-8

Usage

Uses

Used in Pharmaceutical Industry:
Albonoursin is used as an antimalarial agent for its potent in vitro and in vivo activity against malaria. It is a promising candidate for the development of new antimalarial drugs due to its effectiveness in combating the disease.
Used in Antimalarial Drug Development:
Albonoursin is utilized in the research and development of new antimalarial drugs, as it has demonstrated significant potential in treating malaria. Its unique structure and properties make it a valuable compound for further investigation and potential incorporation into novel therapeutic agents.

InChI:InChI=1/C15H16N2O2/c1-10(2)8-12-14(18)17-13(15(19)16-12)9-11-6-4-3-5-7-11/h3-10H,1-2H3,(H,16,19)(H,17,18)/b12-8-,13-9-

Upstream product

• 100-52-7 benzaldehyde 
• 74124-69-9 (3Z,6S)-3-benzylidene-6-isobutylpiperazine-2,5-dione 
• 3354-31-2 (3S,6S)-3-benzyl-6-isobutylpiperazine-2,5-dione 
• 78-84-2 isobutyraldehyde 
• 30166-29-1 1-acetyl-3-[(Z)-benzylidene]-2,5-piperazinedione 

Related news

The albonoursin (cas 1222-90-8) Gene Cluster of S. noursei07/25/2019

Albonoursin [cyclo(ΔPhe-ΔLeu)], an antibacterial peptide produced by Streptomyces noursei, is one of the simplest representatives of the large diketopiperazine (DKP) family. Formation of α,β unsaturations was previously shown to occur on cyclo(L-Phe-L-Leu), catalyzed by the cyclic dipeptide ...detailed

Relevant academic research and scientific papers

Effective production of dehydro cyclic dipeptide albonoursin exhibiting pronuclear fusion inhibitory activity II. Biosynthetic and bioconversion studies

Albornoursin production was greatly enhanced when cycle (r-Leu-L-Phe) (CFL), a tetrahydro derivative of albonoursin, was added to the 2-day culture of an albonoursin-producing actinomycete, Streptomyces albulus KO-23. The increase in albonoursin production paralleled the amount of CFL added. Furthermore, the resting cells of the strain catalyzed the bioconversion of CFL to albonoursin. The optimum pH and temperature for the conversion were found to be pH 10.0 and 50°C. The feeding experiments and the resting-cell reactions revealed that albonoursin is biosynthesized by dehydrogenation of CFL in the actinomycete. This is the first report for a dehydrogenation of amino acid residues at the α,β-positions in cyclic dipeptides.

Biosynthetic intermediates of the tetradehydro cyclic dipeptide albonoursin. Produced by Streptomyces albulus KO-23

The cell-free extract of an albonoursin-producing strain Streptomyces albulus KO-23 catalyzes the conversion of cyclo(L-Leu-L-Phe) (1) to albonoursin (2). At the early stage of this conversion, two compounds were newly formed prior to albonoursin synthesis in the reaction mixture. These compounds were isolated and identified as (Z)-3-benzylidene-6-isobutyl-2,5- piperazinedione (4) and (Z)-3-benzyl-6-isobutylidene-2,5-piperazinedione (3). The cell-free extract also catalyzed the conversion of compound 3 or 4 to albonoursin. From these results, albonoursin was found to be biosynthesized via these compounds from cyclo (L-Leu-L-Phe). These didehydro diketopiperazines exhibited no inhibitory activity toward the first cleavage of sea urchin embryo in contrast to the higher cytotoxicity for albonoursin, indicating that dehydrogenation at α,β-positions of both amino acid residues in diketopiperazines is required for cytotoxicity.

Potassium Fluoride on Alumina: Condensation of 1,4-Diacetylpiperazine-2,5-dione with Aldehydes. Dry Condensation under Microwave Irradiation. Synthesis of Albonursin and Analogues

1,4-Diacetylpiperazine-2,5-dione (1) was condensated with aldehydes (2) with KF on alumina without solvent under microwaves or in at room temperature in the presence of DMF.The reaction was stereoselective and some natural products (4a-c) like albonursin (4c) were synthesized.