Albonoursin

Albonoursin

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Albonoursin
Category Antibiotics
Catalog number BBF-00410
CAS 1222-90-8
Molecular Weight 256.30
Molecular Formula C15H16N2O2
Purity 99%

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Description

It is produced by the strain of Streptomyces noursei and Str. albus var fungatus. It has the activity of anti-gram-positive bacteria and some gram-negative bacteria.

Specification

Synonyms Albonoursine; Albonursin; cyclo(DeltaPhe-DeltaLeu); 3-Benzylidene-6-isobutylidene-2,5-dioxopiperazine; cyclo(dehydroleucyl-dehydrophenylalanyl); CHEBI:71609; 2,5-Piperazinedione, 3-(2-methylpropylidene)-6-(phenylmethylene)-, (Z,Z)-
Storage 2-8 °C
IUPAC Name (3Z,6Z)-3-benzylidene-6-(2-methylpropylidene)piperazine-2,5-dione
Canonical SMILES CC(C)C=C1C(=O)NC(=CC2=CC=CC=C2)C(=O)N1
InChI InChI=1S/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-
InChI Key LCIIOYPBHIZBOD-JMVBYTIWSA-N

Properties

Appearance Colorless Flake Crystals
Antibiotic Activity Spectrum Gram-positive bacteria; Gram-negative bacteria
Boiling Point 567.8 °C at 760 mmHg
Melting Point 275-276 °C
Density 1.221 g/cm3

Reference Reading

1. Two New Piperazine-Triones from a Marine-Derived Streptomycetes sp. Strain SMS636
Xiuli Xu, Jiahui Han, Rui Lin, Steven W Polyak, Fuhang Song Mar Drugs. 2019 Mar 21;17(3):186. doi: 10.3390/md17030186.
Two new piperazine-triones lansai E and F (1, 2), together with four known secondary metabolites lansai D (3), 1-N-methyl-(E,Z)-albonoursin (4), imidazo[4,5-e]-1,2,4-triazine (5), and streptonigrin (6) were isolated from a deep-sea-derived Streptomycetes sp. strain SMS636. The structures of the isolated compounds were confirmed by comprehensive spectroscopic analysis, including HRESIMS, 1D and 2D NMR. Compound 4 exhibited moderate antibacterial activities against Staphylococcus aureus and methicillin resistant S. aureus (MRSA) with Minimum Inhibitory Concentration (MIC) values of 12.5 and 25 μg/mL, respectively. Compound 6 displayed significant antibacterial activities against S. aureus, MRSA and Bacillus Calmette-Guérin (BCG) with MIC values of 0.78, 0.78 and 1.25 μg/mL, respectively.
2. Analysis of the biosynthesis of antibacterial cyclic dipeptides in Nocardiopsis alba
Yongli Li, Ying-Mi Lai, Yi Lu, Yu-Liang Yang, Shawn Chen Arch Microbiol. 2014 Nov;196(11):765-74. doi: 10.1007/s00203-014-1015-x. Epub 2014 Jul 22.
Nocardiopsis alba is frequently isolated from environment and has recently been suggested as a casual symbiotic actinobacterium of diverse invertebrates. Using activity-guided fractionation, we purified two antibacterial cyclic dipeptides, cyclo(ΔPhe-ΔLeu) (albonoursin) and cyclo(ΔmTyr-ΔLeu), from a culture of Nocardiopsis alba ATCC BAA-2165. Analysis of N. alba genome revealed genetic information similar to albonoursin biosynthetic gene cluster, albABC. An albABC gene deletion mutant of N. alba was generated. Liquid chromatography-mass spectrometry analysis showed that the mutant could not produce the cyclic dipeptides. Cyclic dipeptide production in the mutant was restored by genetic complementation with the albABC cloned in a native plasmid of Nocardiopsis. β-Glucuronidase reporter assays with a second mutant construct, in which albABC promoter is transcriptionally fused to the reporting gene gusA, indicated that albABC gene expression was subject to osmoregulation. The system presented will be used to study the metabolic and genetic control of cyclic dipeptide biosynthesis in Nocardiopsis.
3. Cyclodipeptide synthases are a family of tRNA-dependent peptide bond-forming enzymes
Muriel Gondry, Ludovic Sauguet, Pascal Belin, Robert Thai, Rachel Amouroux, Carine Tellier, Karine Tuphile, Mickaël Jacquet, Sandrine Braud, Marie Courçon, Cédric Masson, Steven Dubois, Sylvie Lautru, Alain Lecoq, Shin-ichi Hashimoto, Roger Genet, Jean-Luc Pernodet Nat Chem Biol. 2009 Jun;5(6):414-20. doi: 10.1038/nchembio.175.
Cyclodipeptides and their derivatives belong to the diketopiperazine (DKP) family, which is comprised of a broad array of natural products that exhibit useful biological properties. In the few known DKP biosynthetic pathways, nonribosomal peptide synthetases (NRPSs) are involved in the synthesis of cyclodipeptides that constitute the DKP scaffold, except in the albonoursin (1) pathway. Albonoursin, or cyclo(alpha,beta-dehydroPhe-alpha,beta-dehydroLeu), is an antibacterial DKP produced by Streptomyces noursei. In this pathway, the formation of the cyclo(Phe-Leu) (2) intermediate is catalyzed by AlbC, a small protein unrelated to NRPSs. We demonstrated that AlbC uses aminoacyl-tRNAs as substrates to catalyze the formation of the DKP peptide bonds. Moreover, several other bacterial proteins, presenting moderate similarity to AlbC, also use aminoacyl-tRNAs to synthesize various cyclodipeptides. Therefore, AlbC and these related proteins belong to a newly defined family of enzymes that we have named cyclodipeptide synthases (CDPSs).

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Tip: Chemical formula is case sensitive. C22H30N4O c22h30n40
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