Aureusimine B
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| Category | Enzyme inhibitors |
| Catalog number | BBF-04198 |
| CAS | 170713-71-0 |
| Molecular Weight | 228.29 |
| Molecular Formula | C14H16N2O |
| Purity | >95% by HPLC |
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Description
It is an inhibitor of the protease Calpain produced by the strain of Streptomyces sp. SC433. It is a small molecular weight monoketopiperazine formed non-ribosomally by the fusion of phenylalanine and valin.
Specification
| Synonyms | Phevalin; 3-(1-Methylethyl)-6-(phenylmethyl)-2(1H)-pyrazinone; 6-Benzyl-3-isopropylpyrazin-2-one |
| Storage | Store at 2-8°C |
| IUPAC Name | 6-benzyl-3-propan-2-yl-1H-pyrazin-2-one |
| Canonical SMILES | CC(C)C1=NC=C(NC1=O)CC2=CC=CC=C2 |
| InChI | InChI=1S/C14H16N2O/c1-10(2)13-14(17)16-12(9-15-13)8-11-6-4-3-5-7-11/h3-7,9-10H,8H2,1-2H3,(H,16,17) |
| InChI Key | CZUORGWXUVRUMV-UHFFFAOYSA-N |
| Source | Synthetic |
Properties
| Appearance | Pale Beige to Pale Brown Solid |
| Melting Point | 117-118°C |
| Density | 1.10±0.1 g/cm3 (Predicted) |
| Solubility | Soluble in Ethanol, Methanol, Ethyl Acetate; Poorly soluble in Water |
Reference Reading
1. Optimizing dimodular nonribosomal peptide synthetases and natural dipeptides in an Escherichia coli heterologous host
Nathan A Magarvey, Morgan A Wyatt Biochem Cell Biol . 2013 Aug;91(4):203-8. doi: 10.1139/bcb-2012-0097.
Nonribosomal peptides are an important class of natural products that have a broad range of biological activities. Their structural complexity often prevents simple chemical synthesis, and production from the natural producer is often low, which deters pharmaceutical development. Expression of biosynthetic machinery in heterologous host organisms like Escherichia coli is one way to access these structures, and subsequent optimization of these systems is critical for future development. We utilized the aureusimine biosynthetic gene cluster as a model system to identify the optimal conditions to produce nonribosomal peptides in the isopropyl β-d-1-thiogalactopyranoside (IPTG)-inducible T7 promoter system of pET28. Single reaction monitoring of nonribosomal products was used to find the optimal concentration of IPTG, postinduction temperature, and the effect of amino acid precursor supplementation. In addition, principle component analysis of these extracts identified 3 previously undiscovered pyrazine products of the aureusimine biosynthetic locus, highlighting the utility of heterologously expressing nonribosomal peptide synthetases to find new products.
2. Phileucin - A Cyclic Dipeptide Similar to Phevalin (Aureusimine B) from Streptomyces coelicolor M1146
Michael Gütschow, Nils Böhringer, Till F Schäberle, Gabriele M König Nat Prod Commun . 2017 Jan;12(1):107-109.
Overexpression of a putative type III polyketide synthase (PKSIII) from the marine myxobacterium Enhygromyxa salina SWB007 in Streptoinyces coelicolor MI 146 led to the accumulation of a novel monoketopiperazine consisting of phenylalanine and isoleucine. This compound was named phileucin and shows high structural similarity to phevalin (aureusimine B). The protease inhibiting activity was tested against human cathepsin L, human leukocyte elastase; bovine trypsin and bovine chymotrypsin. In contrast to phevalin, no protease inhibition was observed.
3. Targeted and untargeted analysis of secondary metabolites to monitor growth and quorum sensing inhibition for methicillin-resistant Staphylococcus aureus (MRSA)
Derick D Jones Jr, Daniel A Todd, William J Crandall, Nadja B Cech, Christian Jenul, Lindsay K Caesar, Chantal V Pelzer, Alexander R Horswill J Microbiol Methods . 2020 Sep;176:106000. doi: 10.1016/j.mimet.2020.106000.
Drug resistant infections are an increasing problem world-wide, responsible for an estimated 700,000 annual mortalities. The use of antibiotics to treat such infections has resulted in the development of resistant bacterial pathogens such as methicillin-resistant Staphylococcus aureus (MRSA). One potential alternative strategy for treating drug resistant bacterial infections is to inhibit the production of toxins, thereby making the bacteria less harmful to the host, a so called "anti-virulence" approach. In MRSA, the agr quorum sensing system is one of the major regulators of toxin production, and quorum sensing inhibitors that target this system are a promising anti-virulence strategy. With this study, we developed a method that enables the activity of quorum sensing inhibitors to be measured using ultra-performance liquid chromatography coupled to mass spectrometry (UPLC-MS). This method is an improvement over existing methods because it can be employed to distinguish antimicrobial activity from quorum sensing inhibition activity based on the UPLC-MS data. This is possible by simultaneously tracking production of metabolites regulated by the agr quorum sensing system (AIP-I and formylated δ-toxin) and a metabolite that appears not to be agr regulated under the conditions of this study (aureusimine B). The newly developed method provides more nuanced indication of how metabolite production changes over time and in response to quorum sensing or growth inhibition than is possible with commonly employed spectroscopic methods.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
