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BioViotica
Terreic acid
65
CHF
CHF 65.00
In stock
BVT-0477-M0011 mgCHF 65.00
BVT-0477-M0055 mgCHF 215.00
| Product Details | |
|---|---|
| Synonyms | TA; (1R,6S)-3-hydroxy-4-methyl-7-oxabicyclo[4.1.0]hept- 3-ene-2,5-dione; (-)-Terreic acid |
| Product Type | Chemical |
| Properties | |
| Formula |
C7H6O4 |
| MW | 154.1 |
| CAS | 121-40-4 |
| RTECS | RN8925000 |
| Source/Host Chemicals | Isolated from Aspergillus terreus. |
| Purity Chemicals | ≥99% (HPLC) |
| Appearance | White to off-white solid. |
| Solubility | Soluble in DMSO (10mg/ml), EtOH, MeOH, acetone, DCM or water (1mg/ml, warming and sonication might be necessary). |
| Identity | Determined by 1H-NMR. |
| InChi Key | ATFNSNUJZOYXFC-RQJHMYQMSA-N |
| Smiles | O=C([C@@H]1[C@H]2O1)C(C)=C(O)C2=O |
| Shipping and Handling | |
| Shipping | AMBIENT |
| Short Term Storage | +4°C |
| Long Term Storage | -20°C |
| Handling Advice | Protect from light. |
| Use/Stability |
Stable for at least 1 year after receipt when stored at -20°C. Store solutions at -20°C in the dark. |
| Documents | |
| MSDS |
 Download PDF |
| Product Specification Sheet | |
| Datasheet |
Download PDF |
Description
- Mycotoxin.
- Antibacterial and anticancer agent.
- A cell-permeable quinone epoxide antibiotic. Covalent inhibitor of the bacterial enzyme UDP-N-acetylglucosamine 1-carboxyvinyltransferase (MurA), which catalyzes the first committed step of bacterial cell wall biosynthesis. More potent than the known MurA inhibitor Fosphomycin.
- Reversible, substrate competitive and selective inhibitor of Bruton's tyrosine kinase (BTK) catalytic activity, an important factor in B-cell and mast cell activation. Shown to bind to the BTK pleckstrin homology domain (BTK-PH) and block the interaction between the BTK-PH and PKC, affecting the catalytic activity of BTK but not of PKC. Has minimal effect on Lyn, Syk, PKA, casein kinase I, ERK1, ERK2, and p38 kinase activities.
- Antioxidant.
Product References
- Structure of terreic acid: J.C. Sheehan, et al.; JACS 80, 5536 (1958)
- Studies on terreic acid: H. Yamamoto, et al.; J. Antibiot. 33, 320 (1980)
- In vivo and in vitro studies on the binding nature of terreic acid with macromolecules such as protein and nucleic acids: T. Subramanian, et al.; Toxicol. Lett. 10, 249 (1982)
- Terreic acid - a diabetogenic mycotoxin in rats: E.R.B. Shanmugasundaram, et al.; Curr. Sci. 53, 1290 (1984)
- Terreic acid, a quinone epoxide inhibitor of Bruton's tyrosine kinase: Y. Kawakami, et al.; PNAS 96, 2227 (1999)
- Regulation of protein kinase CβI by two protein-tyrosine kinases, Btk and Syk: Y. Kawakami, et al.; PNAS 97, 7423 (2000)
- Modulation of the Fcepsilon receptor I signaling by tyrosine kinase inhibitors: search for therapeutic targets of inflammatory and allergy diseases: P. Luskova & P. Draber; Curr. Pharm. Des. 10, 1727 (2004)
- The Fungal Product Terreic Acid Is a Covalent Inhibitor of the Bacterial Cell Wall Biosynthetic Enzyme UDP-N-Acetylglucosamine 1-Carboxyvinyltransferase (MurA): H. Han, et al.; Biochemistry 49, 4276 (2010)
- Isolation of antioxidant compounds from Aspergillus terreus LS01: R.T. Dewi, et al.; J. Microb. Biochem. Techno. 4, 10 (2012)
- Differential antibacterial properties of the MurA inhibitors terreic acid and fosfomycin: S. Olesen, et al.; J. Basic Microbiol. 54, 322 (2014)
- Molecular Genetic Characterization of Terreic Acid Pathway in Aspergillus terreus: C.-J. Guo, et al.; Org. Lett. 16, 5250 (2014)
- Escherichia coli N-acetylglucosamine-1-phosphate-uridyltransferase/ glucosamine-1-phosphateacetyltransferase (GlmU) inhibitory activity of terreic acid isolated from Aspergillus terreus: R. Sharma, et al.; J. Biomol. Screen. 21, 342 (2016)
- Heterologous pathway assembly reveals molecular steps of fungal terreic acid biosynthesis: C. Kong, et al.; Sci. Rep. 8, 1 (2018)
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