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Ansatrienin A (CAS 82189-03-5)

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Alternate Names:
Mycotrienin I
Application:
Ansatrienin A is an ansamycin antibiotic inhibitor of osteoclastic bone resorption
CAS Number:
82189-03-5
Molecular Weight:
636.8
Molecular Formula:
C36H48N2O8
Supplemental Information:
This is as a Dangerous Good for transport and may be subject to additional shipping charges.
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
* Refer to Certificate of Analysis for lot specific data.

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Ansatrienin A, also known as mycotrienin I, with the CAS number 82189-03-5, is a naphthoquinone antibiotic produced by certain strains of the bacterium Streptomyces. This compound is part of the ansamycin class of antibiotics, which are known for their complex macrocyclic structures incorporating a naphthalene ring system. Ansatrienin A acts by inhibiting the enzyme squalene synthase, pivotal in the sterol biosynthesis pathway. This enzyme plays a crucial role in the conversion of farnesyl diphosphate to squalene, an early step in the synthesis of sterols, including key components of cell membranes. By interfering with this process, ansatrienin A disrupts the cellular architecture and metabolic processes reliant on sterols, particularly in fungi and similar organisms. In research, ansatrienin A is used primarily to study cholesterol and sterol biosynthesis pathways. Its unique mechanism offers a tool for dissecting the role of squalene synthase and its products in cellular function and integrity. Additionally, it serves as a model compound in the study of ansamycin antibiotics, aiding in the exploration of their biosynthesis, mode of action, and potential applications in controlling organisms dependent on sterol metabolism. Through these studies, ansatrienin A contributes to a broader understanding of microbial physiology and the potential manipulation of biochemical pathways for research purposes.


Ansatrienin A (CAS 82189-03-5) References

  1. Biosynthesis of ansatrienin (mycotrienin) and naphthomycin. Identification and analysis of two separate biosynthetic gene clusters in Streptomyces collinus Tü 1892.  |  Chen, S., et al. 1999. Eur J Biochem. 261: 98-107. PMID: 10103039
  2. A novel delta(3),delta(2)-enoyl-CoA isomerase involved in the biosynthesis of the cyclohexanecarboxylic acid-derived moiety of the polyketide ansatrienin A.  |  Patton, SM., et al. 2000. Biochemistry. 39: 7595-604. PMID: 10858310
  3. SAR study of a novel triene-ansamycin group compound, quinotrierixin, and related compounds, as inhibitors of ER stress-induced XBP1 activation.  |  Kawamura, T., et al. 2008. J Antibiot (Tokyo). 61: 303-11. PMID: 18653996
  4. Mycotrienin II, a translation inhibitor that prevents ICAM-1 expression induced by pro-inflammatory cytokines.  |  Yamada, Y., et al. 2011. J Antibiot (Tokyo). 64: 361-6. PMID: 21448188
  5. Biosynthesis of the ansamycin antibiotic ansatrienin (mycotrienin) by Streptomyces collinus.  |  Wu, TS., et al. 1987. J Nat Prod. 50: 108-18. PMID: 3598593
  6. Mycotrienin, a new polyene antibiotic isolated from Streptomyces.  |  Coronelli, C., et al. 1967. J Antibiot (Tokyo). 20: 329-33. PMID: 5631366
  7. Potentiation of mitomycin C, 6-mercaptopurine, bleomycin, cis-diamminedichloroplatinum and 5-fluorouracil by mycotrienins and mycotrienols.  |  Kuwano, M., et al. 1983. Gan. 74: 759-66. PMID: 6196249
  8. Studies on mycotrienin antibiotics, a novel class of ansamycins. I. Taxonomy, fermentation, isolation and properties of mycotrienins I and II.  |  Sugita, M., et al. 1982. J Antibiot (Tokyo). 35: 1460-6. PMID: 7161184
  9. Studies on mycotrienin antibiotics, a novel class of ansamycins. II. Structure elucidation and biosynthesis of mycotrienins I and II.  |  Sugita, M., et al. 1982. J Antibiot (Tokyo). 35: 1467-73. PMID: 7161185
  10. Mycotrienins. A new class of potent inhibitors of osteoclastic bone resorption.  |  Feuerbach, D., et al. 1995. J Biol Chem. 270: 25949-55. PMID: 7592784

Ordering Information

Product NameCatalog #UNITPriceQtyFAVORITES

Ansatrienin A, 1 mg

sc-202953
1 mg
$172.00