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Aureothin

BVT-0303-M001 1 mg $220.00
BVT-0303-M005 5 mg $660.00
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Additional Information

Product Data
Synonyms Mycolutein; Distacin; JA 2814K; Antibiotic 74A; BRN 0058476
Properties
Formula C22H23NO6
MW 397.4
Merck Index 10:879
CAS 2825-00-5
RTECS UQ0800000
Source/Host Chemicals Isolated from Streptomyces thioluteus.
Purity ≥96% (HPLC)
Appearance Yellow to light olive solid.
Solubility Soluble in 100% ethanol, methanol, DMSO, dimethylformamide, dicholormethane or acetone.
Identity Determined by 1H-NMR and UV.
Origin Manufactured by BioViotica.
InChi Key GQKXCBCSVYJUMI-RCGCBBHSSA-N
Product Type Chemical
Shipping and Handling
Shipping AMBIENT
Short Term Storage +4°C
Long Term Storage -20°C
Handling Advice Protect from light when in solution.
Use/Stability Stable for at least 1 year after receipt when stored at -20°C. After reconstitution protect from light at -20°C.
Documents
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Product Description

  • Oxidoreductase inhibitor.
  • Antitrypanosomal, antibacterial, antifungal, insecticidal and pesticidal.
  • Antitumor compound.

Product References

  1. The structure of aureothin, a nitro compound obtained from Streptomyces thioluteus: Y. Hirata, et al.; Tetrahedron 14, 252 (1961)
  2. Identification of mycolutein and pulvomycin as aureothin and labilomycin respectively: J.L. Schwartz, et al.; J. Antibiot. 29, 236 (1976)
  3. Two binding sites of inhibitors in NADH: ubiquinone oxidoreductase (complex I). Relationship of one site with the ubiquinone-binding site of bacterial glucose:ubiquinone oxidoreductase: T. Friedrich, et al.; Eur. J. Biochem. 219, 691 (1994)
  4. Absolute configuration of (+)-aureothin: A toxic Metabolite posessing gamma-pyrone unit: Y. Ishibashi, et al.; Bull. Chem. Soc. Jpn. 68, 3643 (1995)
  5. Gamma-pyrone compounds with selective and potent anti-Helicobacter pylori activity: M. Taniguchi, et al.; J. Antibiot. 53, 844 (2000)
  6. Dissection of the late steps in aureothin biosynthesis: M. Müller, et al.; ChemBioChem 7, 37 (2006)
  7. New aureothin derivative, alloaureothin, from Streptomyces sp. MM23: J.Y. Ueda, et al.; J. Antibiot. 60, 321 (2007)
  8. Chemoenzymatic total synthesis of the antiproliferative polyketide (+)-(R)-aureothin: M. Werneburg & C. Hertweck; Chembiochem 9, 2064 (2008)
  9. Selective and potent in vitro antitrypanosomal activities of ten microbial metabolites: K. Otoguro, et al.; J. Antibiot. 61, 372 (2008)
  10. Natural lipophilic inhibitors of mitochondrial complex I are candidate toxins for sporadic neurodegenerative tau pathologies: M. Höllerhagen, et al.; Exp. Neurol. 220, 133 (2009)
  11. Evolution of metabolic diversity in polyketide-derived pyrones: using the non-colinear Aureothin assembly line as a model system: B. Busch, et al.; Phytochemistry 70, 1833 (2009)
  12. Exploiting enzymatic promiscuity to engineer a focused library of highly selective antifungal and antiproliferative Aureothin analogues: M. Werneburg, et al.; J. Am. Chem. Soc. 132, 10407 (2010)
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