Pimaricin, Streptomyces chattanoogensis An antifungal polyene macrolide

Pimaricin, Streptomyces chattanoogensis (CAS 7681-93-8)

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Synonym: Natamycin
Application: An antifungal polyene macrolide
CAS Number: 7681-93-8
Purity: >98%
Molecular Weight: 665.7
Molecular Formula: C33H47NO13
* Refer to Certificate of Analysis for lot specific data (including water content).
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Pimaricin, Streptomyces chattanoogensis is an antifungal macrolide polyene that binds to cell membrane sterols. Investigations show that the compound predominantly binds to the main sterol in fungal and yeast membranes, ergosterol. Ergosterol is a building block of yeasts and molds, which is responsible for intracellular nutrient transport, and therefore vital for their survival. As ergosterol is not present in the outer membranes of bacteria, these remain unaffected.
Pimarcin has been used as a fungicide in agar media and CYP (cytochrome P450) PimD research proposes that the epoxidiation of Pimaricin occurs through a hydroperoxoferric compound. Pimarcin studies reveal that the regulator PimM binds to eight promoters of Pimarcin genes and its biosynthesis is influenced by a cholesterol oxidase protein encoded by PimE.


References

1. Weisblum, B. 1984. Br. Med. Bull. 40: 47-53. PMID: 6442874
2. Pedersen, J.C. 1992. Appl. Environ. Microbiol. 58: 1064-1066. PMID: 16348667
3. Mendes, M.V., et al. 2007. Chem. Biol. 14: 279-290. PMID: 17379143
4. Kells, P.M., et al. 2010. Chem. Biol. 17: 841-851. PMID: 20797613
5. Santos-Aberturas, J., et al. 2010. J Biol Chem. [Epub ahead of print]. PMID: 21187288

Appearance :
Powder
Physical State :
Solid
Solubility :
Soluble in Acetic acid (5 mg/ml), 0.1%HCOOH in Methanol (1 mg/ml), water (<1 mg/ml), ethanol (<1 mg/ml), DMSO (7 mg/ml), and methanol (~1 mg/ml).
Storage :
Store at 4° C
Melting Point :
280° C
Boiling Point :
952.17° C at 760 mmHg (Predicted)
Density :
1.39 g/cm3 (Predicted)
Refractive Index :
n20D 1.62 (Predicted)
Optical Activity :
α20/D +265.8°, c = 0.6 in Acetic Acid
pK Values :
pKa: 3.71 (Predicted), pKb: 8.12 (Predicted)
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
WGK Germany :
3
RTECS :
TK3325000
PubChem CID :
6473973
Merck Index :
14: 6427
MDL Number :
MFCD00135085
EC Number :
231-683-5
SMILES :
C[C@@H]1O[C@@H](O[C@@H]2C[C@@H]3O[C@@](O)(C[C@H](O)[C@H]3C(O)=O)C[C@@H](O)C[C@H]3O[C@@H]3\C=C\C(=O)O[C@H](C)C\C=C\C=C\C=C\C=C\2)C(O)C(N)[C@@H]1O

Download SDS (MSDS)

Certificate of Analysis

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