A polyketide antibiotic
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Aurodox

Item No. 27584

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(αS,2R,3R,4R,6S)-N-[(2E,4E,6S,7R)-7-[(2S,3S,4R,5R)-5-[(1E,3E,5E)-7-(1,2-dihydro-4-hydroxy-1-methyl-2-oxo-3-pyridinyl)-6-methyl-7-oxo-1,3,5-heptatrien-1-yl]tetrahydro-3,4-dihydroxy-2-furanyl]-6-methoxy-5-methyl-2,4-octadien-1-yl]-α-ethyltetrahydro-2,3,4-trihydroxy-5,5-dimethyl-6-(1E,3Z)-1,3-pentadien-1-yl-2H-pyran-2-acetamide
CAS Number
12704-90-4
Synonyms
  • Antibiotic X 5108
  • Goldinodox
  • Goldinomycin
  • 1-methyl-Mocimycin
Molecular Formula
C44H62N2O12
Formula Weight
811.0
Purity
≥85% (mixture of tautomers)
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMSO: SolubleEthanol: 1 mg/mlMethanol: Slightly soluble: 0.1-1 mg/mLMethanol: Soluble
SMILES
O[C@H]1[C@@H](/C=C/C=C/C=C(C)/C(C2=C(O)C=CN(C)C2=O)=O)O[C@]([C@H](C)[C@@H](/C(C)=C/C=C/CNC([C@@H](CC)[C@]3(O)[C@H](O)[C@H](O)C(C)(C)[C@H](/C=C/C=C\C)O3)=O)OC)([H])[C@H]1O
InChi Code
InChI=1S/C44H62N2O12/c1-10-12-14-22-32-43(6,7)39(51)40(52)44(55,58-32)29(11-2)41(53)45-24-18-17-20-27(4)37(56-9)28(5)38-36(50)35(49)31(57-38)21-16-13-15-19-26(3)34(48)33-30(47)23-25-46(8)42(33)54/h10,12-23,25,28-29,31-32,35-40,47,49-52,55H,11,24H2,1-9H3,(H,45,53)/b12-10-,15-13+,18-17+,21-16+,22-14+,26-19+,27-20+/t28-,29-,31-,32+,35+,36+,37-,38+,39+,40-,44-/m1/s1
InChi Key
NTAHMPNXQOYXSX-WKSONYIQSA-N
Origin
Bacterium/Streptomyces sp.
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Product Description

    Aurodox is a polyketide antibiotic originally isolated from S. goldiniensis.1 It is active against Gram-positive bacteria, including B. megaterium, B. anthracis, and M. hominis (MICs = 0.06, 0.6, and 3-10 µg/ml, respectively), as well as Pneumococcus and Streptomyces species (MICs = 3-12 and 3-30 µg/ml, respectively). It is effective against S. pyogenes infection in mice with a 50% curative dose (CD50) value of 71 mg/kg. Aurodox inhibits bacterial protein synthesis by binding to bacterial elongation factor Tu (EF-Tu) and inhibiting its release from the ribosome.2,3

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Berger, J., Lehr, H.A., Teitel, S., et al. A new antibiotic X-5108 OF Streptomyces origin. I. Production, isolation and properties. J. Antibiot. (Tokyo) 26(1), 15-22 (1973).

    2. Wolf, H., Chinali, G., and Parmeggiani, A. Mechanism of the inhibition of protein synthesis by kirromycin. Role of elongation factor Tu and ribosomes. Eur. J. Biochem. 75(1), 67-75 (1977).

    3. Bhuta, P., and Chládek, S. Stimulation of Escherichia coli elongation factor Tu-dependent GTP hydrolysis by aminoacyl oligonucleotides in the presence of aurodox. FEBS Lett. 122(1), 113-116 (1980).