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Aurodox

Antibiotic
 
ALX-380-314-MM25 2.5 mg Inquire for pricing
 
ALX-380-314-M001 1 mg Inquire for pricing
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Inhibits bacterial protein biosynthesis by interrupting the functional cycle of Elongation Factor-Tu (EF-Tu). Weakly acidic. pKa = 6.1.

Product Specification

Alternative Name:1-Methylmocimycin, X 5108, Goldinodox, (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
 
Formula:C44H62N2O12
 
MW:811.0
 
Source:Isolated from Streptomyces sp. K06-0806.
 
CAS:12704-90-4
 
Purity:≥95% (HPLC)
 
Appearance:Yellow solid.
 
Solubility:Soluble in acetone, chloroform, ethyl acetate, methanol or methylene chloride; insoluble in water.
 
Shipping:Ambient
 
Long Term Storage:-20°C
 
Use/Stability:Unstable in acidic or basic solutions. Can be kept in aqueous solutions at pH 7-9 for approx. 4h at 25°C without significant loss of activity.
 
Handling:Protect from light.
 
Scientific Background:Aurodox is the N-methyl derivative of kirromycin. Aurodox has been shown to interfere with the role of bacterial elongation factor Tu (EF-Tu) in protein biosynthesis: Like kirromycin, aurodox interrupts the functional cycle of EF-Tu by inhibiting the release of the EF-Tu·GDP complex from the ribosome, thus provoking stalled ribosomes that cause a polysomal traffic jam on the mRNA. The crystal structure of the complex between EF-Tu.GDP and aurodox has been elucidated and provided substantial insights into the molecular mechanisms underlying the antibotic activity of aurodox.
 
Technical Info/Product Notes:Manufactured with courtesy strain from The Kitasato Institute.
 
alx-380-314
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Product Literature References

Conformational change of elongation factor Tu (EF-Tu) induced by antibiotic binding. Crystal structure of the complex between EF-Tu.GDP and aurodox: L. Vogeley, et al.; J. Biol. Chem. 276, 17149 (2001), Abstract; Full Text
Effects of nucleotide- and aurodox-induced changes in elongation factor Tu conformation upon its interactions with aminoacyl transfer RNA. A fluorescence study: V.A. Dell, et al.; Biochemistry 29, 1757 (1990), Abstract;
Synthetic analogs of aurodox and kirromycin active on elongation factor Tu from Escherichia coli: G. Chinali; J. Antibiot. 34, 1039 (1981), Abstract;
Stimulation of Escherichia coli elongation factor Tu-dependent GTP hydrolysis by aminoacyl oligonucleotides in the presence of aurodox: P. Bhuta & S. Chladek; FEBS Lett. 122, 113 (1980), Abstract;
Increased production of the antibiotic aurodox (X-5108) by aurodox-resistant mutants: J. Unowsky & D.C. Hoppe; J. Antibiot. 31, 662 (1978), Abstract;
Feedback inhibition of the synthesis of an antibiotic: aurodox (X-5108): C. Liu, et al.; J. Antibiot. 30, 244 (1977), Abstract;

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