A macrolide antibiotic
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Oleandomycin

Item No. 16552

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(3R,5R,6S,7R,8R,11R,12S,13R,14S,15S)-14-(((2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-6-hydroxy-12-(((2R,4S,5S,6S)-5-hydroxy-4-methoxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-5,7,8,11,13,15-hexamethyl-1,9-dioxaspiro[2.13]hexadecane-4,10-dione
CAS Number
3922-90-5
Molecular Formula
C35H61NO12
Formula Weight
687.9
Purity
≥95%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: SolubleDMSO: SolubleEthanol: SolubleMethanol: Soluble
SMILES
O=C1[C@@H]([C@H]([C@H]([C@H](OC([C@@H]([C@H]([C@@H]([C@H]([C@H](C[C@@]12CO2)C)O[C@]3([C@@H]([C@H](C[C@H](O3)C)N(C)C)O)[H])C)O[C@@]4(O[C@H]([C@@H]([C@H](C4)OC)O)C)[H])C)=O)C)C)O)C
InChi Code
InChI=1S/C35H61NO12/c1-16-14-35(15-43-35)32(40)19(4)27(37)18(3)22(7)46-33(41)21(6)31(47-26-13-25(42-11)28(38)23(8)45-26)20(5)30(16)48-34-29(39)24(36(9)10)12-17(2)44-34/h16-31,34,37-39H,12-15H2,1-11H3/t16-,17+,18-,19+,20+,21+,22+,23-,24-,25-,26-,27-,2
InChi Key
RZPAKFUAFGMUPI-QESOVKLGSA-N
Origin
Bacterium/Streptomyces sp.
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

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    Product Description

    Oleandomycin is a classic macrolide antibiotic produced by strains of Streptomyces that demonstrates antimicrobial activity similar to penicillin and erythromycin.1 Structurally, it consists of a macrocyclic lactone ring of 14 carbon atoms with one sugar, oleandrose, and one amino sugar, desoxamine, attached to the lactone ring. The mechanism of its biosynthesis and development of resistance to its antibiotic activity have been studied in order to understand the reactive enzymes in these processes.1,2

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Vilches, C., Méndez, C., Hardisson, C., et al. Biosynthesis of oleandomycin by Streptomyces antibioticus: Influence of nutritional conditions and development of resistance. J. Gen. Microbiol. 136(8), 1447-1454 (1990).

    2. Quirós, L.M., and Salas, J.A. Biosynthesis of the macrolide oleandomycin by Streptomyces antibioticus. Purification and kinetic characterization of an oleandomycin glucosyltransferase. The Journal of Biological Chemisty 270(31), 18234-18239 (1995).