Oleandomycin

• CAT Number: R052467
• CAS Number: 3922-90-5
• Molecular Formula: C35H61NO12
• Molecular Weight: 687.9
• Purity: ≥95%
• Synonyms: 8-(3,5-Dihydroxy-2,4-dimethylhexanoyl)-5-(4-dimethylaminotetrahydro-3-hydroxy-6-methylpyran-2-yloxy)-8,9-epoxy-2,4,6-trimethyl-3-(tetrahydro-5-hydroxy-4-methoxy-6-methylpyran-2-yloxy)nonanoic Acid μ-Lactone; Amimycin; Antibiotic PA 105; Landomycin; O
• Target: Bacterial
• Storage: -20°C
• IUPAC Name: (3R,5S,6S,7R,8S,9R,12R,13R,14S,15R)-6-[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-14-hydroxy-8-[(2R,4S,5S,6S)-5-hydroxy-4-methoxy-6-methyloxan-2-yl]oxy-5,7,9,12,13,15-hexamethyl-1,11-dioxaspiro[2.13]hexadecane-10,16-dione
• InChI: 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-,28-,29+,30-,31-,34-,35+/m0/s1
• InChIKey: RZPAKFUAFGMUPI-QESOVKLGSA-N
• SMILES: C[C@@H]1C[C@@H]([C@H]([C@@H](O1)O[C@H]2[C@H](C[C@@]3(CO3)C(=O)[C@@H]([C@H]([C@H]([C@H](OC(=O)[C@@H]([C@H]([C@@H]2C)O[C@H]4C[C@@H]([C@H]([C@@H](O4)C)O)OC)C)C)C)O)C)C)O)N(C)C

Oleandomycin（Cat No.:R052467）is a macrolide antibiotic derived from Streptomyces antibioticus, effective against various Gram-positive bacteria by inhibiting protein synthesis. It binds to the 50S subunit of bacterial ribosomes, preventing peptide chain elongation and halting bacterial growth. Oleandomycin is often used in combination with other antibiotics, like tetracycline, to enhance effectiveness, particularly in respiratory tract infections and skin infections. Though less commonly used today due to the development of newer macrolides, it remains important in research on antibiotic mechanisms and as a reference compound in microbiological studies.

Reference

Oleandomycin (PA-105). II. Chemical characterization. Els H. et al. JACS 1958, 80, 3777.The structure of oleandomycin Hochstein F.A. et al. JACS 1960, 82, 3225.