Isolation and structure of a new macrolide antibiotic, erythromycin G, and a related biosynthetic intermediate from a culture of Saccharopolyspora erythraea.
The new naturally occurring erythromycin G (4), formally derived from erythromycin B by hydroxylation of the C-16 methyl group, and 3-O-mycarosylerythronolide B (5), an erythromycin biosynthetic intermediate previously obtained only from microorganisms blocked in erythromycin biosynthesis, were isolated from a concentrate of mother liquors derived from a culture of Saccharopolyspora erythraea. The structure of erythromycin G was defined by spectroscopic data and X-ray crystallographic analysis. Theoretical calculation of 4 has been performed at MM2 level, and the low-energy conformations have been compared with X-ray data: both theoretical and experimental approaches give similar three-dimensional shapes. Antibacterial activity of 4 against both gram-positive and gram-negative organisms has been evaluated. A simple method for the isolation of large amounts of erythromycins B (2) and D is provided as well.
Cevallos
Alexandre
A
Biotechnical Research & Development, Biochemie S.p.A., corso Verona 165, 38068 Rovereto, Trento, Italy.
Guerriero
Antonio
A
D000900:Anti-Bacterial Agents / Q000096:biosynthesis / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D002851:Chromatography, High Pressure Liquid; D018360:Crystallography, X-Ray; D004917:Erythromycin / Q000031:analogs & derivatives / Q000096:biosynthesis / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D006090:Gram-Negative Bacteria / Q000145:classification / Q000187:drug effects; D006094:Gram-Positive Bacteria / Q000145:classification / Q000187:drug effects; D008826:Microbial Sensitivity Tests; D008958:Models, Molecular; D015394:Molecular Structure
D000900:Anti-Bacterial Agents; C474718:erythromycin G; D004917:Erythromycin