Chloroeremomycin
Glycopeptide antibiotic precursor to oritavancin, produced by Amycolatopsis orientalis with activity against vancomycin-resistant organisms.
Chemical Identity
| Property | Value |
|---|---|
| Chemical Formula | C73H88Cl2N10O26 |
| Molecular Weight | 1578.4 Da |
| Peptide Class | Glycopeptide Antibiotic |
| Origin | Amycolatopsis orientalis |
Structure
Chloroeremomycin is a heptapeptide glycopeptide with three fused aromatic rings, similar to vancomycin, but with an additional 4-epi-vancosamine sugar that provides enhanced binding to D-Ala-D-Ala. The chlorine atoms are on the biphenyl ring system, and the epivancosamine disaccharide distinguishes it from vancomycin.
Mechanism of Action
Like vancomycin, chloroeremomycin binds the D-alanyl-D-alanine terminus of peptidoglycan precursors, inhibiting cell wall transglycosylation and transpeptidation. The additional sugar moiety provides enhanced membrane anchoring and improved activity against some vancomycin-intermediate strains.
Clinical Applications
- Precursor to oritavancin: Semi-synthetic modification yields oritavancin
- Research use: Study of glycopeptide structure-activity relationships
- Not used clinically: Parent compound; oritavancin is the clinical derivative
Pharmacology
Chloroeremomycin demonstrates similar but slightly improved activity compared to vancomycin against gram-positive bacteria. It retains activity against some vanB VRE strains due to enhanced binding kinetics.
References
- Nagarajan, R., et al. (1989). Antibiotic activities of chloroeremomycin. Antimicrobial Agents and Chemotherapy, 33, 1073-1078.
- Allen, N.E., & Nicas, T.I. (2003). Mechanism of action of oritavancin. FEMS Microbiology Reviews, 26, 511-532.
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