Vancomycin, teicoplanin, and ramoplanin: synthetic and mechanistic studies.
Vancomycin, teicoplanin, and ramoplanin are potent glycopeptide antibiotics that act by inhibiting bacterial cell wall biosynthesis. The former are used clinically as the antibiotics of last resort for the treatment of methicillin-resistant Staphylococcus aureus and the latter is a promising new antibiotic that is not susceptible to the emerging bacterial resistance to vancomycin and teicoplanin. A summary of our recent total synthesis of the vancomycin aglycon, our first and second generation total syntheses of the teicoplanin aglycon, and our progress on the total synthesis of the ramoplanins is presented. This work lays the foundation for ongoing structure-function studies on the antibiotics that may clarify or define their site and mechanism of action leading to the development of improved or reengineered antibiotics.
Boger
D L
DL
Department of Chemistry and the Skaggs Institute for Chemical Biology, The Scripps Research Institute, La Jolla, California 92037, USA. boger@scripps.edu
D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D047630:Depsipeptides; D010456:Peptides, Cyclic; D017334:Teicoplanin / Q000138:chemical synthesis* / Q000494:pharmacology; D014640:Vancomycin / Q000138:chemical synthesis* / Q000494:pharmacology
D000900:Anti-Bacterial Agents; D047630:Depsipeptides; D010456:Peptides, Cyclic; C041438:ramoplanin; D017334:Teicoplanin; D014640:Vancomycin