Mannopeptimycin esters and carbonates, potent antibiotic agents against drug-resistant bacteria

• Published in: Bioorganic & medicinal chemistry letters Vol. 14; no. 1; pp. 279 - 282
• Main Authors: He, Haiyin, Shen, Bo, Petersen, Peter J., Weiss, William J., Yang, Hui Y., Wang, Ting-Zhong, Dushin, Russell G., Koehn, Frank E., Carter, Guy T.
• Format: Journal Article
• Language: English
• Published: Oxford Elsevier Ltd 05.01.2004; Elsevier
• Subjects: Animals; Anti-Bacterial Agents - chemistry; Anti-Bacterial Agents - pharmacology; Antibacterial agents; Antibiotics. Antiinfectious agents. Antiparasitic agents; Biological and medical sciences; Carbonates - chemistry; Carbonates - pharmacology; Drug Resistance, Multiple, Bacterial - drug effects; Drug Resistance, Multiple, Bacterial - physiology; Esters; Glycopeptides; Medical sciences; Mice; Microbial Sensitivity Tests - statistics & numerical data; Pharmacology. Drug treatments; Staphylococcus aureus - drug effects; Staphylococcus aureus - growth & development; Enterococcus faecalis; Organic carbonate; Cyclic peptides; Hexapeptide; Resistance; Streptococcaceae; Ester; Chemical modification; Structure activity relation; Glycopeptide; Bacteria; Micrococcales; Micrococcaceae; Antibacterial agent; Staphylococcus aureus; Hemisynthesis
• ISSN: 0960-894X; 1464-3405
• DOI: 10.1016/j.bmcl.2003.09.071

A series of ester and carbonate derivatives of the glycopeptide mannopeptimycin α ( 1) with potent activity against G(+) bacteria, including the methicillin-resistant staphylococci and vancomycin-resistant enterococci, was synthesized. The SAR data obtained from natural and semisynthetic compounds demonstrated the importance of a hydrophobic group in the terminal mannosyl moiety for antibacterial activity. A series of ester and carbonate derivatives of the glycopeptide mannopeptimycin α with potent activity against drug-resistant G(+) bacteria was synthesized.