Hydrophobic acetal and ketal derivatives of mannopeptimycin-α and desmethylhexahydromannopeptimycin-α: Semisynthetic glycopeptides with potent activity against Gram-positive bacteria

Russell G. Dushin, Ting Zhong Wang, Phaik Eng Sum, Haiyin He, Alan G. Sutherland, Joseph S. Ashcroft, Edmund I. Graziani, Frank E. Koehn, Patricia A. Bradford, Peter J. Petersen, Karen L. Wheless, David How, Nancy Torres, Eileen B. Lenoy, William J. Weiss, Stanley A. Lang, Steven J. Projan, David M. Shlaes, Tarek S. Mansour

Research output: Contribution to journalArticle

32 Scopus citations

Abstract

The effect of introducing hydrophobic groups onto the disaccharide portion of the mannopeptimycins has been examined. Under acid-catalyzed conditions dimethyl acetals and ketals react on the terminal mannose of the disaccharide moiety of mannopeptimycin-α and the cyclohexylalanyl analogue 2. The preferentially formed monofunctionalized 4,6-acetals and -ketals display potent antibacterial activities against Gram-positive microorganisms, including MRSA, PRSP, and VRE pathogens.

Original languageEnglish
Pages (from-to)3487-3490
Number of pages4
JournalJournal of Medicinal Chemistry
Volume47
Issue number14
DOIs
StatePublished - 1 Jul 2004

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    Dushin, R. G., Wang, T. Z., Sum, P. E., He, H., Sutherland, A. G., Ashcroft, J. S., Graziani, E. I., Koehn, F. E., Bradford, P. A., Petersen, P. J., Wheless, K. L., How, D., Torres, N., Lenoy, E. B., Weiss, W. J., Lang, S. A., Projan, S. J., Shlaes, D. M., & Mansour, T. S. (2004). Hydrophobic acetal and ketal derivatives of mannopeptimycin-α and desmethylhexahydromannopeptimycin-α: Semisynthetic glycopeptides with potent activity against Gram-positive bacteria. Journal of Medicinal Chemistry, 47(14), 3487-3490. https://doi.org/10.1021/jm049765y