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Progress toward Total Solid-Phase Synthesis of Depsipeptide Antibiotic Katanosin B

  • Roma Stawikowska
  • Maciej Stawikowski
  • Predrag Cudic
Part of the Advances in Experimental Medicine and Biology book series (volume 611)

Introduction

The peptidoglycan synthesis pathway is an attractive target for antibacterial and antifungal agents in terms of specificity for microorganisms. Drugs with different mode of action from vancomycin should be promising candidates against vancomycin resistant strains. Katanosin B is naturally occurring cyclic depsipeptide antibiotic isolated from strain related to the genus Cytophaga.1According to recent literature data it inhibits transglycosylation and transpeptidation steps of bacterial cell wall biosynthesis by an unidentified mechanism that differs from those of vancomycin. Katanosin B is composed of eleven amino acids from which nine form cyclic structure joined with one ester linkage. In addition, this antibiotic contains three unusual L-β-hydroxy amino acids: phenylserine (PhSer), hydroxyleucine (HyLeu) and hydroxyasparagine (HyAsn). Lack of commercial sources of katanosin B producing organism PBJ-5356 and, particularly, unlimited access to its synthetic analogs...

Keywords

Benzyl Alcohol Active Charcoal Unusual Amino Acid Eleven Amino Acid Important Natural Product 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

Notes

Acknowledgments

The work was funded by an AHA-SDG grant (0630175N) to P. Cudic.

References

  1. 1.
    Maki, H., Miura, K., Yamano, Y., Antimicrob. Agents Chemother. 45, 1823–1827 (2001)CrossRefGoogle Scholar
  2. 2.
    Stawikowski, M., Cudic, P. Tetrahedron Lett. 47, 8587–8590 (2006)CrossRefGoogle Scholar
  3. 3.
    Jung, M. E., Jung, Y., H. Tetrahedron Lett., 30, 6637–6640 (1989)CrossRefGoogle Scholar
  4. 4.
    Boger, D. L., Lee, R. J., Bounaud, P. Y., Meier, P. J. Org. Chem. 65, 6770–6772 (2000)CrossRefGoogle Scholar
  5. 5.
    Chenault, H. K., Dahmer, J., Whitesides, G. M. J. Am. Chem. Soc. 111, 6354–6364 (1989)CrossRefGoogle Scholar

Copyright information

© Springer Science+Business Media, LLC 2009

Authors and Affiliations

  • Roma Stawikowska
    • 1
  • Maciej Stawikowski
    • 1
  • Predrag Cudic
    • 1
  1. 1.Department of Chemistry and BiochemistryFlorida Atlantic UniversityBoca RatonUSA

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