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- Title
Total Synthesis of Albicidin: A Lead Structure from Xanthomonas albilineans for Potent Antibacterial Gyrase Inhibitors.
- Authors
Kretz, Julian; Kerwat, Dennis; Schubert, Vivien; Grätz, Stefan; Pesic, Alexander; Semsary, Siamak; Süssmuth, Roderich D.; Cociancich, Stéphane; Royer, Monique
- Abstract
The peptide antibiotic albicidin, which is synthesized by the plant pathogenic bacterium Xanthomonas albilineans, displays remarkable antibacterial activity against various Gram-positive and Gram-negative microorganisms. The low amounts of albicidin obtainable from the producing organism or through heterologous expression are limiting factors in providing sufficient material for bioactivity profiling and structure-activity studies. Therefore, we developed a convergent total synthesis route toward albicidin. The unexpectedly difficult formation of amide bonds between the aromatic amino acids was achieved through a triphosgene-mediated coupling strategy. The herein presented synthesis of albicidin confirms the previously determined chemical structure and underlines the extraordinary antibacterial activity of this compound. The synthetic protocol will provide multigram amounts of albicidin for further profiling of its drug properties.
- Subjects
MOLECULAR structure of peptide antibiotics; XANTHOMONAS albilineans; DNA topoisomerase II regulation; ENZYME inhibitors synthesis; BACTERIAL amino acid content; ACYL compounds; GRAM-positive bacteria; GRAM-negative bacteria
- Publication
Angewandte Chemie International Edition, 2015, Vol 54, Issue 6, p1969
- ISSN
1433-7851
- Publication type
Article
- DOI
10.1002/anie.201409584