Total synthesis of albicidin: A lead structure from Xanthomonas albilineans for potent antibacterial gyrase inhibitors

Kretz Julian, Kerwat Dennis, Schubert Vivien, Grätz Stefan, Pesic Alexander, Semsary Siamak, Cociancich Stéphane, Royer Monique, Süssmuth Roderich. 2015. Total synthesis of albicidin: A lead structure from Xanthomonas albilineans for potent antibacterial gyrase inhibitors. Angewandte Chemie (International ed.), 54 (6) : 1969-1973.

Quartile : Outlier, Sujet : CHEMISTRY, MULTIDISCIPLINARY

Résumé : 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.

Mots-clés Agrovoc : antimicrobien, Xanthomonas albilineans, peptide, biosynthèse, synthèse chimique, produit nouveau, acide benzoïque

Mots-clés complémentaires : Albicidine

Classification Agris : 000 - Autres thèmes
H20 - Maladies des plantes

Champ stratégique Cirad : Axe 4 (2014-2018) - Santé des animaux et des plantes

Auteurs et affiliations

• Kretz Julian, Technische Universitaet Berlin (DEU)
• Kerwat Dennis, Technische Universitaet Berlin (DEU)
• Schubert Vivien, Technische Universitaet Berlin (DEU)
• Grätz Stefan, Technische Universitaet Berlin (DEU)
• Pesic Alexander, Technische Universitaet Berlin (DEU)
• Semsary Siamak, Technische Universitaet Berlin (DEU)
• Cociancich Stéphane, CIRAD-BIOS-UMR BGPI (FRA)
• Royer Monique, CIRAD-BIOS-UMR BGPI (FRA)
• Süssmuth Roderich, Technische Universitaet Berlin (DEU)

Source : Cirad - Agritrop (https://agritrop.cirad.fr/575752/)

Métriques

[ Page générée et mise en cache le 2024-04-24 ]