Total synthesis and biological assessment of novel albicidins discovered by mass spectrometric networking

Von Eckardstein Leonard, Petras Daniel, Dang Tam, Cociancich Stéphane, Sabri Souhir, Grätz Stefan, Kerwat Dennis, Seidel Maria, Pesic Alexander, Dorrestein Pieter C., Royer Monique, Weston John B., Süssmuth Roderich. 2017. Total synthesis and biological assessment of novel albicidins discovered by mass spectrometric networking. Chemistry - A European Journal, 23 (61) : 15316-15321.

Quartile : Q1, Sujet : CHEMISTRY, MULTIDISCIPLINARY

Résumé : Natural products represent an important source of potential novel antimicrobial drug leads. Low production by microorganisms in cell culture often delays the structural elucidation or even prevents a timely discovery. Starting from the anti-Gram-negative antibacterial compound albicidin produced by Xanthomonas albilineans, we describe a bioactivity-guided approach combined with non-targeted tandem mass spectrometry and spectral (molecular) networking for the discovery of novel antimicrobial compounds. We report eight new natural albicidin derivatives, four of which bear a β-methoxy cyanoalanine or β-methoxy asparagine as the central α-amino acid. We present the total synthesis of these albicidins, which facilitated the unambiguous determination of the (2 S,3 R)-stereoconfiguration which is complemented by the assessment of the stereochemistry on antibacterial activity.

Mots-clés Agrovoc : phytotoxine, Xanthomonas albilineans, biosynthèse, composé biochimique, antibiotique, produit nouveau, enzyme, transférase, synthèse chimique, spectrométrie de masse, Saccharum officinarum

Mots-clés complémentaires : Albicidine

Classification Agris : 000 - Autres thèmes
H20 - Maladies des plantes
L70 - Sciences et hygiène vétérinaires - Considérations générales
U30 - Méthodes de recherche

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

Auteurs et affiliations

• Von Eckardstein Leonard, Technische Universitaet Berlin (DEU)
• Petras Daniel, Technische Universitaet Berlin (DEU)
• Dang Tam, Technische Universitaet Berlin (DEU)
• Cociancich Stéphane, CIRAD-BIOS-UMR BGPI (FRA) ORCID: 0000-0001-8601-3598
• Sabri Souhir, CIRAD-BIOS-UMR BGPI (FRA)
• Grätz Stefan, Technische Universitaet Berlin (DEU)
• Kerwat Dennis, Technische Universitaet Berlin (DEU)
• Seidel Maria, Technische Universitaet Berlin (DEU)
• Pesic Alexander, Technische Universitaet Berlin (DEU)
• Dorrestein Pieter C., Skaggs School of Pharmacy and Pharmaceutical Sciences (USA)
• Royer Monique, CIRAD-BIOS-UMR BGPI (FRA)
• Weston John B., Technische Universitaet Berlin (DEU)
• Süssmuth Roderich, Technische Universitaet Berlin (DEU) - auteur correspondant

Source : Cirad-Agritrop (https://agritrop.cirad.fr/585890/)

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