Total synthesis of albicidin: A lead structure from Xanthomonas albilineans for potent antibacterial gyrase inhibitors
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.
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Subjects: | 000 - Autres thèmes, H20 - Maladies des plantes, antimicrobien, Xanthomonas albilineans, peptide, biosynthèse, synthèse chimique, produit nouveau, acide benzoïque, http://aims.fao.org/aos/agrovoc/c_509, http://aims.fao.org/aos/agrovoc/c_27422, http://aims.fao.org/aos/agrovoc/c_5691, http://aims.fao.org/aos/agrovoc/c_928, http://aims.fao.org/aos/agrovoc/c_28580, http://aims.fao.org/aos/agrovoc/c_27804, http://aims.fao.org/aos/agrovoc/c_881, |
Online Access: | http://agritrop.cirad.fr/575752/ http://agritrop.cirad.fr/575752/1/document_575752.pdf |
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dig-cirad-fr-5757522024-01-28T22:38:00Z http://agritrop.cirad.fr/575752/ http://agritrop.cirad.fr/575752/ 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. Angewandte Chemie (International ed.), 54 (6) : 1969-1973.https://doi.org/10.1002/anie.201409584 <https://doi.org/10.1002/anie.201409584> 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 eng 2015 Angewandte Chemie (International ed.) 000 - Autres thèmes H20 - Maladies des plantes antimicrobien Xanthomonas albilineans peptide biosynthèse synthèse chimique produit nouveau acide benzoïque http://aims.fao.org/aos/agrovoc/c_509 http://aims.fao.org/aos/agrovoc/c_27422 http://aims.fao.org/aos/agrovoc/c_5691 http://aims.fao.org/aos/agrovoc/c_928 http://aims.fao.org/aos/agrovoc/c_28580 http://aims.fao.org/aos/agrovoc/c_27804 http://aims.fao.org/aos/agrovoc/c_881 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. article info:eu-repo/semantics/article Journal Article info:eu-repo/semantics/publishedVersion http://agritrop.cirad.fr/575752/1/document_575752.pdf application/pdf Cirad license info:eu-repo/semantics/restrictedAccess https://agritrop.cirad.fr/mention_legale.html https://doi.org/10.1002/anie.201409584 10.1002/anie.201409584 info:eu-repo/semantics/altIdentifier/doi/10.1002/anie.201409584 info:eu-repo/semantics/altIdentifier/purl/https://doi.org/10.1002/anie.201409584 |
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000 - Autres thèmes H20 - Maladies des plantes antimicrobien Xanthomonas albilineans peptide biosynthèse synthèse chimique produit nouveau acide benzoïque http://aims.fao.org/aos/agrovoc/c_509 http://aims.fao.org/aos/agrovoc/c_27422 http://aims.fao.org/aos/agrovoc/c_5691 http://aims.fao.org/aos/agrovoc/c_928 http://aims.fao.org/aos/agrovoc/c_28580 http://aims.fao.org/aos/agrovoc/c_27804 http://aims.fao.org/aos/agrovoc/c_881 000 - Autres thèmes H20 - Maladies des plantes antimicrobien Xanthomonas albilineans peptide biosynthèse synthèse chimique produit nouveau acide benzoïque http://aims.fao.org/aos/agrovoc/c_509 http://aims.fao.org/aos/agrovoc/c_27422 http://aims.fao.org/aos/agrovoc/c_5691 http://aims.fao.org/aos/agrovoc/c_928 http://aims.fao.org/aos/agrovoc/c_28580 http://aims.fao.org/aos/agrovoc/c_27804 http://aims.fao.org/aos/agrovoc/c_881 |
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000 - Autres thèmes H20 - Maladies des plantes antimicrobien Xanthomonas albilineans peptide biosynthèse synthèse chimique produit nouveau acide benzoïque http://aims.fao.org/aos/agrovoc/c_509 http://aims.fao.org/aos/agrovoc/c_27422 http://aims.fao.org/aos/agrovoc/c_5691 http://aims.fao.org/aos/agrovoc/c_928 http://aims.fao.org/aos/agrovoc/c_28580 http://aims.fao.org/aos/agrovoc/c_27804 http://aims.fao.org/aos/agrovoc/c_881 000 - Autres thèmes H20 - Maladies des plantes antimicrobien Xanthomonas albilineans peptide biosynthèse synthèse chimique produit nouveau acide benzoïque http://aims.fao.org/aos/agrovoc/c_509 http://aims.fao.org/aos/agrovoc/c_27422 http://aims.fao.org/aos/agrovoc/c_5691 http://aims.fao.org/aos/agrovoc/c_928 http://aims.fao.org/aos/agrovoc/c_28580 http://aims.fao.org/aos/agrovoc/c_27804 http://aims.fao.org/aos/agrovoc/c_881 Kretz, Julian Kerwat, Dennis Schubert, Vivien Grätz, Stefan Pesic, Alexander Semsary, Siamak Cociancich, Stéphane Royer, Monique Süssmuth, Roderich Total synthesis of albicidin: A lead structure from Xanthomonas albilineans for potent antibacterial gyrase inhibitors |
description |
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. |
format |
article |
topic_facet |
000 - Autres thèmes H20 - Maladies des plantes antimicrobien Xanthomonas albilineans peptide biosynthèse synthèse chimique produit nouveau acide benzoïque http://aims.fao.org/aos/agrovoc/c_509 http://aims.fao.org/aos/agrovoc/c_27422 http://aims.fao.org/aos/agrovoc/c_5691 http://aims.fao.org/aos/agrovoc/c_928 http://aims.fao.org/aos/agrovoc/c_28580 http://aims.fao.org/aos/agrovoc/c_27804 http://aims.fao.org/aos/agrovoc/c_881 |
author |
Kretz, Julian Kerwat, Dennis Schubert, Vivien Grätz, Stefan Pesic, Alexander Semsary, Siamak Cociancich, Stéphane Royer, Monique Süssmuth, Roderich |
author_facet |
Kretz, Julian Kerwat, Dennis Schubert, Vivien Grätz, Stefan Pesic, Alexander Semsary, Siamak Cociancich, Stéphane Royer, Monique Süssmuth, Roderich |
author_sort |
Kretz, Julian |
title |
Total synthesis of albicidin: A lead structure from Xanthomonas albilineans for potent antibacterial gyrase inhibitors |
title_short |
Total synthesis of albicidin: A lead structure from Xanthomonas albilineans for potent antibacterial gyrase inhibitors |
title_full |
Total synthesis of albicidin: A lead structure from Xanthomonas albilineans for potent antibacterial gyrase inhibitors |
title_fullStr |
Total synthesis of albicidin: A lead structure from Xanthomonas albilineans for potent antibacterial gyrase inhibitors |
title_full_unstemmed |
Total synthesis of albicidin: A lead structure from Xanthomonas albilineans for potent antibacterial gyrase inhibitors |
title_sort |
total synthesis of albicidin: a lead structure from xanthomonas albilineans for potent antibacterial gyrase inhibitors |
url |
http://agritrop.cirad.fr/575752/ http://agritrop.cirad.fr/575752/1/document_575752.pdf |
work_keys_str_mv |
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