Total synthesis and biological assessment of novel albicidins discovered by mass spectrometric networking
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.
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dig-cirad-fr-5858902024-01-29T00:37:18Z http://agritrop.cirad.fr/585890/ http://agritrop.cirad.fr/585890/ 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. Chemistry - A European Journal, 23 (61) : 15316-15321.https://doi.org/10.1002/chem.201704074 <https://doi.org/10.1002/chem.201704074> 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 eng 2017 Chemistry - A European Journal 000 - Autres thèmes H20 - Maladies des plantes L70 - Sciences et hygiène vétérinaires - Considérations générales U30 - Méthodes de recherche phytotoxine Xanthomonas albilineans biosynthèse composé biochimique antibiotique produit nouveau enzyme transférase synthèse chimique spectrométrie de masse Saccharum officinarum http://aims.fao.org/aos/agrovoc/c_34323 http://aims.fao.org/aos/agrovoc/c_27422 http://aims.fao.org/aos/agrovoc/c_928 http://aims.fao.org/aos/agrovoc/c_92336 http://aims.fao.org/aos/agrovoc/c_492 http://aims.fao.org/aos/agrovoc/c_27804 http://aims.fao.org/aos/agrovoc/c_2603 http://aims.fao.org/aos/agrovoc/c_7865 http://aims.fao.org/aos/agrovoc/c_28580 http://aims.fao.org/aos/agrovoc/c_12421 http://aims.fao.org/aos/agrovoc/c_6727 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. article info:eu-repo/semantics/article Journal Article info:eu-repo/semantics/publishedVersion http://agritrop.cirad.fr/585890/1/von-Eckardstein_et_al-2017-Chemistry_-_A_European_Journal.pdf text Cirad license info:eu-repo/semantics/restrictedAccess https://agritrop.cirad.fr/mention_legale.html https://doi.org/10.1002/chem.201704074 10.1002/chem.201704074 info:eu-repo/semantics/altIdentifier/doi/10.1002/chem.201704074 info:eu-repo/semantics/altIdentifier/purl/https://doi.org/10.1002/chem.201704074 |
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000 - Autres thèmes H20 - Maladies des plantes L70 - Sciences et hygiène vétérinaires - Considérations générales U30 - Méthodes de recherche phytotoxine Xanthomonas albilineans biosynthèse composé biochimique antibiotique produit nouveau enzyme transférase synthèse chimique spectrométrie de masse Saccharum officinarum http://aims.fao.org/aos/agrovoc/c_34323 http://aims.fao.org/aos/agrovoc/c_27422 http://aims.fao.org/aos/agrovoc/c_928 http://aims.fao.org/aos/agrovoc/c_92336 http://aims.fao.org/aos/agrovoc/c_492 http://aims.fao.org/aos/agrovoc/c_27804 http://aims.fao.org/aos/agrovoc/c_2603 http://aims.fao.org/aos/agrovoc/c_7865 http://aims.fao.org/aos/agrovoc/c_28580 http://aims.fao.org/aos/agrovoc/c_12421 http://aims.fao.org/aos/agrovoc/c_6727 000 - Autres thèmes H20 - Maladies des plantes L70 - Sciences et hygiène vétérinaires - Considérations générales U30 - Méthodes de recherche phytotoxine Xanthomonas albilineans biosynthèse composé biochimique antibiotique produit nouveau enzyme transférase synthèse chimique spectrométrie de masse Saccharum officinarum http://aims.fao.org/aos/agrovoc/c_34323 http://aims.fao.org/aos/agrovoc/c_27422 http://aims.fao.org/aos/agrovoc/c_928 http://aims.fao.org/aos/agrovoc/c_92336 http://aims.fao.org/aos/agrovoc/c_492 http://aims.fao.org/aos/agrovoc/c_27804 http://aims.fao.org/aos/agrovoc/c_2603 http://aims.fao.org/aos/agrovoc/c_7865 http://aims.fao.org/aos/agrovoc/c_28580 http://aims.fao.org/aos/agrovoc/c_12421 http://aims.fao.org/aos/agrovoc/c_6727 |
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000 - Autres thèmes H20 - Maladies des plantes L70 - Sciences et hygiène vétérinaires - Considérations générales U30 - Méthodes de recherche phytotoxine Xanthomonas albilineans biosynthèse composé biochimique antibiotique produit nouveau enzyme transférase synthèse chimique spectrométrie de masse Saccharum officinarum http://aims.fao.org/aos/agrovoc/c_34323 http://aims.fao.org/aos/agrovoc/c_27422 http://aims.fao.org/aos/agrovoc/c_928 http://aims.fao.org/aos/agrovoc/c_92336 http://aims.fao.org/aos/agrovoc/c_492 http://aims.fao.org/aos/agrovoc/c_27804 http://aims.fao.org/aos/agrovoc/c_2603 http://aims.fao.org/aos/agrovoc/c_7865 http://aims.fao.org/aos/agrovoc/c_28580 http://aims.fao.org/aos/agrovoc/c_12421 http://aims.fao.org/aos/agrovoc/c_6727 000 - Autres thèmes H20 - Maladies des plantes L70 - Sciences et hygiène vétérinaires - Considérations générales U30 - Méthodes de recherche phytotoxine Xanthomonas albilineans biosynthèse composé biochimique antibiotique produit nouveau enzyme transférase synthèse chimique spectrométrie de masse Saccharum officinarum http://aims.fao.org/aos/agrovoc/c_34323 http://aims.fao.org/aos/agrovoc/c_27422 http://aims.fao.org/aos/agrovoc/c_928 http://aims.fao.org/aos/agrovoc/c_92336 http://aims.fao.org/aos/agrovoc/c_492 http://aims.fao.org/aos/agrovoc/c_27804 http://aims.fao.org/aos/agrovoc/c_2603 http://aims.fao.org/aos/agrovoc/c_7865 http://aims.fao.org/aos/agrovoc/c_28580 http://aims.fao.org/aos/agrovoc/c_12421 http://aims.fao.org/aos/agrovoc/c_6727 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 Total synthesis and biological assessment of novel albicidins discovered by mass spectrometric networking |
description |
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. |
format |
article |
topic_facet |
000 - Autres thèmes H20 - Maladies des plantes L70 - Sciences et hygiène vétérinaires - Considérations générales U30 - Méthodes de recherche phytotoxine Xanthomonas albilineans biosynthèse composé biochimique antibiotique produit nouveau enzyme transférase synthèse chimique spectrométrie de masse Saccharum officinarum http://aims.fao.org/aos/agrovoc/c_34323 http://aims.fao.org/aos/agrovoc/c_27422 http://aims.fao.org/aos/agrovoc/c_928 http://aims.fao.org/aos/agrovoc/c_92336 http://aims.fao.org/aos/agrovoc/c_492 http://aims.fao.org/aos/agrovoc/c_27804 http://aims.fao.org/aos/agrovoc/c_2603 http://aims.fao.org/aos/agrovoc/c_7865 http://aims.fao.org/aos/agrovoc/c_28580 http://aims.fao.org/aos/agrovoc/c_12421 http://aims.fao.org/aos/agrovoc/c_6727 |
author |
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 |
author_facet |
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 |
author_sort |
Von Eckardstein, Leonard |
title |
Total synthesis and biological assessment of novel albicidins discovered by mass spectrometric networking |
title_short |
Total synthesis and biological assessment of novel albicidins discovered by mass spectrometric networking |
title_full |
Total synthesis and biological assessment of novel albicidins discovered by mass spectrometric networking |
title_fullStr |
Total synthesis and biological assessment of novel albicidins discovered by mass spectrometric networking |
title_full_unstemmed |
Total synthesis and biological assessment of novel albicidins discovered by mass spectrometric networking |
title_sort |
total synthesis and biological assessment of novel albicidins discovered by mass spectrometric networking |
url |
http://agritrop.cirad.fr/585890/ http://agritrop.cirad.fr/585890/1/von-Eckardstein_et_al-2017-Chemistry_-_A_European_Journal.pdf |
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