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Discovery of Thanafactin A, a Linear, Proline-Containing Octalipopeptide from Pseudomonas sp. SH-C52, Motivated by Genome Mining

  • Norbert Kirchner
    Norbert Kirchner
    Pharmaceutical Institute, Department of Pharmaceutical Biology, University of Tübingen, 72076 Tübingen, Germany
  • Carolina Cano-Prieto
    Carolina Cano-Prieto
    Pharmaceutical Institute, Department of Pharmaceutical Biology, University of Tübingen, 72076 Tübingen, Germany
  • Anna-Christina Schulz-Fincke
    Anna-Christina Schulz-Fincke
    Pharmaceutical Institute, Pharmaceutical & Medicinal Chemistry, University of Bonn, 53121 Bonn, Germany
  • Michael Gütschow
    Michael Gütschow
    Pharmaceutical Institute, Pharmaceutical & Medicinal Chemistry, University of Bonn, 53121 Bonn, Germany
  • Nico Ortlieb
    Nico Ortlieb
    Department of Microbiology and Biotechnology, Interfaculty Institute of Microbiology and Infection Medicine, Eberhard Karls University Tübingen, 72076 Tübingen, Germany
    German Centre for Infection Research (DZIF), Partner Site Tübingen, 72076 Tübingen, Germany
    More by Nico Ortlieb
  • Julia Moschny
    Julia Moschny
    Department of Microbiology and Biotechnology, Interfaculty Institute of Microbiology and Infection Medicine, Eberhard Karls University Tübingen, 72076 Tübingen, Germany
  • Timo H. J. Niedermeyer
    Timo H. J. Niedermeyer
    Department of Microbiology and Biotechnology, Interfaculty Institute of Microbiology and Infection Medicine, Eberhard Karls University Tübingen, 72076 Tübingen, Germany
    German Centre for Infection Research (DZIF), Partner Site Tübingen, 72076 Tübingen, Germany
  • Jeannie Horak
    Jeannie Horak
    Pharmaceutical Institute, Department of Pharmaceutical Analysis and Bioanalysis, University of Tübingen, 72076 Tübingen, Germany
    Dr. von Hauner Children’s Hospital, Department of Metabolic and Nutritional Medicine, University of Munich Medical Center, Campus Innenstadt, 80337 Muenchen, Germany
  • Michael Lämmerhofer
    Michael Lämmerhofer
    Pharmaceutical Institute, Department of Pharmaceutical Analysis and Bioanalysis, University of Tübingen, 72076 Tübingen, Germany
  • Menno van der Voort
    Menno van der Voort
    Laboratory of Phytopathology, Wageningen University, Wageningen, Netherlands
  • Jos M. Raaijmakers
    Jos M. Raaijmakers
    Department of Microbial Ecology, Netherlands Institute of Ecology (NIOO-KNAW), Wageningen, The Netherlands
    Institute of Biology, Leiden University, Leiden, The Netherlands
  • , and 
  • Harald Gross*
    Harald Gross
    Pharmaceutical Institute, Department of Pharmaceutical Biology, University of Tübingen, 72076 Tübingen, Germany
    German Centre for Infection Research (DZIF), Partner Site Tübingen, 72076 Tübingen, Germany
    *Tel: +49-7071-2976970. Fax: +49-7071-295250. E-mail: [email protected]
    More by Harald Gross
Cite this: J. Nat. Prod. 2021, 84, 1, 101–109
Publication Date (Web):December 31, 2020
https://doi.org/10.1021/acs.jnatprod.0c01174
Copyright © 2020 American Chemical Society and American Society of Pharmacognosy
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Supporting Info (1)»

Abstract

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Genome mining of the bacterial strains Pseudomonas sp. SH-C52 and Pseudomonas fluorescens DSM 11579 showed that both strains contained a highly similar gene cluster encoding an octamodular nonribosomal peptide synthetase (NRPS) system which was not associated with a known secondary metabolite. Insertional mutagenesis of an NRPS component followed by comparative profiling led to the discovery of the corresponding novel linear octalipopeptide thanafactin A, which was subsequently isolated and its structure determined by two-dimensional NMR and further spectroscopic and chromatographic methods. In bioassays, thanafactin A exhibited weak protease inhibitory activity and was found to modulate swarming motility in a strain-specific manner.

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The Supporting Information is available free of charge at https://pubs.acs.org/doi/10.1021/acs.jnatprod.0c01174.

  • Bioinformatics analyses, spectroscopic data (HRESIMS, IR, UV, 1D, and 2D NMR spectra), enantioselective analyses, and biological assay results of compound 1 (PDF)

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Most electronic Supporting Information files are available without a subscription to ACS Web Editions. Such files may be downloaded by article for research use (if there is a public use license linked to the relevant article, that license may permit other uses). Permission may be obtained from ACS for other uses through requests via the RightsLink permission system: http://pubs.acs.org/page/copyright/permissions.html.

Cited By


This article is cited by 4 publications.

  1. Khorshed Alam, Md. Mahmudul Islam, Caiyun Li, Sharmin Sultana, Lin Zhong, Qiyao Shen, Guangle Yu, Jinfang Hao, Youming Zhang, Ruijuan Li, Aiying Li. Genome Mining of Pseudomonas Species: Diversity and Evolution of Metabolic and Biosynthetic Potential. Molecules 2021, 26 (24) , 7524. https://doi.org/10.3390/molecules26247524
  2. Aurelio Jenni, Sebastian Knüsel, Rupa Nagar, Mattias Benninger, Robert Häner, Michael A.J. Ferguson, Isabel Roditi, Anant K. Menon, Peter Bütikofer. Elimination of GPI2 suppresses glycosylphosphatidylinositol GlcNAc transferase activity and alters GPI glycan modification in Trypanosoma brucei. Journal of Biological Chemistry 2021, 297 (2) , 100977. https://doi.org/10.1016/j.jbc.2021.100977
  3. Ignacio Pérez‐Victoria. Co‐occurring Congeners Reveal the Position of Enantiomeric Amino Acids in Nonribosomal Peptides. ChemBioChem 2021, 22 (12) , 2087-2092. https://doi.org/10.1002/cbic.202000805
  4. Ryan Karongo, Junjing Jiao, Harald Gross, Michael Lämmerhofer. Direct enantioselective gradient reversed‐phase ultra‐high performance liquid chromatography tandem mass spectrometry method for 3‐hydroxy alkanoic acids in lipopeptides on an immobilized 1.6 μm amylose‐based chiral stationary phase. Journal of Separation Science 2021, 44 (9) , 1875-1883. https://doi.org/10.1002/jssc.202100104

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