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Title: Tundrenone: An Atypical Secondary Metabolite from Bacteria with Highly Restricted Primary Metabolism

Abstract

Methane-oxidizing bacteria, aerobes that utilize methane as their sole carbon and energy source, are being increasingly studied for their environmentally significant ability to remove methane from the atmosphere. Their genomes indicate that they also have a robust and unusual secondary metabolism. Bioinformatic analysis of the Methylobacter tundripaludum genome identified biosynthetic gene clusters for several intriguing metabolites, and this report discloses the structural and genetic characterization of tundrenone, one of these metabolites. Tundrenone is a highly oxidized metabolite that incorporates both a modified bicyclic chorismate-derived fragment and a modified lipid tail bearing a β,γ-unsaturated α-hydroxy ketone. Tundrenone has been genetically linked to its biosynthetic gene cluster, and quorum sensing activates its production. M. tundripaludum’s genome and tundrenone’s discovery support the idea that additional studies of methane-oxidizing bacteria will reveal new naturally occurring molecular scaffolds and the biosynthetic pathways that produce them.

Authors:
 [1];  [2]; ORCiD logo [2]; ORCiD logo [3];  [1];  [4]; ORCiD logo [3]; ORCiD logo [5];  [6]; ORCiD logo [2]
  1. Department of Chemical Engineering, University of Washington, Seattle, Washington 98195, United States
  2. Department of Biological Chemistry and Molecular Pharmacology, Harvard Medical School, 240 Longwood Avenue, Boston, Massachusetts 02115, United States
  3. Collaborative Mass Spectrometry Innovation Center, Skaggs School of Pharmacy and Pharmaceutical Sciences, University of California, San Diego, La Jolla, California 92093, United States
  4. Institute of Microbiology, Eidgenössische Technische Hochschule (ETH) Zürich, Vladimir-Prelog-Weg 4, 8093 Zürich, Switzerland
  5. Department of Microbiology, University of Washington, Seattle, Washington 98195, United States
  6. Department of Chemical Engineering, University of Washington, Seattle, Washington 98195, United States, Department of Microbiology, University of Washington, Seattle, Washington 98195, United States
Publication Date:
Research Org.:
Harvard Medical School, Boston, MA (United States)
Sponsoring Org.:
USDOE Office of Science (SC), Biological and Environmental Research (BER) (SC-23)
OSTI Identifier:
1418731
Alternate Identifier(s):
OSTI ID: 1529570
Grant/Contract Number:  
SC0010556
Resource Type:
Published Article
Journal Name:
Journal of the American Chemical Society
Additional Journal Information:
Journal Name: Journal of the American Chemical Society Journal Volume: 140 Journal Issue: 6; Journal ID: ISSN 0002-7863
Publisher:
American Chemical Society (ACS)
Country of Publication:
United States
Language:
English
Subject:
59 BASIC BIOLOGICAL SCIENCES; 37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY

Citation Formats

Puri, Aaron W., Mevers, Emily, Ramadhar, Timothy R., Petras, Daniel, Liu, Darren, Piel, Jörn, Dorrestein, Pieter C., Greenberg, E. Peter, Lidstrom, Mary E., and Clardy, Jon. Tundrenone: An Atypical Secondary Metabolite from Bacteria with Highly Restricted Primary Metabolism. United States: N. p., 2018. Web. doi:10.1021/jacs.7b12240.
Puri, Aaron W., Mevers, Emily, Ramadhar, Timothy R., Petras, Daniel, Liu, Darren, Piel, Jörn, Dorrestein, Pieter C., Greenberg, E. Peter, Lidstrom, Mary E., & Clardy, Jon. Tundrenone: An Atypical Secondary Metabolite from Bacteria with Highly Restricted Primary Metabolism. United States. doi:10.1021/jacs.7b12240.
Puri, Aaron W., Mevers, Emily, Ramadhar, Timothy R., Petras, Daniel, Liu, Darren, Piel, Jörn, Dorrestein, Pieter C., Greenberg, E. Peter, Lidstrom, Mary E., and Clardy, Jon. Tue . "Tundrenone: An Atypical Secondary Metabolite from Bacteria with Highly Restricted Primary Metabolism". United States. doi:10.1021/jacs.7b12240.
@article{osti_1418731,
title = {Tundrenone: An Atypical Secondary Metabolite from Bacteria with Highly Restricted Primary Metabolism},
author = {Puri, Aaron W. and Mevers, Emily and Ramadhar, Timothy R. and Petras, Daniel and Liu, Darren and Piel, Jörn and Dorrestein, Pieter C. and Greenberg, E. Peter and Lidstrom, Mary E. and Clardy, Jon},
abstractNote = {Methane-oxidizing bacteria, aerobes that utilize methane as their sole carbon and energy source, are being increasingly studied for their environmentally significant ability to remove methane from the atmosphere. Their genomes indicate that they also have a robust and unusual secondary metabolism. Bioinformatic analysis of the Methylobacter tundripaludum genome identified biosynthetic gene clusters for several intriguing metabolites, and this report discloses the structural and genetic characterization of tundrenone, one of these metabolites. Tundrenone is a highly oxidized metabolite that incorporates both a modified bicyclic chorismate-derived fragment and a modified lipid tail bearing a β,γ-unsaturated α-hydroxy ketone. Tundrenone has been genetically linked to its biosynthetic gene cluster, and quorum sensing activates its production. M. tundripaludum’s genome and tundrenone’s discovery support the idea that additional studies of methane-oxidizing bacteria will reveal new naturally occurring molecular scaffolds and the biosynthetic pathways that produce them.},
doi = {10.1021/jacs.7b12240},
journal = {Journal of the American Chemical Society},
number = 6,
volume = 140,
place = {United States},
year = {2018},
month = {1}
}

Journal Article:
Free Publicly Available Full Text
Publisher's Version of Record
DOI: 10.1021/jacs.7b12240

Citation Metrics:
Cited by: 3 works
Citation information provided by
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Figures / Tables:

Figure 1 Figure 1: (a) Structure of tundrenone (1). (b) Partial structures assembled by 2D NMR data.

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Works referencing / citing this record:

Vinylogous Reactivity of Cyclic 2-Enones: Organocatalysed Asymmetric Addition to 2-Enals to Synthesize Fused Carbocycles
journal, April 2019

  • Sofiadis, Manolis; Kalaitzakis, Dimitris; Sarris, John
  • Angewandte Chemie International Edition, Vol. 58, Issue 20
  • DOI: 10.1002/anie.201901902

Vinylogous Reactivity of Cyclic 2-Enones: Organocatalysed Asymmetric Addition to 2-Enals to Synthesize Fused Carbocycles
journal, April 2019

  • Sofiadis, Manolis; Kalaitzakis, Dimitris; Sarris, John
  • Angewandte Chemie International Edition, Vol. 58, Issue 20
  • DOI: 10.1002/anie.201901902

    Figures/Tables have been extracted from DOE-funded journal article accepted manuscripts.