Methylobacter species, members of the Methylococcales, have recently emerged as some of the globally widespread, cosmopolitan species that play a key role in the environmental consumption of methane across gradients of dioxygen tensions. Publication Date: Research Org.: Harvard Medical School, Boston, MA (United States) Sponsoring Org.: USDOE Office of Science (SC), Biological and Environmental Research (BER) 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 = , Departmentof Chemical Engineering, University of Washington, Seattle, Washington 98195, United States, Departmentof Microbiology, University of Washington, Seattle, Washington 98195, United States.

Departmentof Microbiology, University of Washington, Seattle, Washington 98195, United States.Instituteof Microbiology, Eidgenössische Technische Hochschule (ETH) Zürich, Vladimir-Prelog-Zürich, Switzerland.CollaborativeMass Spectrometry Innovation Center, Skaggs School of Pharmacy andPharmaceutical Sciences, University of California, San Diego, La Jolla, California 92093, United States.Departmentof Biological Chemistry and Molecular Pharmacology, Harvard Medical School, 240 Longwood Avenue, Boston, Massachusetts 02115, United States.Departmentof Chemical Engineering, University of Washington, Seattle, Washington 98195, United States.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. Tundrenone has been genetically linked to its biosynthetic gene cluster, and quorum sensing activates its production. 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. 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. Their genomes indicate that they also have a robust and unusual secondary metabolism. 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.

Atypical bacteria shapes