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Muriel Gugger
Institut Pasteur Collection des Cyanobactéries Département de Microbiologie 75015 Paris France

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Communication
Published: 14 February 2021 in Angewandte Chemie International Edition
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Cyanobactins comprise a widespread group of peptide metabolites produced by cyanobacteria that are often diversified by post‐translational prenylation. Several enzymes have been identified in cyanobactin biosynthetic pathways that carry out chemically diverse prenylation reactions, representing a resource for the discovery of post‐translational alkylating agents. Here, genome mining was used to identify orphan cyanobactin prenyltransferases, leading to isolation of tolypamide from the freshwater cyanobacterium, Tolypothrix sp. The structure of tolypamide was confirmed by spectroscopic methods, degradation, and enzymatic total synthesis. Tolypamide is forward prenylated on a threonine residue, representing an unprecedented post‐translational modification. Biochemical characterization of cognate enzyme TolF revealed a prenyltransferase with strict selectivity for forward O ‐prenylation of serine or threonine, but with relaxed substrate selectivity for flanking peptide sequences. Since cyanobactin pathways often exhibit exceptionally broad substrate tolerance, these enzymes represent robust tools for synthetic biology.

ACS Style

Mugilarasi Purushothaman; Snigdha Sarkar; Maho Morita; Muriel Gugger; Eric W. Schmidt; Brandon I. Morinaka. Genome‐Mining‐Based Discovery of the Cyclic Peptide Tolypamide and TolF, a Ser/Thr Forward O ‐Prenyltransferase. Angewandte Chemie International Edition 2021, 60, 8460 -8465.

AMA Style

Mugilarasi Purushothaman, Snigdha Sarkar, Maho Morita, Muriel Gugger, Eric W. Schmidt, Brandon I. Morinaka. Genome‐Mining‐Based Discovery of the Cyclic Peptide Tolypamide and TolF, a Ser/Thr Forward O ‐Prenyltransferase. Angewandte Chemie International Edition. 2021; 60 (15):8460-8465.

Chicago/Turabian Style

Mugilarasi Purushothaman; Snigdha Sarkar; Maho Morita; Muriel Gugger; Eric W. Schmidt; Brandon I. Morinaka. 2021. "Genome‐Mining‐Based Discovery of the Cyclic Peptide Tolypamide and TolF, a Ser/Thr Forward O ‐Prenyltransferase." Angewandte Chemie International Edition 60, no. 15: 8460-8465.

Communication
Published: 14 February 2021 in Angewandte Chemie
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Cyanobactins comprise a widespread group of peptide metabolites produced by cyanobacteria that are often diversified by post‐translational prenylation. Several enzymes have been identified in cyanobactin biosynthetic pathways that carry out chemically diverse prenylation reactions, representing a resource for the discovery of post‐translational alkylating agents. Here, genome mining was used to identify orphan cyanobactin prenyltransferases, leading to isolation of tolypamide from the freshwater cyanobacterium, Tolypothrix sp. The structure of tolypamide was confirmed by spectroscopic methods, degradation, and enzymatic total synthesis. Tolypamide is forward prenylated on a threonine residue, representing an unprecedented post‐translational modification. Biochemical characterization of cognate enzyme TolF revealed a prenyltransferase with strict selectivity for forward O ‐prenylation of serine or threonine, but with relaxed substrate selectivity for flanking peptide sequences. Since cyanobactin pathways often exhibit exceptionally broad substrate tolerance, these enzymes represent robust tools for synthetic biology.

ACS Style

Mugilarasi Purushothaman; Snigdha Sarkar; Maho Morita; Muriel Gugger; Eric W. Schmidt; Brandon I. Morinaka. Genome‐Mining‐Based Discovery of the Cyclic Peptide Tolypamide and TolF, a Ser/Thr Forward O ‐Prenyltransferase. Angewandte Chemie 2021, 133, 8541 -8546.

AMA Style

Mugilarasi Purushothaman, Snigdha Sarkar, Maho Morita, Muriel Gugger, Eric W. Schmidt, Brandon I. Morinaka. Genome‐Mining‐Based Discovery of the Cyclic Peptide Tolypamide and TolF, a Ser/Thr Forward O ‐Prenyltransferase. Angewandte Chemie. 2021; 133 (15):8541-8546.

Chicago/Turabian Style

Mugilarasi Purushothaman; Snigdha Sarkar; Maho Morita; Muriel Gugger; Eric W. Schmidt; Brandon I. Morinaka. 2021. "Genome‐Mining‐Based Discovery of the Cyclic Peptide Tolypamide and TolF, a Ser/Thr Forward O ‐Prenyltransferase." Angewandte Chemie 133, no. 15: 8541-8546.

Review
Published: 30 November 2020 in Discover Materials
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Although biomineralization of CaCO3 is widespread in Bacteria and Archaea, the molecular mechanisms involved in this process remain less known than those used by Eukaryotes. A better understanding of these mechanisms is crucial for a broad diversity of studies including those (i) aiming at assessing the role of bacteria in the geochemical cycles of Ca and C, (ii) investigating the process of fossilization, and (iii) engineering applications using bacterially mediated CaCO3 mineralization. Different types of bacterially-mediated mineralization modes have been distinguished depending on whether they are influenced (by extracellular organic molecules), induced (by metabolic activity) or controlled (by specific genes). In the first two types, mineralization is usually extracellular, while it is intracellular for the two ascertained cases of controlled bacterial mineralization. In this review, we list a large number of cases illustrating the three different modes of bacterially-mediated CaCO3 mineralization. Overall, this shows the broad diversity of metabolic pathways, organic molecules and thereby microorganisms that can biomineralize CaCO3. Providing an improved understanding of the mechanisms involved and a good knowledge of the molecular drivers of carbonatogenesis, the increasing number of (meta)-omics studies may help in the future to estimate the significance of bacterially mediated CaCO3 mineralization.

ACS Style

Sigrid Görgen; Karim Benzerara; Fériel Skouri-Panet; Muriel Gugger; Franck Chauvat; Corinne Cassier-Chauvat. The diversity of molecular mechanisms of carbonate biomineralization by bacteria. Discover Materials 2020, 1, 1 -20.

AMA Style

Sigrid Görgen, Karim Benzerara, Fériel Skouri-Panet, Muriel Gugger, Franck Chauvat, Corinne Cassier-Chauvat. The diversity of molecular mechanisms of carbonate biomineralization by bacteria. Discover Materials. 2020; 1 (1):1-20.

Chicago/Turabian Style

Sigrid Görgen; Karim Benzerara; Fériel Skouri-Panet; Muriel Gugger; Franck Chauvat; Corinne Cassier-Chauvat. 2020. "The diversity of molecular mechanisms of carbonate biomineralization by bacteria." Discover Materials 1, no. 1: 1-20.

Journal article
Published: 17 August 2020 in Nature Chemistry
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Cyclic peptide natural products have served as important drug molecules, with several examples used clinically. Enzymatic or chemical macrocyclization is the key transformation for constructing these chemotypes. Methods to generate new and diverse cyclic peptide scaffolds enabling the modular and predictable synthesis of peptide libraries are desirable in drug discovery platforms. Here we identify a suite of post-translational modifying enzymes from bacteria that install single or multiple strained cyclophane macrocycles. The crosslinking occurs on three-residue motifs that include tryptophan or phenylalanine to form indole- or phenyl-bridged cyclophanes. The macrocycles display restricted rotation of the aromatic ring and induce planar chirality in the asymmetric indole bridge. The biosynthetic gene clusters originate from a broad range of bacteria derived from marine, terrestrial and human microbiomes. Three-residue cyclophane-forming enzymes define a new and significant natural product family and occupy a distinct region in sequence–function space.

ACS Style

Thi Quynh Ngoc Nguyen; Yi Wei Tooh; Ryosuke Sugiyama; Mugilarasi Purushothaman; Li Chuan Leow; Karyna Hanif; Rubin How Sheng Yong; Irene Agatha; Fernaldo R. Winnerdy; Muriel Gugger; Anh Tuân Phan; Brandon I. Morinaka. Post-translational formation of strained cyclophanes in bacteria. Nature Chemistry 2020, 12, 1042 -1053.

AMA Style

Thi Quynh Ngoc Nguyen, Yi Wei Tooh, Ryosuke Sugiyama, Mugilarasi Purushothaman, Li Chuan Leow, Karyna Hanif, Rubin How Sheng Yong, Irene Agatha, Fernaldo R. Winnerdy, Muriel Gugger, Anh Tuân Phan, Brandon I. Morinaka. Post-translational formation of strained cyclophanes in bacteria. Nature Chemistry. 2020; 12 (11):1042-1053.

Chicago/Turabian Style

Thi Quynh Ngoc Nguyen; Yi Wei Tooh; Ryosuke Sugiyama; Mugilarasi Purushothaman; Li Chuan Leow; Karyna Hanif; Rubin How Sheng Yong; Irene Agatha; Fernaldo R. Winnerdy; Muriel Gugger; Anh Tuân Phan; Brandon I. Morinaka. 2020. "Post-translational formation of strained cyclophanes in bacteria." Nature Chemistry 12, no. 11: 1042-1053.

Communication
Published: 12 March 2020 in Angewandte Chemie International Edition
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Proteusins are a family of bacterial ribosomal peptides that largely remain hypothetical, genome‐predicted metabolites. The only known members are the polytheonamide‐type cytotoxins with remarkably complex structures due to numerous unusual posttranslational modifications (PTMs). Cyanobacteria contain large numbers of putative proteusin loci with highly variable sets of PTM gene candidates. Interrogating whether this gene diversity offers chemical and pharmacological discovery potential beyond polytheonamide‐type compounds, we characterized landornamide A, the product of the silent osp gene cluster from Kamptonema sp. PCC 6506. Pathway reconstruction in E. coli revealed a peptide combining lanthionines, d‐residues, and, as a novel PTM, two ornithines introduced by the arginase‐like enzyme OspR. Landornamide A inhibited lymphocytic choriomeningitis virus infecting mouse fibrosarcoma cells, representing one of the few known anti‐arenaviral compounds. The data support proteusins as a rich resource of chemical scaffolds, new maturation enzymes, and bioactivities.

ACS Style

Nina M. Bösch; Mariana Borsa; Ute Greczmiel; Brandon I. Morinaka; Muriel Gugger; Annette Oxenius; Anna Lisa Vagstad; Jörn Piel. Landornamides: Antiviral Ornithine‐Containing Ribosomal Peptides Discovered through Genome Mining. Angewandte Chemie International Edition 2020, 59, 11763 -11768.

AMA Style

Nina M. Bösch, Mariana Borsa, Ute Greczmiel, Brandon I. Morinaka, Muriel Gugger, Annette Oxenius, Anna Lisa Vagstad, Jörn Piel. Landornamides: Antiviral Ornithine‐Containing Ribosomal Peptides Discovered through Genome Mining. Angewandte Chemie International Edition. 2020; 59 (29):11763-11768.

Chicago/Turabian Style

Nina M. Bösch; Mariana Borsa; Ute Greczmiel; Brandon I. Morinaka; Muriel Gugger; Annette Oxenius; Anna Lisa Vagstad; Jörn Piel. 2020. "Landornamides: Antiviral Ornithine‐Containing Ribosomal Peptides Discovered through Genome Mining." Angewandte Chemie International Edition 59, no. 29: 11763-11768.

Short communication
Published: 10 January 2020 in Organic Geochemistry
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The heterocyte (heterocyst) glycolipid (HG) content of heterocytous (heterocystous) cyanobacteria can principally be separated into two different types. In the first type, the aglycone moiety attached to the sugar headgroup exclusively contains hydroxyl functionalities resulting in the formation of HG diols and HG triols. In the second type, one of the hydroxyl groups is replaced by a ketone functionality giving rise to HG keto-ols and HG keto-diols. In the N2-fixing heterocytous cyanobacterium Microchaete sp. PCC 7126 both types of HGs were dominant and consisted primarily of two structural isomers each of the HG28 diol and HG28 keto-ol. In addition to these well-characterized HGs, Microchaete sp. PCC 7126 also contained a yet undescribed type of HG that based on comparison of retention times, molecular weight and mass spectrometry consisted of a hexose headgroup attached to an aglycone moiety with 28 carbon atoms at which two instead of one ketone functionalities were attached. Hence, the novel HG structure was identified as HG28 diketone. This study thus provides further evidence for the large structural diversity of HGs, which allows chemotaxonomic profiling of heterocytous cyanobacteria and in turn studying the community composition of these important diazotrophs in the geological rock record.

ACS Style

Thorsten Bauersachs; Muriel Gugger; Lorenz Schwark. Heterocyte glycolipid diketones: A novel type of biomarker in the N2-fixing heterocytous cyanobacterium Microchaete sp. Organic Geochemistry 2020, 141, 103976 .

AMA Style

Thorsten Bauersachs, Muriel Gugger, Lorenz Schwark. Heterocyte glycolipid diketones: A novel type of biomarker in the N2-fixing heterocytous cyanobacterium Microchaete sp. Organic Geochemistry. 2020; 141 ():103976.

Chicago/Turabian Style

Thorsten Bauersachs; Muriel Gugger; Lorenz Schwark. 2020. "Heterocyte glycolipid diketones: A novel type of biomarker in the N2-fixing heterocytous cyanobacterium Microchaete sp." Organic Geochemistry 141, no. : 103976.

Report
Published: 12 December 2019 in Current Biology
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Summary Geosmin is one of the most recognizable and common microbial smells on the planet. Some insects, like mosquitoes, require microbial-rich environments for their progeny, whereas for other insects such microbes may prove dangerous. In the vinegar fly Drosophila melanogaster, geosmin is decoded in a remarkably precise fashion and induces aversion, presumably signaling the presence of harmful microbes [1]. We have here investigated the effect of geosmin on the behavior of the yellow fever mosquito Aedes aegypti. In contrast to flies, geosmin is not aversive but mediates egg-laying site selection. Female mosquitoes likely associate geosmin with microbes, including cyanobacteria consumed by larvae [2], who also find geosmin—as well as geosmin-producing cyanobacteria—attractive. Using in vivo multiphoton calcium imaging from transgenic PUb-GCaMP6s mosquitoes, we show that Ae. aegypti code geosmin in a qualitatively similar fashion to flies, i.e., through a single olfactory channel with a high degree of sensitivity for this volatile. We further demonstrate that geosmin can be used as bait under field conditions, and finally, we show that geosmin, which is both expensive and difficult to obtain, can be substituted by beetroot peel extract, providing a cheap and viable potential mean for mosquito control and surveillance in developing countries.

ACS Style

Nadia Melo; Gabriella H. Wolff; Andre Luis Costa-Da-Silva; Robert Arribas; Merybeth Fernandez Triana; Muriel Gugger; Jeffrey A. Riffell; Matthew DeGennaro; Marcus C. Stensmyr. Geosmin Attracts Aedes aegypti Mosquitoes to Oviposition Sites. Current Biology 2019, 30, 127 -134.e5.

AMA Style

Nadia Melo, Gabriella H. Wolff, Andre Luis Costa-Da-Silva, Robert Arribas, Merybeth Fernandez Triana, Muriel Gugger, Jeffrey A. Riffell, Matthew DeGennaro, Marcus C. Stensmyr. Geosmin Attracts Aedes aegypti Mosquitoes to Oviposition Sites. Current Biology. 2019; 30 (1):127-134.e5.

Chicago/Turabian Style

Nadia Melo; Gabriella H. Wolff; Andre Luis Costa-Da-Silva; Robert Arribas; Merybeth Fernandez Triana; Muriel Gugger; Jeffrey A. Riffell; Matthew DeGennaro; Marcus C. Stensmyr. 2019. "Geosmin Attracts Aedes aegypti Mosquitoes to Oviposition Sites." Current Biology 30, no. 1: 127-134.e5.

Article
Published: 09 December 2019 in Nature Plants
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Photosystem I (PSI) is present as trimeric complexes in most characterized cyanobacteria and as monomers in plants and algae. Recent reports of tetrameric PSI have raised questions regarding its structural basis, physiological role, phylogenetic distribution and evolutionary significance. Here, we examined PSI in 61 cyanobacteria, showing that tetrameric PSI, which correlates with the psaL gene and a distinct genomic structure, is widespread among heterocyst-forming cyanobacteria and their close relatives. Physiological studies revealed that expression of tetrameric PSI is favoured under high light, with an increased content of novel PSI-bound carotenoids (myxoxanthophyll, canthaxanthan and echinenone). In sum, this work suggests that tetrameric PSI is an adaptation to high light intensity, and that change in PsaL leads to monomerization of trimeric PSI, supporting the hypothesis of tetrameric PSI being the evolutionary intermediate in the transition from cyanobacterial trimeric PSI to monomeric PSI in plants and algae.

ACS Style

Meng Li; Alexandra Calteau; Dmitry A. Semchonok; Thomas A. Witt; Jonathan T. Nguyen; Nathalie Sassoon; Egbert J. Boekema; Julian Whitelegge; Muriel Gugger; Barry D. Bruce. Physiological and evolutionary implications of tetrameric photosystem I in cyanobacteria. Nature Plants 2019, 5, 1309 -1319.

AMA Style

Meng Li, Alexandra Calteau, Dmitry A. Semchonok, Thomas A. Witt, Jonathan T. Nguyen, Nathalie Sassoon, Egbert J. Boekema, Julian Whitelegge, Muriel Gugger, Barry D. Bruce. Physiological and evolutionary implications of tetrameric photosystem I in cyanobacteria. Nature Plants. 2019; 5 (12):1309-1319.

Chicago/Turabian Style

Meng Li; Alexandra Calteau; Dmitry A. Semchonok; Thomas A. Witt; Jonathan T. Nguyen; Nathalie Sassoon; Egbert J. Boekema; Julian Whitelegge; Muriel Gugger; Barry D. Bruce. 2019. "Physiological and evolutionary implications of tetrameric photosystem I in cyanobacteria." Nature Plants 5, no. 12: 1309-1319.

Research article
Published: 01 November 2019 in ACS Chemical Biology
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Prenylation is a common step in the biosynthesis of many natural products and plays an important role in increasing their structural diversity and enhancing biological activity. Muscoride A is a linear peptide alkaloid that contain two contiguous oxazoles and unusual prenyl groups that protect the amino and carboxy termini. Here we identified the 12.7 kb muscoride (mus) biosynthetic gene clusters from Nostoc spp. PCC 7906 and UHCC 0398. The mus biosynthetic gene clus-ters encode enzymes for the heterocyclization, oxidation, and prenylation of the MusE precursor protein. The mus gene clusters encodes two copies of the cyanobactin prenyltransfer-ase, MusF1 and MusF2. The predicted tetrapeptide substrate of MusF1 and MusF2 was synthesized through a novel tandem cyclization route in only eight steps. Biochemical assays demonstrated that MusF1 acts on the carboxy-terminus while MusF2 acts on the amino-terminus of the tetrapeptide sub-strate. We show that the MusF2 enzyme catalyzes the reverse or forward prenylation of amino-termini from Nostoc sp. PCC 7906 and UHCC 0398, respectively. This finding expands the regiospecific chemical functionality of cyanobactin prenyl-transferases and the chemical diversity of the cyanobactin family of natural products to include bis-prenylated polyoxa-zole linear peptides.

ACS Style

Antti Mattila; Rose-Marie Andsten; Mikael Jumppanen; Michele Assante; Jouni Jokela; Matti Wahlsten; Kornelia M. Mikula; Cihad Sigindere; Daniel H. Kwak; Muriel Gugger; Harri Koskela; Kaarina Sivonen; Xinyu Liu; Jari Yli-Kauhaluoma; Hideo Iwaï; David P. Fewer. Biosynthesis of the Bis-Prenylated Alkaloids Muscoride A and B. ACS Chemical Biology 2019, 14, 2683 -2690.

AMA Style

Antti Mattila, Rose-Marie Andsten, Mikael Jumppanen, Michele Assante, Jouni Jokela, Matti Wahlsten, Kornelia M. Mikula, Cihad Sigindere, Daniel H. Kwak, Muriel Gugger, Harri Koskela, Kaarina Sivonen, Xinyu Liu, Jari Yli-Kauhaluoma, Hideo Iwaï, David P. Fewer. Biosynthesis of the Bis-Prenylated Alkaloids Muscoride A and B. ACS Chemical Biology. 2019; 14 (12):2683-2690.

Chicago/Turabian Style

Antti Mattila; Rose-Marie Andsten; Mikael Jumppanen; Michele Assante; Jouni Jokela; Matti Wahlsten; Kornelia M. Mikula; Cihad Sigindere; Daniel H. Kwak; Muriel Gugger; Harri Koskela; Kaarina Sivonen; Xinyu Liu; Jari Yli-Kauhaluoma; Hideo Iwaï; David P. Fewer. 2019. "Biosynthesis of the Bis-Prenylated Alkaloids Muscoride A and B." ACS Chemical Biology 14, no. 12: 2683-2690.

Research article
Published: 06 September 2019 in PLOS ONE
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Efficient RNA extraction methods are needed to study transcript regulation. Such methods must lyse the cell without degrading the genetic material. For cyanobacteria this can be particularly challenging because of the presence of the cyanobacteria cell envelope. The great breath of cyanobacterial shape and size (unicellular, colonial, or filamentous multicellular) created a variety of cell lysis methods. However, there is still a lack of reliable techniques for nucleic acid extraction for several types of cyanobacteria. Here we designed and tested 15 extraction methods using physical, thermic or chemical stress on the filamentous cyanobacteria Planktothrix agardhii. Techniques based on the use of beads, sonication, and heat shock appeared to be too soft to break the Planktothrix agardhii cell envelope, whereas techniques based on the use of detergents degraded the cell envelope but also the RNA. Two protocols allowed to successfully obtain good-quality RNA. The first protocol consisted to manually crush the frozen cell pellet with a pestle and the second was based on the use of high-intensity ultra-sonication. When comparing these two, the high-intensity ultra-sonication protocol was less laborious, faster and allowed to extract 3.5 times more RNA compared to the liquid nitrogen pestle protocol. The high-intensity ultra-sonication protocol was then tested on five Planktothrix strains, this protocol allowed to obtain >8.5 μg of RNA for approximatively 3.5 × 108 cells. The extracted RNA were characterized by 260/280 and 260/230 ratio > to 2, indicating that the samples were devoid of contaminant, and RNA Quality Number > to 7, meaning that the integrity of RNA was preserved with this extraction method. In conclusion, the method we developed based on high-intensity ultra-sonication proved its efficacy in the extraction of Planktothrix RNA and could be helpful for other types of samples.

ACS Style

Sandra Kim Tiam; Katia Comte; Caroline Dalle; Charlotte Duval; Claire Pancrace; Muriel Gugger; Benjamin Marie; Claude Yéprémian; Cécile Bernard. Development of a new extraction method based on high-intensity ultra-sonication to study RNA regulation of the filamentous cyanobacteria Planktothrix. PLOS ONE 2019, 14, e0222029 .

AMA Style

Sandra Kim Tiam, Katia Comte, Caroline Dalle, Charlotte Duval, Claire Pancrace, Muriel Gugger, Benjamin Marie, Claude Yéprémian, Cécile Bernard. Development of a new extraction method based on high-intensity ultra-sonication to study RNA regulation of the filamentous cyanobacteria Planktothrix. PLOS ONE. 2019; 14 (9):e0222029.

Chicago/Turabian Style

Sandra Kim Tiam; Katia Comte; Caroline Dalle; Charlotte Duval; Claire Pancrace; Muriel Gugger; Benjamin Marie; Claude Yéprémian; Cécile Bernard. 2019. "Development of a new extraction method based on high-intensity ultra-sonication to study RNA regulation of the filamentous cyanobacteria Planktothrix." PLOS ONE 14, no. 9: e0222029.

Journal article
Published: 27 August 2019 in Toxins
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Cyanobacteria are an ancient lineage of slow-growing photosynthetic bacteria and a prolific source of natural products with diverse chemical structures and potent biological activities and toxicities. The chemical identification of these compounds remains a major bottleneck. Strategies that can prioritize the most prolific strains and novel compounds are of great interest. Here, we combine chemical analysis and genomics to investigate the chemodiversity of secondary metabolites based on their pattern of distribution within some cyanobacteria. Planktothrix being a cyanobacterial genus known to form blooms worldwide and to produce a broad spectrum of toxins and other bioactive compounds, we applied this combined approach on four closely related strains of Planktothrix. The chemical diversity of the metabolites produced by the four strains was evaluated using an untargeted metabolomics strategy with high-resolution LC–MS. Metabolite profiles were correlated with the potential of metabolite production identified by genomics for the different strains. Although, the Planktothrix strains present a global similarity in terms of a biosynthetic cluster gene for microcystin, aeruginosin, and prenylagaramide for example, we found remarkable strain-specific chemodiversity. Only few of the chemical features were common to the four studied strains. Additionally, the MS/MS data were analyzed using Global Natural Products Social Molecular Networking (GNPS) to identify molecular families of the same biosynthetic origin. In conclusion, we depict an efficient, integrative strategy for elucidating the chemical diversity of a given genus and link the data obtained from analytical chemistry to biosynthetic genes of cyanobacteria.

ACS Style

Sandra Kim Tiam; Muriel Gugger; Justine DeMay; Séverine Le Manach; Charlotte Duval; Cécile Bernard; Benjamin Marie. Insights into the Diversity of Secondary Metabolites of Planktothrix Using a Biphasic Approach Combining Global Genomics and Metabolomics. Toxins 2019, 11, 498 .

AMA Style

Sandra Kim Tiam, Muriel Gugger, Justine DeMay, Séverine Le Manach, Charlotte Duval, Cécile Bernard, Benjamin Marie. Insights into the Diversity of Secondary Metabolites of Planktothrix Using a Biphasic Approach Combining Global Genomics and Metabolomics. Toxins. 2019; 11 (9):498.

Chicago/Turabian Style

Sandra Kim Tiam; Muriel Gugger; Justine DeMay; Séverine Le Manach; Charlotte Duval; Cécile Bernard; Benjamin Marie. 2019. "Insights into the Diversity of Secondary Metabolites of Planktothrix Using a Biphasic Approach Combining Global Genomics and Metabolomics." Toxins 11, no. 9: 498.

Journal article
Published: 26 July 2019 in Geobiology
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Several species of cyanobacteria biomineralizing intracellular amorphous calcium carbonates (ACC) were recently discovered. However, the mechanisms involved in this biomineralization process and the determinants discriminating species forming intracellular ACC from those not forming intracellular ACC remain unknown. Recently, it was hypothesized that the intensity of Ca uptake (i.e., how much Ca was scavenged from the extracellular solution) might be a major parameter controlling the capability of a cyanobacterium to form intracellular ACC. Here, we tested this hypothesis by systematically measuring the Ca uptake by a set of 52 cyanobacterial strains cultured in the same growth medium. The results evidenced a dichotomy among cyanobacteria regarding Ca sequestration capabilities, with all strains forming intracellular ACC incorporating significantly more calcium than strains not forming ACC. Moreover, Ca provided at a concentration of 50 μM in BG-11 was shown to be limiting for the growth of some of the strains forming intracellular ACC, suggesting an overlooked quantitative role of Ca for these strains. All cyanobacteria forming intracellular ACC contained at least one gene coding for a mechanosensitive channel, which might be involved in Ca influx, as well as at least one gene coding for a Ca2+ /H+ exchanger and membrane proteins of the UPF0016 family, which might be involved in active Ca transport either from the cytosol to the extracellular solution or the cytosol toward an intracellular compartment. Overall, massive Ca sequestration may have an indirect role by allowing the formation of intracellular ACC. The latter may be beneficial to the growth of the cells as a storage of inorganic C and/or a buffer of intracellular pH. Moreover, high Ca scavenging by cyanobacteria biomineralizing intracellular ACC, a trait shared with endolithic cyanobacteria, suggests that these cyanobacteria should be considered as potentially significant geochemical reservoirs of Ca.

ACS Style

Alexis De Wever; Karim Benzerara; Margot Coutaud; Géraldine Caumes; Mélanie Poinsot; Fériel Skouri‐Panet; Thierry Laurent; Elodie Duprat; Muriel Gugger. Evidence of high Ca uptake by cyanobacteria forming intracellular CaCO3and impact on their growth. Geobiology 2019, 17, 676 -690.

AMA Style

Alexis De Wever, Karim Benzerara, Margot Coutaud, Géraldine Caumes, Mélanie Poinsot, Fériel Skouri‐Panet, Thierry Laurent, Elodie Duprat, Muriel Gugger. Evidence of high Ca uptake by cyanobacteria forming intracellular CaCO3and impact on their growth. Geobiology. 2019; 17 (6):676-690.

Chicago/Turabian Style

Alexis De Wever; Karim Benzerara; Margot Coutaud; Géraldine Caumes; Mélanie Poinsot; Fériel Skouri‐Panet; Thierry Laurent; Elodie Duprat; Muriel Gugger. 2019. "Evidence of high Ca uptake by cyanobacteria forming intracellular CaCO3and impact on their growth." Geobiology 17, no. 6: 676-690.

Journal article
Published: 15 July 2019 in Nature Chemical Biology
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Bacterial trans-acyltransferase polyketide synthases (trans-AT PKSs) are among the most complex known enzymes from secondary metabolism and are responsible for the biosynthesis of highly diverse bioactive polyketides. However, most of these metabolites remain uncharacterized, since trans-AT PKSs frequently occur in poorly studied microbes and feature a remarkable array of non-canonical biosynthetic components with poorly understood functions. As a consequence, genome-guided natural product identification has been challenging. To enable de novo structural predictions for trans-AT PKS-derived polyketides, we developed the trans-AT PKS polyketide predictor (TransATor). TransATor is a versatile bio- and chemoinformatics web application that suggests informative chemical structures for even highly aberrant trans-AT PKS biosynthetic gene clusters, thus permitting hypothesis-based, targeted biotechnological discovery and biosynthetic studies. We demonstrate the applicative scope in several examples, including the characterization of new variants of bioactive natural products as well as structurally new polyketides from unusual bacterial sources. The TransATor application bioinformatically predicts chemical structures for the products of trans-acyltransferase polyketide synthases, enabling the characterization of new polyketide natural products from (unusual) bacterial sources.

ACS Style

Eric Jan Nikolaus Helfrich; Reiko Ueoka; Alon Dolev; Michael Rust; Roy A. Meoded; Agneya Bhushan; Gianmaria Califano; Rodrigo Costa; Muriel Gugger; Christoph Steinbeck; Pablo Moreno; Jörn Piel. Automated structure prediction of trans-acyltransferase polyketide synthase products. Nature Chemical Biology 2019, 15, 813 -821.

AMA Style

Eric Jan Nikolaus Helfrich, Reiko Ueoka, Alon Dolev, Michael Rust, Roy A. Meoded, Agneya Bhushan, Gianmaria Califano, Rodrigo Costa, Muriel Gugger, Christoph Steinbeck, Pablo Moreno, Jörn Piel. Automated structure prediction of trans-acyltransferase polyketide synthase products. Nature Chemical Biology. 2019; 15 (8):813-821.

Chicago/Turabian Style

Eric Jan Nikolaus Helfrich; Reiko Ueoka; Alon Dolev; Michael Rust; Roy A. Meoded; Agneya Bhushan; Gianmaria Califano; Rodrigo Costa; Muriel Gugger; Christoph Steinbeck; Pablo Moreno; Jörn Piel. 2019. "Automated structure prediction of trans-acyltransferase polyketide synthase products." Nature Chemical Biology 15, no. 8: 813-821.

Journal article
Published: 04 July 2019 in Phytochemistry
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The cyanobacterial phylum is currently divided into five subsections (I–V), with the latter two containing no or false-branching (nostocalean) and true-branching (stigonematalean) cyanobacteria. Although morphological traits (such as cellular division and secondary branches) clearly separate both types of heterocytous cyanobacteria, molecular evidence indicates that stigonematalean cyanobacteria (Subsection V) do not form a monophyletic group but instead are interspersed and nested within the nostocalean cyanobacteria (Subsection IV). To further resolve the phylogeny of heterocytous cyanobacteria, we here analyzed the distribution of heterocyte glycolipids (HGs) in the true-branching cyanobacterium Stigonema ocellatum SAG 48.90 (type genus of Subsection V) and compared it with the HG inventory of other stigonematalean and nostocalean cyanobacteria. The most dominant HGs in S. ocellatum SAG 48.90 were 1-(O-hexose)-27-keto-3,25-octacosanediol (HG28 keto-diol) and 1-(O-hexose)-3,25,27-octacosanetriol (HG28 triol), which together constituted ca. 94% of all HGs. In addition, 1-(O-hexose)-3-keto-27-octacosanols (HG28 keto-ols), 1-(O-hexose)-3,27-octacosanediols (HG28 diols), 1-(O-hexose)-3-keto-27,29-triacontanediol (HG30 keto-diol) and 1-(O-hexose)-3,27,29-triacontanetriol (HG30 triol) occurred in minor abundances. Heterocyte glycolipids previously reported to be unique for stigonematalean cyanobacteria, i.e. 1-(O-hexose)-3,29,31-dotriacontanetriols (HG32 triols) and 1-(O-hexose)-3-keto-29,31-dotriacontanediols (HG32 keto-diols), were not detected in S. ocellatum SAG 48.90. Comparison of the HG distribution pattern with those of other heterocytous cyanobacteria indicated that S. ocellatum SAG 48.90 is most closely related to the nostocalean families Rivulariaceae and Scytonemataceae, which is complementary to reconstructed 16S rRNA gene sequence phylogenies. Our HG-based data thus provides evidence for the polyphyly of stigonematalean cyanobacteria, independent from molecular approaches, and points to the need for a critical re-evaluation of the current taxonomy of heterocytous cyanobacteria.

ACS Style

Thorsten Bauersachs; Scott R. Miller; Muriel Gugger; Opayi Mudimu; Thomas Friedl; Lorenz Schwark. Heterocyte glycolipids indicate polyphyly of stigonematalean cyanobacteria. Phytochemistry 2019, 166, 112059 .

AMA Style

Thorsten Bauersachs, Scott R. Miller, Muriel Gugger, Opayi Mudimu, Thomas Friedl, Lorenz Schwark. Heterocyte glycolipids indicate polyphyly of stigonematalean cyanobacteria. Phytochemistry. 2019; 166 ():112059.

Chicago/Turabian Style

Thorsten Bauersachs; Scott R. Miller; Muriel Gugger; Opayi Mudimu; Thomas Friedl; Lorenz Schwark. 2019. "Heterocyte glycolipids indicate polyphyly of stigonematalean cyanobacteria." Phytochemistry 166, no. : 112059.

Journal article
Published: 05 April 2019 in Scientific Reports
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Tunneling nanotubes (TNTs) are actin-containing membrane protrusions that play an essential role in long-range intercellular communication. They are involved in development of various diseases by allowing transfer of pathogens or protein aggregates as well as organelles such as mitochondria. Increase in TNT formation has been linked to many pathological conditions. Here we show that nM concentrations of tolytoxin, a cyanobacterial macrolide that targets actin by inhibition of its polymerization, significantly decrease the number of TNT-connected cells, as well as transfer of mitochondria and α-synuclein fibrils in two different cell lines of neuronal (SH-SY5Y) and epithelial (SW13) origin. As the cytoskeleton of the tested cell remain preserved, this macrolide could serve as a valuable tool for future therapies against diseases propagated by TNTs.

ACS Style

Aysegul Dilsizoglu Senol; Anna Pepe; Clara Grudina; Nathalie Sassoon; Ueoka Reiko; Luc Bousset; Ronald Melki; Jörn Piel; Muriel Gugger; Chiara Zurzolo. Effect of tolytoxin on tunneling nanotube formation and function. Scientific Reports 2019, 9, 1 -15.

AMA Style

Aysegul Dilsizoglu Senol, Anna Pepe, Clara Grudina, Nathalie Sassoon, Ueoka Reiko, Luc Bousset, Ronald Melki, Jörn Piel, Muriel Gugger, Chiara Zurzolo. Effect of tolytoxin on tunneling nanotube formation and function. Scientific Reports. 2019; 9 (1):1-15.

Chicago/Turabian Style

Aysegul Dilsizoglu Senol; Anna Pepe; Clara Grudina; Nathalie Sassoon; Ueoka Reiko; Luc Bousset; Ronald Melki; Jörn Piel; Muriel Gugger; Chiara Zurzolo. 2019. "Effect of tolytoxin on tunneling nanotube formation and function." Scientific Reports 9, no. 1: 1-15.

Preprint
Published: 04 April 2019
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Geosmin is one of the most recognizable and common microbial smells on the planet. Some insects, like mosquitoes, require microbial-rich environments for their progeny, whereas for other insects such microbes may prove dangerous. In the vinegar flyDrosophila melanogaster, geosmin is decoded in a remarkably precise fashion and induces aversion, presumably signaling the presence of harmful microbes. We have here investigated the effect of geosmin on the behavior of the yellow fever mosquitoAedes aegypti. In contrast to flies, geosmin is not aversive in mosquitoes but stimulates egg-laying site selection. Female mosquitoes could associate geosmin with microbes, including cyanobacteria consumed by larvae, who also find geosmin – as well as geosmin producing cyanobacteria – attractive. Usingin vivomultiphoton imaging from mosquitoes with pan-neural expression of the calcium reporter GCaMP6s, we show thatAe. aegypticode geosmin in a similar fashion to flies, i.e. with extreme sensitivity and with a high degree of selectivity. We further demonstrate that geosmin can be used as bait under field conditions, and finally we show that geosmin, which is both expensive and difficult to obtain, can be substituted by beetroot peel extract, providing a cheap and viable mean of mosquito control and surveillance in developing countries.

ACS Style

Nadia Melo; Gabriella H. Wolff; Andre Luis Costa-Da-Silva; Robert Arribas; Merybeth Fernandez Triana; Muriel Gugger; Jeffrey A. Riffell; Matthew DeGennaro; Marcus C. Stensmyr. Geosmin attractsAedes aegyptimosquitoes to oviposition sites. 2019, 598698 .

AMA Style

Nadia Melo, Gabriella H. Wolff, Andre Luis Costa-Da-Silva, Robert Arribas, Merybeth Fernandez Triana, Muriel Gugger, Jeffrey A. Riffell, Matthew DeGennaro, Marcus C. Stensmyr. Geosmin attractsAedes aegyptimosquitoes to oviposition sites. . 2019; ():598698.

Chicago/Turabian Style

Nadia Melo; Gabriella H. Wolff; Andre Luis Costa-Da-Silva; Robert Arribas; Merybeth Fernandez Triana; Muriel Gugger; Jeffrey A. Riffell; Matthew DeGennaro; Marcus C. Stensmyr. 2019. "Geosmin attractsAedes aegyptimosquitoes to oviposition sites." , no. : 598698.

Preprint content
Published: 08 February 2019
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Photosystem I (PSI) were reported as trimeric complexes in most characterized cyanobacteria, yet monomers in plants and algae PSI. Recent reports on tetrameric PSI raised questions regarding its structural basis, physiological role, phylogenetic distribution and evolutionary significance. In this study, by examining PSI in 61 cyanobacteria, we show that tetrameric PSI, correlating with a unique psaL gene and genomic structure, is widespread in the heterocyst-forming cyanobacteria and their close relatives. Physiological studies on these cyanobacteria revealed that tetrameric PSI is favored under high light, with an increased content of novel PSI-bound carotenoids (myxoxanthophyll, canthaxanthan and echinenone). Together this work suggests that tetrameric PSI is an adaptation to high light, along with results showing that change in PsaL leads to trimeric PSI monomerization, supporting the hypothesis of tetrameric PSI being the evolutionary intermediate in the transition from cyanobacterial trimeric PSI to monomeric PSI in plants and algae.

ACS Style

Meng Li; Alexandra Calteau; Dmitry A. Semchonok; Thomas A. Witt; Jonathan T. Nguyen; Nathalie Sassoon; Egbert J. Boekema; Julian Whitelegge; Muriel Gugger; Barry D. Bruce. Physiological and Evolutionary Implications of Tetrameric Photosystem I in Cyanobacteria. 2019, 544353 .

AMA Style

Meng Li, Alexandra Calteau, Dmitry A. Semchonok, Thomas A. Witt, Jonathan T. Nguyen, Nathalie Sassoon, Egbert J. Boekema, Julian Whitelegge, Muriel Gugger, Barry D. Bruce. Physiological and Evolutionary Implications of Tetrameric Photosystem I in Cyanobacteria. . 2019; ():544353.

Chicago/Turabian Style

Meng Li; Alexandra Calteau; Dmitry A. Semchonok; Thomas A. Witt; Jonathan T. Nguyen; Nathalie Sassoon; Egbert J. Boekema; Julian Whitelegge; Muriel Gugger; Barry D. Bruce. 2019. "Physiological and Evolutionary Implications of Tetrameric Photosystem I in Cyanobacteria." , no. : 544353.

Research article
Published: 17 December 2018 in ACS Chemical Biology
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The cyanobacterial genus Microcystis is known to produce an elaborate array of structurally unique and biologically active natural products including hazardous cyanotoxins. Cytotoxic aeruginoguanidines represent a yet unexplored family of peptides featuring a trisubstituted benzene unit and farnesylated arginine derivatives. In this study, we aimed at assigning these compounds to a biosynthetic gene cluster by utilizing biosynthetic attributes deduced from public genomes of Microcystis and the sporadic distribution of the metabolite in axenic strains of the Pasteur Culture Collection of Cyanobacteria. By integrating genome mining with untargeted metabolomics using liquid chromatography with mass spectrometry, we could link aeruginoguanidine (AGD) to a nonribosomal peptide synthetase gene cluster and co-assign a significantly smaller product to this pathway, microguanidine (MGD), previously only reported from two Microcystis blooms. Further, a new intermediate class of compounds named microguanidine amides was uncovered thereby further enlarging this compound family. The comparison of structurally divergent AGDs and MGDs reveals an outstanding versatility of this biosynthetic pathway and provides insights into the assembly of the two compound subfamilies. Strikingly, aeruginoguanidines and microguanidines were found to be as widespread as the hepatotoxic microcystins, but the occurrence of both toxin families appeared to be mutually exclusive.

ACS Style

Claire Pancrace; Keishi Ishida; Enora Briand; Douglas Gatte Pichi; Annika R. Weiz; Arthur Guljamow; Thibault Scalvenzi; Nathalie Sassoon; Christian Hertweck; Elke Dittmann; Muriel Gugger. Unique Biosynthetic Pathway in Bloom-Forming Cyanobacterial Genus Microcystis Jointly Assembles Cytotoxic Aeruginoguanidines and Microguanidines. ACS Chemical Biology 2018, 14, 67 -75.

AMA Style

Claire Pancrace, Keishi Ishida, Enora Briand, Douglas Gatte Pichi, Annika R. Weiz, Arthur Guljamow, Thibault Scalvenzi, Nathalie Sassoon, Christian Hertweck, Elke Dittmann, Muriel Gugger. Unique Biosynthetic Pathway in Bloom-Forming Cyanobacterial Genus Microcystis Jointly Assembles Cytotoxic Aeruginoguanidines and Microguanidines. ACS Chemical Biology. 2018; 14 (1):67-75.

Chicago/Turabian Style

Claire Pancrace; Keishi Ishida; Enora Briand; Douglas Gatte Pichi; Annika R. Weiz; Arthur Guljamow; Thibault Scalvenzi; Nathalie Sassoon; Christian Hertweck; Elke Dittmann; Muriel Gugger. 2018. "Unique Biosynthetic Pathway in Bloom-Forming Cyanobacterial Genus Microcystis Jointly Assembles Cytotoxic Aeruginoguanidines and Microguanidines." ACS Chemical Biology 14, no. 1: 67-75.

Rapid communication
Published: 24 August 2018 in Organic Letters
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An analysis of cyanobacterial genomes revealed an architecturally unique biosynthetic gene cluster with an unusually high number of genes encoding predicted iron(II)/α-ketoglutarate-dependent halogenases. Mass spectrometry-guided identification of the corresponding metabolites yielded the aranazoles, extensively halogenated nonribosomal peptide–polyketide hybrids. Their chlorine-bearing fatty acyl-like moiety is reminiscent of the hyperhalogenated chlorosulfolipids, natural products of unknown enzymatic origin that were previously isolated from eukaryotic algae and mussels.

ACS Style

Philipp Moosmann; Reiko Ueoka; Muriel Gugger; Jörn Piel. Aranazoles: Extensively Chlorinated Nonribosomal Peptide–Polyketide Hybrids from the Cyanobacterium Fischerella sp. PCC 9339. Organic Letters 2018, 20, 5238 -5241.

AMA Style

Philipp Moosmann, Reiko Ueoka, Muriel Gugger, Jörn Piel. Aranazoles: Extensively Chlorinated Nonribosomal Peptide–Polyketide Hybrids from the Cyanobacterium Fischerella sp. PCC 9339. Organic Letters. 2018; 20 (17):5238-5241.

Chicago/Turabian Style

Philipp Moosmann; Reiko Ueoka; Muriel Gugger; Jörn Piel. 2018. "Aranazoles: Extensively Chlorinated Nonribosomal Peptide–Polyketide Hybrids from the Cyanobacterium Fischerella sp. PCC 9339." Organic Letters 20, no. 17: 5238-5241.

Article
Published: 01 July 2018 in Applied and Environmental Microbiology
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Cyanobacteria can synthesize alkanes and alkenes, which are considered to be infrastructure-compatible biofuels. In terms of physiological function, cyanobacterial hydrocarbons are thought to be essential for membrane flexibility for cell division, size, and growth. The genetic basis for the biosynthesis of terminal olefins (1-alkenes) is a modular type I polyketide synthase (PKS) termed olefin synthase (Ols). The modular architectures of Ols and structural characteristics of alkenes have been investigated only in a few species of the small percentage (approximately 10%) of cyanobacteria that harbor putative Ols pathways. In this study, investigations of the domains, modular architectures, and phylogenies of Ols in 28 cyanobacterial strains suggested distinctive pathway evolution. Structural feature analyses revealed 1-alkenes with three carbon chain lengths (C 15 , C 17 , and C 19 ). In addition, the total cellular fatty acid profile revealed the diversity of the carbon chain lengths, while the fatty acid feeding assay indicated substrate carbon chain length specificity of cyanobacterial Ols enzymes. Finally, in silico analyses suggested that the N terminus of the modular Ols enzyme exhibited characteristics typical of a fatty acyl-adenylate ligase (FAAL), suggesting a mechanism of fatty acid activation via the formation of acyl-adenylates. Our results shed new light on the diversity of cyanobacterial terminal olefins and a mechanism for substrate activation in the biosynthesis of these olefins. IMPORTANCE Cyanobacterial terminal olefins are hydrocarbons with promising applications as advanced biofuels. Despite the basic understanding of the genetic basis of olefin biosynthesis, the structural diversity and phylogeny of the key modular olefin synthase (Ols) have been poorly explored. An overview of the chemical structural traits of terminal olefins in cyanobacteria is provided in this study. In addition, we demonstrated by in vivo fatty acid feeding assays that cyanobacterial Ols enzymes might exhibit substrate carbon chain length specificity. Furthermore, by performing bioinformatic analyses, we observed that the substrate activation domain of Ols exhibited features typical of a fatty acyl-adenylate ligase (FAAL), which activates fatty acids by converting them to fatty acyl-adenylates. Our results provide further insight into the chemical structures of terminal olefins and further elucidate the mechanism of substrate activation for terminal olefin biosynthesis in cyanobacteria.

ACS Style

Tao Zhu; Thibault Scalvenzi; Nathalie Sassoon; Xuefeng Lu; Muriel Gugger. Terminal Olefin Profiles and Phylogenetic Analyses of Olefin Synthases of Diverse Cyanobacterial Species. Applied and Environmental Microbiology 2018, 84, e00425-18 .

AMA Style

Tao Zhu, Thibault Scalvenzi, Nathalie Sassoon, Xuefeng Lu, Muriel Gugger. Terminal Olefin Profiles and Phylogenetic Analyses of Olefin Synthases of Diverse Cyanobacterial Species. Applied and Environmental Microbiology. 2018; 84 (13):e00425-18.

Chicago/Turabian Style

Tao Zhu; Thibault Scalvenzi; Nathalie Sassoon; Xuefeng Lu; Muriel Gugger. 2018. "Terminal Olefin Profiles and Phylogenetic Analyses of Olefin Synthases of Diverse Cyanobacterial Species." Applied and Environmental Microbiology 84, no. 13: e00425-18.