4.8 Article

Aranazoles: Extensively Chlorinated Nonribosomal Peptide-Polyketide Hybrids from the Cyanobacterium Fischerella sp PCC 9339

Journal

ORGANIC LETTERS
Volume 20, Issue 17, Pages 5238-5241

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.8b02193

Keywords

-

Funding

  1. SNF [IZLSZ3_149025]
  2. Helmut Horten Foundation
  3. Alexander von Humboldt postdoctoral fellowship
  4. Institut Pasteur

Ask authors/readers for more resources

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

Authors

I am an author on this paper
Click your name to claim this paper and add it to your profile.

Reviews

Primary Rating

4.8
Not enough ratings

Secondary Ratings

Novelty
-
Significance
-
Scientific rigor
-
Rate this paper

Recommended

Article Biochemistry & Molecular Biology

Unique Biosynthetic Pathway in Bloom-Forming Cyanobacterial Genus Microcystis Jointly Assembles Cytotoxic Aeruginoguanidines and Microguanidines

Claire Pancrace, Keishi Ishida, Enora Briand, Douglas Gatte Pichi, Annika R. Weiz, Arthur Guljarnow, Thibault Scalvenzi, Nathalie Sassoon, Christian Hertweck, Elke Dittmann, Muriel Gugger

ACS CHEMICAL BIOLOGY (2019)

Article Biology

Evidence of high Ca uptake by cyanobacteria forming intracellular CaCO3 and impact on their growth

Alexis De Wever, Karim Benzerara, Margot Coutaud, Geraldine Caumes, Melanie Poinsot, Feriel Skouri-Panet, Thierry Laurent, Elodie Duprat, Muriel Gugger

GEOBIOLOGY (2019)

Article Biochemistry & Molecular Biology

Automated structure prediction of trans-acyltransferase polyketide synthase products

Eric J. N. Helfrich, Reiko Ueoka, Alon Dolev, Michael Rust, Roy A. Meodedl, Agneya Bhushan, Gianmaria Califano, Rodrigo Costa, Muriel Gugger, Christoph Steinbeck, Pablo Moreno, Jorn Piel

NATURE CHEMICAL BIOLOGY (2019)

Article Multidisciplinary Sciences

Effect of tolytoxin on tunneling nanotube formation and function

Aysegul Dilsizoglu Senol, Anna Repe, Clara Grudina, Nathalie Sassoon, Ueoka Reiko, Luc Bousset, Ronald Melki, Joern Pie, Muriel Guggert, Chiara Zurzolo

SCIENTIFIC REPORTS (2019)

Article Multidisciplinary Sciences

Development of a new extraction method based on high-intensity ultra-sonication to study RNA regulation of the filamentous cyanobacteria Planktothrix

Sandra Kim Tiam, Katia Comte, Caroline Dalle, Charlotte Duval, Claire Pancrace, Muriel Gugger, Benjamin Marie, Claude Yepremian, Cecile Bernard

PLOS ONE (2019)

Article Food Science & Technology

Insights into the Diversity of Secondary Metabolites of Planktothrix Using a Biphasic Approach Combining Global Genomics and Metabolomics

Sandra Kim Tiam, Muriel Gugger, Justine Demay, Severine Le Manach, Charlotte Duval, Cecile Bernard, Benjamin Marie

TOXINS (2019)

Article Biochemistry & Molecular Biology

Biosynthesis of the Bis-Prenylated Alkaloids Muscoride A and B

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 Iwai, David P. Fewer

ACS CHEMICAL BIOLOGY (2019)

Article Biochemistry & Molecular Biology

Heterocyte glycolipids indicate polyphyly of stigonematalean cyanobacteria

Thorsten Bauersachs, Scott R. Miller, Muriel Gugger, Opayi Mudimu, Thomas Friedl, Lorenz Schwark

PHYTOCHEMISTRY (2019)

Article Biochemistry & Molecular Biology

Geosmin Attracts Aedes aegypti Mosquitoes to Oviposition Sites

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

CURRENT BIOLOGY (2020)

Article Chemistry, Multidisciplinary

Landornamides: Antiviral Ornithine-Containing Ribosomal Peptides Discovered through Genome Mining

Nina M. Bosch, Mariana Borsa, Ute Greczmiel, Brandon I. Morinaka, Muriel Gugger, Annette Oxenius, Anna L. Vagstad, Jorn Piel

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2020)

Article Chemistry, Multidisciplinary

A monodomain class II terpene cyclase assembles complex isoprenoid scaffolds

Philipp Moosmann, Felix Ecker, Stefan Leopold-Messer, Jackson K. B. Cahn, Cora L. Dieterich, Michael Groll, Joern Piel

NATURE CHEMISTRY (2020)

Article Microbiology

Comparative Genomics Discloses the Uniqueness and the Biosynthetic Potential of the Marine CyanobacteriumHyella patelloides

Angela Brito, Jorge Vieira, Cristina P. Vieira, Tao Zhu, Pedro N. Leao, Vitor Ramos, Xuefeng Lu, Vitor M. Vasconcelos, Muriel Gugger, Paula Tamagnini

FRONTIERS IN MICROBIOLOGY (2020)

Article Chemistry, Multidisciplinary

Post-translational formation of strained cyclophanes in bacteria

Thi Quynh Ngoc Nguyen, Yi Wei Tooh, Ryosuke Sugiyama, Thi Phuong Diep Nguyen, Mugilarasi Purushothaman, Li Chuan Leow, Karyna Hanif, Rubin How Sheng Yong, Irene Agatha, Fernaldo R. Winnerdy, Muriel Gugger, Anh Tuan Phan, Brandon Morinaka

NATURE CHEMISTRY (2020)

Article Plant Sciences

Physiological and evolutionary implications of tetrameric photosystem I in cyanobacteria

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

NATURE PLANTS (2019)

No Data Available