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

Organic Letters
Philipp MoosmannJörn Piel

Abstract

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.

References

Apr 13, 1979·Science·J H CardellinaR E Moore
Mar 1, 1969·Proceedings of the National Academy of Sciences of the United States of America·J Elovson, P R Vagelos
Jun 30, 2001·Journal of Natural Products·J I Jiménez, P J Scheuer
Mar 22, 2002·Nature·David O'HaganCormac D Murphy
Oct 31, 2002·Journal of the American Chemical Society·Patrizia CiminielloRoberto Poletti
Jul 10, 2003·Chembiochem : a European Journal of Chemical Biology·Patrick Caffrey
Feb 7, 2004·Nature·Changjiang DongJames H Naismith
Mar 25, 2004·Natural Product Reports·Alison Butler, Jayme N Carter-Franklin
Mar 2, 2005·Journal of Biological Inorganic Chemistry : JBIC : a Publication of the Society of Biological Inorganic Chemistry·Kevin D KoehntopLawrence Que
Mar 23, 2006·Journal of the American Chemical Society·Danica P GalonićChristopher T Walsh
Feb 23, 2008·Chemistry & Biology·Christopher S NeumannChristopher T Walsh
May 12, 2011·Nucleic Acids Research·Marc RöttigOliver Kohlbacher
Jul 5, 2011·International Journal of Systematic and Evolutionary Microbiology·Niclas EngeneWilliam H Gerwick
Jun 30, 2014·Nature Chemical Biology·Vinayak AgarwalBradley S Moore
Jun 28, 2016·Nature Chemical Biology·Andrew J MitchellAmie K Boal

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Citations

Feb 7, 2020·Natural Product Reports·Anthony R CarrollMichèle R Prinsep

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