Cyanobactins are a rapidly growing family of linear and cyclic peptides produced by cyanobacteria. Kawaguchipeptins A and B, two macrocyclic undecapeptides reported earlier from Microcystis aeruginosa NIES-88, are shown to be products of the cyanobactin biosynthetic pathway. The 9 kb kawaguchipeptin (kgp) gene cluster was identified in a 5.26 Mb draft genome of Microcystis aeruginosa NIES-88. We verified that this gene cluster is responsible for the production of the kawaguchipeptins through heterologous expression of the kgp gene cluster in Escherichia coli. The KgpF prenyltransferase was overexpressed and was shown to prenylate C-3 of Trp residues in both linear and cyclic peptides in vitro. Our findings serve to further enhance the structural diversity of cyanobactins to include tryptophan-prenylated cyclic peptides.

Biomedical Sciences Research Complex University of St Andrews North Haugh St Andrews Fife KY16 9ST UK

Department of Chemistry University of Pittsburgh 219 Parkman Avenue Pittsburgh PA 15260 USA

Institute for Biomedical Technologies Italy

Institute of Medical Sciences University of Aberdeen Aberdeen AB25 2ZD UK

Institute of Microbiology AS CR v v i Center ALGATECH Třeboň Czech Republic

Marine Biodiscovery Centre Department of Chemistry University of Aberdeen Meston Walk Aberdeen AB24 3UE UK

Microbiology and Biotechnology Division Department of Food and Environmental Sciences P O Box 56 Viikki Biocenter Viikinkaari 9 00014 University of Helsinki Finland

Pharmacognosy Department Faculty of Pharmacy Mansoura University Mansoura 35516 Egypt

University of South Bohemia Faculty of Science Department of Ecosystem Biology České Budějovice Czech Republic

Angew Chem Int Ed Engl. 2017 Jan 9;56(2):433. doi: 10.1002/anie.201609949. PubMed

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