title: A Unique Tryptophan C-Prenyltransferase from the Kawaguchipeptin Biosynthetic Pathway.
abstract: 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.
authors: Microbiology and Biotechnology Division, Department of Food and Environmental Sciences, P.O.Box 56, Viikki Biocenter, Viikinkaari 9, 00014, University of Helsinki, Finland.
authors: Anirudra
authors: A
authors: Parajuli
authors: Department of Chemistry, University of Pittsburgh, 219 Parkman Avenue, Pittsburgh, PA, 15260, USA.
authors: Daniel H
authors: DH
authors: Kwak
authors: Marine Biodiscovery Centre, Department of Chemistry, University of Aberdeen, Meston Walk, Aberdeen, AB24 3UE, UK.|Institute of Medical Sciences, University of Aberdeen, Aberdeen, AB25 2ZD, UK.
authors: Luca
authors: L
authors: Dalponte
authors: Microbiology and Biotechnology Division, Department of Food and Environmental Sciences, P.O.Box 56, Viikki Biocenter, Viikinkaari 9, 00014, University of Helsinki, Finland.
authors: Niina
authors: N
authors: Leikoski
authors: Microbiology and Biotechnology Division, Department of Food and Environmental Sciences, P.O.Box 56, Viikki Biocenter, Viikinkaari 9, 00014, University of Helsinki, Finland.|Institute of Microbiology AS CR, v.v.i., Center ALGATECH, Třeboň, Czech Republic.|University of South Bohemia, Faculty of Science, Department of Ecosystem Biology, České Budějovice, Czech Republic.
authors: Tomas
authors: T
authors: Galica
authors: Marine Biodiscovery Centre, Department of Chemistry, University of Aberdeen, Meston Walk, Aberdeen, AB24 3UE, UK.
authors: Ugochukwu
authors: U
authors: Umeobika
authors: Marine Biodiscovery Centre, Department of Chemistry, University of Aberdeen, Meston Walk, Aberdeen, AB24 3UE, UK.
authors: Laurent
authors: L
authors: Trembleau
authors: Biomedical Sciences Research Complex, University of St Andrews, North Haugh, St Andrews, Fife, KY16 9ST, UK.
authors: Andrew
authors: A
authors: Bent
authors: Microbiology and Biotechnology Division, Department of Food and Environmental Sciences, P.O.Box 56, Viikki Biocenter, Viikinkaari 9, 00014, University of Helsinki, Finland.
authors: Kaarina
authors: K
authors: Sivonen
authors: Microbiology and Biotechnology Division, Department of Food and Environmental Sciences, P.O.Box 56, Viikki Biocenter, Viikinkaari 9, 00014, University of Helsinki, Finland.
authors: Matti
authors: M
authors: Wahlsten
authors: Microbiology and Biotechnology Division, Department of Food and Environmental Sciences, P.O.Box 56, Viikki Biocenter, Viikinkaari 9, 00014, University of Helsinki, Finland.
authors: Hao
authors: H
authors: Wang
authors: Institute for Biomedical Technologies (ITB), National Research Council (CNR), via F.lli Cervi 93, Segrate (MI), Italy.
authors: Ermanno
authors: E
authors: Rizzi
authors: Institute for Biomedical Technologies (ITB), National Research Council (CNR), via F.lli Cervi 93, Segrate (MI), Italy.
authors: Gianluca
authors: G
authors: De Bellis
authors: Biomedical Sciences Research Complex, University of St Andrews, North Haugh, St Andrews, Fife, KY16 9ST, UK.
authors: James
authors: J
authors: Naismith
authors: Marine Biodiscovery Centre, Department of Chemistry, University of Aberdeen, Meston Walk, Aberdeen, AB24 3UE, UK.
authors: Marcel
authors: M
authors: Jaspars
authors: Department of Chemistry, University of Pittsburgh, 219 Parkman Avenue, Pittsburgh, PA, 15260, USA. xinyuliu@pitt.edu.
authors: Xinyu
authors: X
authors: Liu
authors: Marine Biodiscovery Centre, Department of Chemistry, University of Aberdeen, Meston Walk, Aberdeen, AB24 3UE, UK. w.houssen@abdn.ac.uk.|Institute of Medical Sciences, University of Aberdeen, Aberdeen, AB25 2ZD, UK. w.houssen@abdn.ac.uk.|Pharmacognosy Department, Faculty of Pharmacy, Mansoura University, Mansoura, 35516, Egypt. w.houssen@abdn.ac.uk.
authors: Wael
authors: W
authors: Houssen
authors: Microbiology and Biotechnology Division, Department of Food and Environmental Sciences, P.O.Box 56, Viikki Biocenter, Viikinkaari 9, 00014, University of Helsinki, Finland. david.fewer@helsinki.fi.
authors: David Peter
authors: DP
authors: Fewer
mesh_terms: D000595:Amino Acid Sequence; D004122:Dimethylallyltranstransferase / Q000737:chemistry / Q000378:metabolism*; D004926:Escherichia coli / Q000235:genetics; D016680:Genome, Bacterial; D046931:Microcystis / Q000235:genetics; D005810:Multigene Family; D014364:Tryptophan / Q000378:metabolism*
chemical_list: D014364:Tryptophan; D004122:Dimethylallyltranstransferase
keywords: biosynthesis; cyanobactins; peptides; prenylation; prenyltransferases