A Unique Tryptophan C-Prenyltransferase from the Kawaguchipeptin Biosynthetic Pathway

Anirudra Parajuli, Daniel H. Kwak, Luca Dalponte, Niina Leikoski, Tomas Galica, Ugochukwu Umeobika, Laurent Trembleau, Andrew Bent, Kaarina Sivonen, Matti Wahlsten, Hao Wang, Ermano Rizzi, Gianluca De Bellis, James Naismith, Marcel Jaspars, Xinyu Liu, Wael Houssen, David Peter Fewer

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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.
Original languageEnglish
Pages (from-to)3660-3663
Number of pages4
JournalAngewandte Chemie
Volume128
Issue number11
Early online date5 Feb 2016
DOIs
Publication statusPublished - 7 Mar 2016

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Genes
Escherichia coli
Biosynthetic Pathways
Cyclic Peptides

Keywords

  • biosynthesis
  • cyanobactins
  • peptides
  • prenylation
  • prenyltransferases

Cite this

Parajuli, A., Kwak, D. H., Dalponte, L., Leikoski, N., Galica, T., Umeobika, U., ... Fewer, D. P. (2016). A Unique Tryptophan C-Prenyltransferase from the Kawaguchipeptin Biosynthetic Pathway. Angewandte Chemie, 128(11), 3660-3663. https://doi.org/10.1002/ange.201509920

A Unique Tryptophan C-Prenyltransferase from the Kawaguchipeptin Biosynthetic Pathway. / Parajuli, Anirudra; Kwak, Daniel H.; Dalponte, Luca; Leikoski, Niina; Galica, Tomas; Umeobika, Ugochukwu; Trembleau, Laurent; Bent, Andrew; Sivonen, Kaarina; Wahlsten, Matti; Wang, Hao; Rizzi, Ermano; De Bellis, Gianluca; Naismith, James; Jaspars, Marcel; Liu, Xinyu; Houssen, Wael; Fewer, David Peter.

In: Angewandte Chemie, Vol. 128, No. 11, 07.03.2016, p. 3660-3663.

Research output: Contribution to journalArticle

Parajuli, A, Kwak, DH, Dalponte, L, Leikoski, N, Galica, T, Umeobika, U, Trembleau, L, Bent, A, Sivonen, K, Wahlsten, M, Wang, H, Rizzi, E, De Bellis, G, Naismith, J, Jaspars, M, Liu, X, Houssen, W & Fewer, DP 2016, 'A Unique Tryptophan C-Prenyltransferase from the Kawaguchipeptin Biosynthetic Pathway' Angewandte Chemie, vol. 128, no. 11, pp. 3660-3663. https://doi.org/10.1002/ange.201509920
Parajuli A, Kwak DH, Dalponte L, Leikoski N, Galica T, Umeobika U et al. A Unique Tryptophan C-Prenyltransferase from the Kawaguchipeptin Biosynthetic Pathway. Angewandte Chemie. 2016 Mar 7;128(11):3660-3663. https://doi.org/10.1002/ange.201509920
Parajuli, Anirudra ; Kwak, Daniel H. ; Dalponte, Luca ; Leikoski, Niina ; Galica, Tomas ; Umeobika, Ugochukwu ; Trembleau, Laurent ; Bent, Andrew ; Sivonen, Kaarina ; Wahlsten, Matti ; Wang, Hao ; Rizzi, Ermano ; De Bellis, Gianluca ; Naismith, James ; Jaspars, Marcel ; Liu, Xinyu ; Houssen, Wael ; Fewer, David Peter. / A Unique Tryptophan C-Prenyltransferase from the Kawaguchipeptin Biosynthetic Pathway. In: Angewandte Chemie. 2016 ; Vol. 128, No. 11. pp. 3660-3663.
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AU - Wang, Hao

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AU - De Bellis, Gianluca

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N1 - Acknowledgements This work was supported by funding of the Academy of Finland (259505), Helsinki University Research grant (490085) and ESCMID grant (4720572) to D.P.F., University of Pittsburgh Central Research Development Fund to X.L., Technology Strategy Board grant (131181) to W.H., M.J. and J.H.N. National Programme of Sustainability I of the Ministry of Education of the Czech Republic I grant (LO1416) to T.G.

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N2 - 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.

AB - 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.

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