A unique Tryptophan C-prenyltransferase from the kawaguchipeptin biosynthetic pathway
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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.
Parajuli , A , Kwak , D H , 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 , D P 2016 , ' A unique Tryptophan C-prenyltransferase from the kawaguchipeptin biosynthetic pathway ' Angewandte Chemie International Edition , vol. 55 , no. 11 , pp. 3596-3599 . DOI: 10.1002/anie.201509920
Angewandte Chemie International Edition
© 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim. This work is made available online in accordance with the publisher’s policies. This is the author created, accepted version manuscript following peer review and may differ slightly from the final published version. The final published version of this work is available at https://dx.doi.org/10.1002/anie.201509920
DescriptionThis 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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