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Papers In Press, published online ahead of print January 23, 2002
J. Biol. Chem, 10.1074/jbc.M111738200
Submitted on December 10, 2001
Revised on January 22, 2002
Accepted on January 23, 2002

The biosynthesis of the aromatic myxobacterial electron transport inhibitor stigmatellin is directed by a novel type of modular polyketide synthase

Nikolaos Gaitatzis, Barbara Silakowski, Brigitte Kunze, Gabriele Nordsiek, Helmut Blöcker, Gerhard Höfle, and Rolf Müller

NBI/MX, GBF, Braunschweig 38124

Corresponding Author: rom{at}gbf.de

Deductions from the molecular analysis of the 65000 bp stigmatellin biosynthetic gene cluster are reported. The biosynthetic genes (stiA-J) encode an unusual bacterial modular type I polyketide synthase (PKS) responsible for the formation of this aromatic electron transport inhibitor produced by the myxobacterium Stigmatella aurantiaca. Involvement of the PKS gene cluster in stigmatellin biosynthesis is shown using site directed mutagenesis. One module of the PKS is assumed to be used iteratively during the biosynthetic process, which seems to involve an unusual transacylation of the biosynthetic intermediate from an acyl carrier protein domain back to the preceding ketosynthase domain. Finally, the polyketide chain is cyclised and aromatised, presumably catalysed by a novel C-terminal domain in StiJ that does not resemble thioesterases. Presented results of feeding experiments are in good agreement with the proposed biosynthetic scheme. In contrast to all other PKS type I systems reported to date, each module of StiA-J is encoded on a separate gene. The gene cluster contains a "stand alone" O-methyl transferase and two unusual O-methyl transferase domains embedded in the PKS. In addition, inactivation of a cytochrome P450-monooxygenase encoding gene involved in post PKS hydroxylation of the aromatic ring leads to the formation of two novel stigmatellin derivatives.


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