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Molecular mechanism of polyketide shortening in anthraquinone biosynthesis of Photorhabdus luminescens

Abstract

Anthraquinones, a widely distributed class of aromatic natural products, are produced by a type II polyketide synthase system in the Gram-negative bacterium Photorhabdus luminescens. Heterologous expression of the antABCDEFGHI anthraquinone biosynthetic gene cluster in Escherichia coli identified AntI as an unusual lyase, catalysing terminal polyketide shortening prior to formation of the third aromatic ring. Functional in vitro and in vivo analysis of AntI using X-ray crystallography, structure-based mutagenesis, and molecular simulations revealed that AntI converts a defined octaketide to the tricyclic anthraquinone ring via retro-Claisen and Dieckmann reactions. Thus, AntI catalyses a so far unobserved multistep reaction in this PKS system.

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Publication details

The article was received on 13 Feb 2019, accepted on 08 May 2019 and first published on 14 May 2019


Article type: Edge Article
DOI: 10.1039/C9SC00749K
Chem. Sci., 2019, Accepted Manuscript
  • Open access: Creative Commons BY-NC license
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    Molecular mechanism of polyketide shortening in anthraquinone biosynthesis of Photorhabdus luminescens

    Q. Zhou, A. Bräuer, H. Adihou, M. Schmalhofer, P. Saura, G. Grammbitter, V. R. Kaila, M. Groll and H. Bode, Chem. Sci., 2019, Accepted Manuscript , DOI: 10.1039/C9SC00749K

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