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Issue 25, 2019
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Molecular mechanism of polyketide shortening in anthraquinone biosynthesis of Photorhabdus luminescens

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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.

Graphical abstract: Molecular mechanism of polyketide shortening in anthraquinone biosynthesis of Photorhabdus luminescens

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Article information


Submitted
13 Feb 2019
Accepted
08 May 2019
First published
14 May 2019

This article is Open Access
All publication charges for this article have been paid for by the Royal Society of Chemistry

Chem. Sci., 2019,10, 6341-6349
Article type
Edge Article

Molecular mechanism of polyketide shortening in anthraquinone biosynthesis of Photorhabdus luminescens

Q. Zhou, A. Bräuer, H. Adihou, M. Schmalhofer, P. Saura, G. L. C. Grammbitter, V. R. I. Kaila, M. Groll and H. B. Bode, Chem. Sci., 2019, 10, 6341
DOI: 10.1039/C9SC00749K

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    [Original citation] - Published by The Royal Society of Chemistry.

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