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J. Biol. Chem., Vol. 282, Issue 49, 35546-35553, December 7, 2007

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Pseudomonas fluorescens CHA0 Produces Enantio-pyochelin, the Optical Antipode of the Pseudomonas aeruginosa Siderophore Pyochelin^*

Zeb A. Youard, Gaëtan L. A. Mislin, Paul A. Majcherczyk, Isabelle J. Schalk, and Cornelia Reimmann¹

From the Département de Microbiologie Fondamentale, Université de Lausanne, Bâtiment Biophore, Quartier UNIL-Sorge, CH-1015 Lausanne, Suisse and the Métaux et Microorganismes: Chimie, Biologie et Applications, UMR7175-LC1 CNRS-Université Louis Pasteur, ESBS, Boulevard Sébastien Brant, F-67400 Illkirch, France

The siderophore pyochelin is made by a thiotemplate mechanism from salicylate and two molecules of cysteine. In Pseudomonas aeruginosa, the first cysteine residue is converted to its D-isoform during thiazoline ring formation whereas the second cysteine remains in its L-configuration, thus determining the stereochemistry of the two interconvertible pyochelin diastereoisomers as 4 'R, 2 ''R, 4 ''R (pyochelin I) and 4 'R, 2 ''S, 4 ''R (pyochelin II). Pseudomonas fluorescens CHA0 was found to make a different stereoisomeric mixture, which promoted growth under iron limitation in strain CHA0 and induced the expression of its biosynthetic genes, but was not recognized as a siderophore and signaling molecule by P. aeruginosa. Reciprocally, pyochelin promoted growth and induced pyochelin gene expression in P. aeruginosa, but was not functional in P. fluorescens. The structure of the CHA0 siderophore was determined by mass spectrometry, thin-layer chromatography, NMR, polarimetry, and chiral HPLC as enantio-pyochelin, the optical antipode of the P. aeruginosa siderophore pyochelin. Enantio-pyochelin was chemically synthesized and confirmed to be active in CHA0. Its potential biosynthetic pathway in CHA0 is discussed.

Received for publication, August 22, 2007 , and in revised form, October 11, 2007.

^* This work was supported by the Swiss National Science Foundation for Scientific Research (Project 31-113955/1), the Centre National de la Recherche Scientifique (CNRS), the association Vaincre la Mucoviscidose, and the Agence Nationale de Recherche (Grant ANR-05-JCJC-0181-01). The costs of publication of this article were defrayed in part by the payment of page charges. This article must therefore be hereby marked "advertisement"in accordance with 18 U.S.C. Section 1734 solely to indicate this fact.

The on-line version of this article (available at http://www.jbc.org) contains supplemental Fig. S1.

¹ To whom correspondence should be addressed: Département de Microbiologie Fondamentale, Université de Lausanne, Bâtiment Biophore, Quartier UNIL-Sorge, CH-1015 Lausanne, Suisse. Tel.: 41-21-692-56-32; Fax: 41-21-692-56-35; E-mail: Cornelia.Reimmann{at}unil.ch.

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