Issue 1, 2010
From the journal:

Organic & Biomolecular Chemistry

Identification and biosynthesis of tropone derivatives and sulfur volatiles produced by bacteria of the marine Roseobacter clade†

Verena Thiel,a   Thorsten Brinkhoff,b   Jeroen S. Dickschat,a   Susanne Wickel,a   Jörg Grunenberg,a   Irene Wagner-Döbler,c   Meinhard Simonb  and  Stefan Schulz*a  

* Corresponding authors

a Institut für Organische Chemie, Technische Universität Braunschweig, Hagenring 30, 38106 Braunschweig, Germany
E-mail: stefan.schulz@tu-bs.de
Fax: +49-531-391-5272
Tel: +49-531-391-5271

b Institut für Chemie und Biologie des Meeres, Universität Oldenburg, Carl-von-Ossietzky-Str. 9-11, 26111 Oldenburg, Germany

c Helmholtz-Zentrum für Infektionsforschung, Inhoffenstr. 7, 38124 Braunschweig, Germany

Abstract

Bacteria of the Roseobacter clade are abundant marine bacteria and are important contributors to the global sulfur cycle. The volatiles produced by two of its members, Phaeobacter gallaeciensis and Oceanibulbus indolifex, were analyzed to investigate whether the released compounds are derived from sulfur metabolism, and which biosynthetic pathways are involved in their formation. Both bacteria emitted different sulfides and thioesters, including new natural compounds such as S-methyl phenylethanethioate (16) and butyl methanesulfonate (21). The S-methyl alkanoates were identified by comparison with standards that were synthesized from the respective methyl alkanoates by a new method using an easily prepared aluminium/sulfur reagent. Phaeobacter gallaeciensis is also able to produce tropone (37) in large amounts. Its biosynthesis was investigated by various feeding experiments, showing that 37 is formed via a deviation of the phenylacetate catabolism. The unstable tropone hydrate 42 was identified as an intermediate of the tropone biosynthesis that was also released together with tropolone (38).

Graphical abstract: Identification and biosynthesis of tropone derivatives and sulfur volatiles produced by bacteria of the marine Roseobacter clade

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Article information

DOI
https://doi.org/10.1039/B909133E
Article type
Paper
Submitted
08 May 2009
Accepted
30 Sep 2009
First published
12 Nov 2009

Org. Biomol. Chem., 2010,8, 234-246

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Identification and biosynthesis of tropone derivatives and sulfur volatiles produced by bacteria of the marine Roseobacter clade

V. Thiel, T. Brinkhoff, J. S. Dickschat, S. Wickel, J. Grunenberg, I. Wagner-Döbler, M. Simon and S. Schulz, Org. Biomol. Chem., 2010, 8, 234 DOI: 10.1039/B909133E

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