Document Detail

Identification and biosynthesis of tropone derivatives and sulfur volatiles produced by bacteria of the marine Roseobacter clade.
MedLine Citation:
PMID:  20024154     Owner:  NLM     Status:  MEDLINE    
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).
Verena Thiel; Thorsten Brinkhoff; Jeroen S Dickschat; Susanne Wickel; J?rg Grunenberg; Irene Wagner-D?bler; Meinhard Simon; Stefan Schulz
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Publication Detail:
Type:  Journal Article; Research Support, Non-U.S. Gov't     Date:  2009-11-12
Journal Detail:
Title:  Organic & biomolecular chemistry     Volume:  8     ISSN:  1477-0539     ISO Abbreviation:  Org. Biomol. Chem.     Publication Date:  2010 Jan 
Date Detail:
Created Date:  2009-12-23     Completed Date:  2010-03-23     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  101154995     Medline TA:  Org Biomol Chem     Country:  England    
Other Details:
Languages:  eng     Pagination:  234-46     Citation Subset:  IM    
Institut f?r Organische Chemie, Technische Universit?t Braunschweig, Hagenring 30, 38106 Braunschweig, Germany.
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MeSH Terms
Molecular Structure
Roseobacter / chemistry,  metabolism*
Sulfur Compounds / analysis*,  metabolism
Tropolone / analogs & derivatives*,  analysis*,  metabolism
Reg. No./Substance:
0/Sulfur Compounds; 533-75-5/Tropolone

From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine

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