Document Detail

The biosynthesis of the aroma volatile 2-methyltetrahydrothiophen-3-one in the bacterium Chitinophaga Fx7914.
MedLine Citation:
PMID:  20680979     Owner:  NLM     Status:  MEDLINE    
2-Methyltetrahydrothiophen-3-one (3) is a volatile compound that plays an important role especially in food and flavour chemistry because it contributes to the aroma of several foodstuffs including wine. Although 3 can be formed by chemical reactions during food preparation, it is also produced by microorganisms. Recent studies with yeasts showed that methionine (1) is a potential precursor of 3, but the mechanism of the transformation is unknown. The biosynthetic pathway leading to 3 in the bacterium Chitinophaga Fx7914 was probed. Extensive feeding experiments with differently labelled precursors by using liquid cultures of Chitinophaga Fx7914 were performed. The volatiles released by the bacterium were collected by using a closed loop stripping apparatus (CLSA) and analysed by GC-MS. The observed incorporation pattern of the precursors into 3 led to the elucidation of the biosynthetic pathway. One part of the compound 2 originates from homocysteine (15), which is transformed into 3-mercaptopropanal (17). The second biosynthetic building block is pyruvate (14). An acyloin-forming reaction furnishes the key intermediate 21, which cyclises intramolecularly to a diol. Dehydration followed by tautomerisation lead to the cyclic ketone 3, which is produced by the bacterium in racemic form.
Thorben Nawrath; Klaus Gerth; Rolf Müller; Stefan Schulz
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Publication Detail:
Type:  Journal Article; Research Support, Non-U.S. Gov't    
Journal Detail:
Title:  Chembiochem : a European journal of chemical biology     Volume:  11     ISSN:  1439-7633     ISO Abbreviation:  Chembiochem     Publication Date:  2010 Sep 
Date Detail:
Created Date:  2010-09-06     Completed Date:  2011-01-04     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  100937360     Medline TA:  Chembiochem     Country:  Germany    
Other Details:
Languages:  eng     Pagination:  1914-9     Citation Subset:  IM    
Institut für Organische Chemie, Technische Universität Braunschweig, Hagenring 30, 38106 Braunschweig, Germany.
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MeSH Terms
Homocysteine / chemistry
Isotope Labeling
Mass Spectrometry
Methionine / chemistry
Pyruvic Acid / chemistry
Sphingobacterium / chemistry,  metabolism*
Thiophenes / chemistry,  metabolism*
Reg. No./Substance:
0/2-methyltetrahydrothiophen-3-one; 0/Thiophenes; 127-17-3/Pyruvic Acid; 454-28-4/Homocysteine; 63-68-3/Methionine

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

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