- Identification and biosynthesis of tropone derivatives and sulfur volatiles produced by bacteria of the marine Roseobacter clade
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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 5-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). The Royal Society of Chemistry 2010.
- Thiel, Verena,Brinkhoff, Thorsten,Dickschat, Jeroen S.,Wickel, Susanne,Grunenberg, Joerg,Wagner-Doebler, Irene,Simon, Meinhard,Schulz, Stefan
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experimental part
p. 234 - 246
(2010/04/29)
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- Synthesis of chalcogenol esters from chalcogenoacetylenes
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Thiol and selenol esters were conveniently prepared in good yields by reacting chalcogenoacetylenes with trifluoroacetic acid in dichloromethane in the presence of silica.
- Braga, Antonio L,Martins, Tales L.C,Silveira, Claudio C,Rodrigues, Oscar E.D
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p. 3297 - 3300
(2007/10/03)
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- TRIFLUOROACETIC ACID IN THE SYNTHESIS OF THIOLCARBAMATES AND S-METHYL ALKANETHIOATES
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The major products of the reaction of 2-bromohexanoic acid with methyl thiocyanate in trifluoroacetic acid are S-methyl 2-bromohexanethioate (II) (55percent yield), S-methyl 2,2,2-trifluoroethanethioate (IV) (31percent yield), N-trifluoroacetyltrifluoroacetamide (V) (11percent yield), and N-trifluoroacetyl-S-methylthiolcarbamate (III) (29percent yield).N-2-Bromohexanoyl-S-methylthiolcarbamate (I), N-2-bromohexanoyltrifluoroacetamide (VI), 2-thiapropioamide (VII), and S-methyl hexanethioate (VIII) are also formed in minor amounts.
- Polivin, Yu. N.,Ageev, E. A.
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p. 178 - 180
(2007/10/02)
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