Microbial transformation of aliphatic aldehydes by Bacillus megaterium to 2,3-dialkylacroleins.
The biotransformation of a series of aliphatic aldehydes (C(8)-C(12)) by Bacillus megaterium isolated from strawberry leaf surfaces was investigated. Products were isolated by liquid/liquid extraction and analyzed by gas chromatography (GC) combined with mass spectrometry (MS). In addition to aliphatic alcohols and the remaining aldehydes, major transformation products included the corresponding acids as well as 2,3-dialkylacroleins, dehydrated aldol addition products, which were detected for the first time as biotransformation products. To verify the structures, 2,3-dialkylacroleins were chemically synthesized from the appropriate aldehydes by base-catalyzed aldol condensation reactions and characterized by (1)H and (13)C NMR spectroscopy. Time-course studies showed that the maximum yield of the acrolein derivatives was obtained after 6 days of incubation.
Abanda-Nkpwatt
Daniel
D
Biomolecular Food Technology, Technical University Munich, Lise-Meitner-Strasse 34, D-85354 Freising, Germany.
Schwab
Wilfried
W
D000171:Acrolein / Q000031:analogs & derivatives* / Q000378:metabolism*; D000447:Aldehydes / Q000378:metabolism*; D001410:Bacillus megaterium / Q000378:metabolism*; D001711:Biotransformation; D031985:Fragaria / Q000382:microbiology; D007700:Kinetics; D009682:Magnetic Resonance Spectroscopy; D018515:Plant Leaves / Q000382:microbiology
D000447:Aldehydes; D000171:Acrolein