Microbial Transformation of Aliphatic Aldehydes byBacillus megateriumto 2,3-Dialkylacroleins

Abstract

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.

Characterizing NAD-Dependent Alcohol Dehydrogenase Enzymes of Methylobacterium extorquens and Strawberry (Fragaria × ananassa cv. Elsanta)

“…It is also noticeable that not only M. extorquens but also other bacteria such as Bacillus megaterium, which can also be found in strawberries, can participate in the formation of chemicals that are useful for plant interactions such as acroleins (25). Our current work focuses on the interactions of bacterial (M. extorquens) and strawberry (Fragaria × ananassa cv.…”

Natural Occurrence of Aldol Condensation Products in Valencia Orange Oil

“…2‐Butyl‐2‐octenal, 2‐hexyl‐2‐decenal, 2‐octyl‐2‐dodecenal and 2‐nonyl‐2‐tridecenal were synthesized from hexanal, octanal, decanal, and undecanal, respectively, each under different pH conditions. The aldol self‐condensation was catalyzed by sodium hydroxide for hexanal (Robert and others ), amine immobilized on silica for octanal (Shimizu and others ), diethylaminotrimethylsilane for decanal (Hagiwara and others ), and sodium hydride for undecanal (Abanda‐Nkpwatt and Schwab ). In this latter synthesis sodium hydride was used as the catalyst.…”