Microbial conversion of oleic acid to 10-hydroxystearic acid

Abstract

Resting cell suspensions of seven Nocardia species catalyzed the production of 10-hydroxystearic acid from oleic acid. Nocardia cholesterolicum N R R L 5767 gave a good yield with optimum conditions at pH 6.5 and 40 ° C. Yields exceeding 90% can be obtained within 6 h with 0.1 g cells (dry weight) and 178 mg oleic acid in 10 ml of 0.05 M sodium phosphate buffer (pH 6.5). In addition, minor amounts of 10-ketostearic acid were formed as a by-product. The reaction proceeded via hydration of the double bond as shown by labeling experiments with deuterium oxide and 180-labeled water. The system was specific for fatty acids with cis unsaturation at the 9 positon.

Hydration of linoleic acid by bacteria isolated from ruminants

“…Pseudomonas strain NRRL-B-3266 [3], Acetobacterium woodii [4], Nocardia cholesterolicum [5], a Flavobacterium sp. [6], Lactobacillus plantarum [8] and an extract from Pseudomonas strain NRRL-B-2994 [7] have been shown to convert linoleic acid to 10-hydroxy-12-octadecenoic acid.…”

Oleate Hydratase Catalyzes the Hydration of a Nonactivated Carbon-Carbon Bond

“…1) (12). In the following years, many other strains were identified that were also able to convert OA into 10-HSA or to further oxidize it to 10-ketostearic acid (2,3,5,7). The Pseudomonas cells generally start to produce optically pure D-10-HSA in the stationary growth phase, and they do not seem to metabolize it any further, since levels of product accumulate in the fermentation broth.…”

Chirality of the ?-lactones produced bySporidiobolus salmonicolor grown in two different media

“…Pseudomonas sp. 23 and Corynebacteria 24 showed this enzymatic activity towards unsaturated (Z9) fatty acids.…”