Biocatalytic production of 10-hydroxystearic acid, 10-ketostearic acid, and their primary fatty amides

The objective of this study was to develop scaleup bioprocesses for producing 10-hydroxystearic acid (10-HSA) and 10-ketostearic acid (10-KSA) as well as their primary amides for potential new uses. A reactor process was examined to obtain the mono-oxygenated FA using Sphingobacterium thalpophilum (NRRL B-1 4797) and Bacillus sphaericus (NRRL NRS-732), which solely produce 10-HSA and 10-KSA, respectively, from technical-grade oleic acid. By using an 8-h-old B-1 4797 culture grown in a manganese-containing WF6 medium, pH 7.3, at 28 degrees C under 350 rpm agitation and 0-50% dissolved oxygen concentrations provided by a controlled sparger aeration, the production of 10-HSA reached 7 g/L with a 40% yield in 4 d. In using a 12-h-old NRS-732 culture grown in a pyruvate-containing PF6 medium, pH 6.5, at 30 degrees C under 750 rpm agitation without any sparger aeration during the conversion reaction, 10-KSA production reached 7.9 g/L with a yield of more than 54% in 72 h. The scaleup reactor process provided crystalline 10-HSA and 10-KSA for producing new primary amides via a lipase-catalyzed amidation reaction with yields of 94 and 92%, respectively. The primary amides of 10-HSA and 10-KSA displayed m.p. of 115 and 120 degrees C, respectively.