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

Abstract

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‐14797) 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‐14797 culture grown in a manganese‐containing WF6 medium, pH 7.3, at 28°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°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 producting 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°C, respectively.

Configurational Assignment of ‘Cryptochiral’ 10‐Hydroxystearic Acid Through an Asymmetric Catalytic Synthesis

“…= 1.3, 1 H). Undeca-9,10-dienoic Acid (15). Identified analytically in mixtures obtained according to GP1 (cf.…”

Oxidation of unsaturated fatty acid derivatives and vegetable oils

“…Kuo and Levinson reported on investigations to develop processes for producing 10-hydroxystearic acid and 10ketostearic acid as well as their primary fatty amides [165]. Technical-grade oleic acid was oxidized exclusively in the 10position using Sphingobacterium thalpophilum (NRRL B-14797) and Bacillus sphaericus (NRRL NRS-732), Furthermore, Kuo et al [166] reported that, among 57 Bacillus sphaericus-like strains tested, ten selectively converted oleic acid to 10-ketostearic acid.…”

Bacterial Biotransformation of Oleic Acid: New Findings on the Formation of γ-Dodecalactone and 10-Ketostearic Acid in the Culture of Micrococcus luteus

“…Application of biocatalysts possessing high oxidation activity against unsaturated fatty acids could be an attractive oxofunctionalization alternative to harmful processes based on chemical synthesis. Both hydroxy and keto fatty acids are widely used as starting materials for plasticizers, lubricants and emulsifiers [ 59 , 62 , 63 , 64 ]. Prochiral long chain keto fatty acids can be important precursors in stereoselective microbial reduction, providing optically active hydroxy fatty acids.…”

“…Hydroxy and keto fatty acids are manufactured from fats and oils by chemical reactions or, in a more environmentally friendly way, by using biocatalysis. They are important industrial chemicals used in plasticizer, lubricant, surfactant and detergent formulations [ 59 , 62 , 63 , 64 ].…”