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

Author:
Kuo, Tsung Min, Levinson, William E.
Source:
Journal of the American Oil Chemists' Society 2006 v.83 no.8 pp. 671
ISSN:
0003-021X
Subject:
oleic acid, biotransformation, oxidation, lipid metabolism, amides, stearic acid, Sphingobacterium thalpophilum, Bacillus sphaericus, soil bacteria, bioreactors
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.
Agid:
8173
Handle:
10113/8173