10-hydroxystearic acid isolate

It has been reported that a microbial isolate, Flavobacterium sp. strain DS5, produced 10-ketostearic acid (10-KSA) from oleic acid in 85% yield (Hou, 1994a). The purified product was white, plate-like crystals melting at 79.2°C. A small amount of 10-hydroxystearic acid (10-HSA) was also produced during the bioconversion, suggesting that oleic acid is converted to 10-KSA via 10-HSA, and the enzyme catalyzing the hydration is C-10 positional specific (Hou, 1994b, 1995). The DS5 bioconversion products from oleic, linoleic, a-linolenic, and y-linolenic acid are all 10-hydroxy fatty acids. The optimum time, pH, and temperature for the production of 10-KSA have been reported in flask... 

By using the squalene screening method (11), Seo et al. (12) isolated a culture, Corynebacterium sp. S-401, from soil, that hydrates the squalene molecule to form tertiary alcohols. They found that resting eells of strain S-401 also stereospecifically hydrated oleic acid to 10-ketostearic (10-KSA) and (-)-10i -hydroxystearic acids with 22.4 and 9.1% yield, respectively. Strain S-401 failed to catalyze hydration of... 

Kaneshiro, T., J.-K. Huang, D. Weisleder, and M.O. Bagby, 10i -Hydroxystearic Acid Production by a Novel Microbe, NRRL B-14797, Isolated from Compost, J. Ind. Microbiol. 13 351-355 (1994). 

Wallen et al. described the hydration of oleic acid to hydroxystearic acid by a Pseudomonas strain 3266 already in the 1960s (Davis et al. 1969). Several bacterial strains have been isolated that are able to hydrate oleic acid and in some case catalyze the subsequent oxidation to 10-ketostearic acid (Heo and Kim 2009 Kuo et al. 2000, 2002 Kuo and Levinson 2006). The reaction shows moderate stereospecificity (Gocho et al. 1995). Two groups cloned independently the hydratases from the Pseudomonas strain 3266 (Bevers et al. 2009) and Streptococcus pyogenes... 

Kuo TM, Levinson WE (2006) Biocatalytic production of 10-hydroxystearic acid, 10-ketosteaiic acid, and their primary fatty amides. Agriculture 83(8) 671-675 Kuo TM, Lanser AC, Nakamura LK, Hou CT (2000) Production of 10-ketostearic acid and 10-hydroxystearic acid by strains of Sphingobacterium thalpophilum isolated fi om composted manure. Curr Microbiol 40 105-109. doi 10.1007/s002849910020... 

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