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Appl Environ Microbiol. 1994 October; 60(10): 3760-3763
Copyright © 1994, American Society for Microbiology. All Rights Reserved.

Production of 10-Ketostearic Acid from Oleic Acid by Flavobacterium sp. Strain DS5 (NRRL B-14859)

Ching T. Hou*

1 Oil Chemical Research, National Center for Agricultural Utilization Research, Agricultural Research Service, U.S. Department of Agriculture, Peoria, Illinois 61604

ABSTRACT

A microbial isolate, Flavobacterium sp. strain DS5, produces 10-ketostearic acid (10-KSA) from oleic acid in 85% yield. This is the first report on this type of reaction catalyzed by a Flavobacterium strain. The product was purified to give white, plate-like crystals melting at 79.2°C. The optimum time, pH, and temperature for the production of 10-KSA are 36 h, 7.5, and 30°C, respectively. A small amount of 10-hydroxystearic acid (10-HSA) (about 10% of the amount of the main product, 10-KSA) is also produced during the bioconversion. 10-KSA is not further metabolized by strain DS5 and accumulates in the medium. In contrast to growing cells, a resting-cell suspension of strain DS5 produces 10-HSA and 10-KSA in a ratio of 1:3. The crude cell extract obtained from ultrasonic disruption of the cells converts oleic acid mainly to 10-HSA (10-HSA/10-KSA ratio, 97:3). This result strongly suggested that oleic acid is converted to 10-KSA via 10-HSA. Enzymes catalyzing the hydration and secondary alcohol dehydrogenation are cell associated. Product 10-HSA from strain DS5 is 66% enantiomeric excess in the 10(R) form. The oleic acid conversion enzyme(s) reacts with unsaturated fatty acids in the order oleic acid > palmitoleic acid > linoleic acid > linolenic acid > {gamma}-linolenic acid > myristoleic acid.

FOOTNOTES

* Mailing address: Oil Chemical Research, NCAUR/ARS/USDA, 1815 N. University St., Peoria, IL 61604. Phone: (309) 681-6263. Fax: (309) 681-6686.

Appl Environ Microbiol. 1994 October; 60(10): 3760-3763
Copyright © 1994, American Society for Microbiology. All Rights Reserved.



This article has been cited by other articles:

  • Jenkins, T. C., AbuGhazaleh, A. A., Freeman, S., Thies, E. J. (2006). The Production of 10-Hydroxystearic and 10-Ketostearic Acids Is an Alternative Route of Oleic Acid Transformation by the Ruminal Microbiota in Cattle. J. Nutr. 136: 926-931 [Abstract] [Full Text]  


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