Microbial hydration ofCis‐9‐alkenoic acids
- 1 September 1969
- Vol. 4 (5) , 356-362
- https://doi.org/10.1007/bf02531006
Abstract
The activity of acis‐9‐fatty acid hydratase produced by aPseudomonas sp. (NRRL B‐3266) isolated from soil was compared with that of another isolate previously reported (NRRL B‐2994). The presence of appropriate fatty acids for at least 4 hr during aerobic growth in yeast extract medium increased subsequent enzyme activity. Such cells anaerobically hydrated severalcis‐9‐alkenoic acids to 10‐hydroxy fatty acids and aerobically formed 10‐keto acids, which were partially degraded to shorter chain keto acids. Melting point, gas chromatography, infrared, mass spectrometry and optical rotatory dispersion data are given. Six fatty acids havingcis‐9‐unsaturation produced hydrated products, but several enoic acids havingtrans‐9‐unsaturation or double bonds in other than the 9 position were inactive as substrates. The (−)‐10‐hydroxypalmitic acid produced from palmitoleic acid is considered to have the D configuration. Yields of 71% crude crystalline product from 15 g of oleic acid and 53% from 11 g of palmitoleic acid were obtained in 5‐liter anaerobic fermentations with NRRL B‐3266. Methyl esters, triolein and oleyl alcohol were not hydrated.Keywords
This publication has 8 references indexed in Scilit:
- Seed LipidsScience, 1966
- The Stereospecific Conversion of Stearic Acid to Oleic AcidJournal of Biological Chemistry, 1965
- Search for new industrial oils. viii. the genuslimnanthesJournal of Oil & Fat Industries, 1964
- Enzymatic Stereospecifity in the Dehydrogenation of Stearic Acid to Oleic AcidJournal of the American Chemical Society, 1963
- The microbiological production of 10-Hydroxystearic acid from oleic acidArchives of Biochemistry and Biophysics, 1962
- Maintenance of Cultures of Industrially Important Microorganisms1Applied Microbiology, 1955