Summary
Resting cell suspensions of seven Nocardia species catalyzed the production of 10-hydroxystearic acid from oleic acid. Nocardia cholesterolicum NRRL 5767 gave a good yield with optimum conditions at pH 6.5 and 40°C. Yields exceeding 90% can be obtained within 6 h with 0.1 g cells (dry weight) and 178 mg oleic acid in 10 ml of 0.05 M sodium phosphate buffer (pH 6.5). In addition, minor amounts of 10-ketostearic acid were formed as a by-product. The reaction proceeded via hydration of the double bond as shown by labeling experiments with deuterium oxide and 18O-labeled water. The system was specific for fatty acids with cis unsaturation at the 9 position.
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Achaya KT (1971) Chemical derivatives of castor oil. J Am Oil Chem Soc 48:758–763
Davis EN, Wallen LL, Goodwin JC, Rohwedder WK, Rhodes RA (1969) Microbial hydroxylation of cis-9-alkenoic acids. Lipids 4:356–362
Findley TW, Swern D, Scanlan JT (1945) Epoxidation of unsaturated fatty materials with peracetic acid in glacial acetic acid solution. J Am Chem Soc 67:412–414
Formo MW (1979) Paints, varnishes and related products. In: Swern D (ed) Bailey's industrial oil and fat products, vol 1, 4th edn. Wiley, New York, pp 687–816
Litchfield JH, Pierce GE (1986) Microbiological synthesis of hydroxy-fatty acids and keto-fatty acids. US patent no. 4582804
Morris LJ, Hall SW, James AT (1966) The biosynthesis of ricinoleic acid by Claviceps purpurea. Biochem J 100:29C-30C
Niehaus WG Jr, Kisic A, Torkelson A, Bednarczyk DJ, Schroepfer GJ Jr (1970) Stereospecific hydration of the Δ9-double bond of oleic acid. J Biol Chem 245:3790–3797
Schroepfer GJ Jr (1965) Enzymatic stereospecificity in the converison of oleic acid to 10-hydroxystearic acid. J Am Chem Soc 87:1411–1412
Schroepfer GJ Jr (1966) Stereospecific conversion of oleic acid to 10-hydroxystearic acid. J Biol Chem 241:5441–5447
Ryhage R, Stenhagen E (1960) Mass spectrometry of long-chain esters. Arkiv Kemi 15:545–560
Wallen LL, Benedict RG, Jackson RW (1962) The microbiological production of 10-hydroxystearic acid from oleic acid. Arch Biochem Biophys 99:249–253
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Koritala, S., Hou, C.T., Hesseltine, C.W. et al. Microbial conversion of oleic acid to 10-hydroxystearic acid. Appl Microbiol Biotechnol 32, 299–304 (1989). https://doi.org/10.1007/BF00184978
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DOI: https://doi.org/10.1007/BF00184978