A recombinant enzyme from Lysinibacillus fusiformis was expressed, purified, and identified as an oleate hydratase because the hydration activity of the enzyme was the highest for oleic acid (with a k cat of 850 min−1 and a K m of 540 μM), followed by palmitoleic acid, γ-linolenic acid, linoleic acid, myristoleic acid, and α-linolenic acid. The optimal reaction conditions for the enzymatic production of 10-hydroxystearic acid were pH 6.5, 35 °C, 4% (v/v) ethanol, 2,500 U ml−1 (8.3 mg ml−1) of enzyme, and 40 g l−1 oleic acid. Under these conditions, 40 g l−1 (142 mM) oleic acid was converted into 40 g l−1 (133 mM) 10-hydroxystearic acid for 150 min, with a molar yield of 94% and a productivity of 16 g l−1 h−1, and olive oil hydrolyzate containing 40 g l−1 oleic acid was converted into 40 g l−1 10-hydroxystearic acid for 300 min, with a productivity of 8 g l−1 h−1.
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Bagby MO, Calson KD (1989) Chemical and biological conversion of soybean oil for industrial products. In: Cambie RC (ed) Fats for the future. Ellis Horwood, Chichester, pp 301–317
Bevers LE, Pinkse MW, Verhaert PD, Hagen WR (2009) Oleate hydratase catalyzes the hydration of a nonactivated carbon-carbon bond. J Bacteriol 191:5010–5012
Chen TC, Ju YH (2001) An improved fractional crystallization method for the enrichment of gamma-linolenic acid in borage oil fatty acid. Ind Eng Chem Res 40:3781–3784
el-Sharkawy SH, Yang W, Dostal L, Rosazza JP (1992) Microbial oxidation of oleic acid. Appl Environ Microbiol 58:2116–2122
Garcia EE, Belin JM, Wache Y (2007) Use of a Doehlert factorial design to investigate the effects of pH and aeration on the accumulation of lactones by Yarrowia lipolytica. J Appl Microbiol 103:1508–1515
Heo SH, Kim BS (2009) Production and recovery of oxygenated fatty acids from oleic acid by Flavobacterium sp. strain DS5. Korean Chem Eng Res 47:620–623
Hou CT (1994a) Conversion of linoleic acid to 10-hydroxy-12(Z)-octadecenoic acid by Flavobacterium sp. (NRRL B-14859). J Am Oil Chem Soc 71:975–978
Hou CT (1994b) Production of 10-ketostearic acid from oleic acid by Flavobacterium sp. strain DS5 (NRRL B-14859). Appl Environ Microbiol 60:3760–3763
Hou CT (1995a) Is strain DS5 hydratase a C-10 positional specific enzyme? Identification of bioconversion products from α- and γ-linolenic acids by Flavibacterium sp. DS5. J Ind Microbiol 14:31–34
Hou CT (1995b) Production of hydroxy fatty acids from unsaturated fatty acids by Flavobacterium sp. DS5 hydratase, a C-10 positional- and cis unsaturation-specific enzyme. J Am Oil Chem Soc 72:1265–1270
Hudson JA, MacKenzie CA, Joblin KN (1995) Conversion of oleic acid to 10-hydroxystearic acid by two species of ruminal bacteria. Appl Microbiol Biotechnol 44:1–6
Kim BN, Yeom SJ, Oh DK (2011) Conversion of oleic acid to 10-hydroxystearic acid by whole cells of Stenotrophomonas nitritireducens. Biotechnol Lett 33:993–997
Koritala S, Hosie L, Hou CT, Hesseltine CW, Bagby MO (1989) Microbial conversion of oleic acid to 10-hydroxystearic acid. Appl Microbiol Biotechnol 32:299–304
Kuo TM, Lanser AC, Nakamura LK, Hou CT (2000) Production of 10-ketostearic acid and 10-hydroxystearic acid by strains of Sphingobacterium thalpophilum isolated from composted manure. Curr Microbiol 40:105–109
Latrasse A, Paitier S, Lachot B, Bonnarme P, Feron G, Durand A, Le Quere JL (1997) Conversion of oleic acid to 10-hydroxystearic acid by Nocardia paraffinae. Biotechnol Lett 19:715–718
Morvan B, Joblin KN (1999) Hydration of oleic acid by Enterococcus gallinarum, Pediococcus acidilactici and Lactobacillus sp. isolated from the rumen. Anaerobe 5:605–611
Naughton FC (1974) Production, chemistry and commercial applications of various chemicals from castor oil. J Am Oil Chem Soc 51:65–71
Niehaus WG Jr, Torkelson A, Kisic A, Bednarczyk DJ, Schroepfer GJ Jr (1970) Stereospecific hydration of the delta-9 double bond of oleic acid. J Biol Chem 245:3790–3797
Rosberg-Cody E, Liavonchanka A, Gobel C, Ross RP, O’Sullivan O, Fitzgerald GF, Feussner I, Stanton C (2011) Myosin-cross-reactive antigen (MCRA) protein from Bifidobacterium breve is a FAD-dependent fatty acid hydratase which has a function in stress protection. BMC Biochem 12:9–20
Turner NJ (2009) Directed evolution drives the next generation of biocatalysts. Nat Chem Biol 5:567–573
Volkov A, Liavonchanka A, Kamneva O, Fiedler T, Goebel C, Kreikemeyer B, Feussner I (2010) Myosin cross-reactive antigen of Streptococcus pyogenes M49 encodes a fatty acid double bond hydratase that plays a role in oleic acid detoxification and bacterial virulence. J Biol Chem 285:10353–10361
Wache Y, Aguedo M, Choquet A, Gatfield IL, Nicaud JM, Belin JM (2001) Role of beta-oxidation enzymes in gamma-decalactone production by the yeast Yarrowia lipolytica. Appl Environ Microbiol 67:5700–5704
Yang W, Dostal L, Rosazza JP (1993) Stereospecificity of microbial hydrations of oleic acid to 10-hydroxystearic acid. Appl Environ Microbiol 59:281–284
This study was supported by a grant (Code#000407980110) from Small and Medium Business Administration, Republic of Korea.
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Kim, BN., Joo, YC., Kim, YS. et al. Production of 10-hydroxystearic acid from oleic acid and olive oil hydrolyzate by an oleate hydratase from Lysinibacillus fusiformis . Appl Microbiol Biotechnol 95, 929–937 (2012). https://doi.org/10.1007/s00253-011-3805-2
- Lysinibacillus fusiformis
- Oleic acid
- 10-Hydroxystearic acid production
- Oleate hydratase
- Olive oil hydrolyzate