Biochemical characterization and FAD-binding analysis of oleate hydratase from Macrococcus caseolyticus

Biochimie

Volumn 94, Issue 3, 2012, Pages 907-915

  Joo, Young Chul ^a   Jeong, Ki Woong ^a   Yeom, Soo Jin ^a   Kim, Yeong Su ^a   Kim, Yangmee ^a   Oh, Deok Kun ^a  

^a Konkuk University   (South Korea)

Author keywords

Characterization; FAD binding; Hydroxy fatty acid; Oleate hydratase; Substrate specificity

Indexed keywords

FATTY ACID; FLAVINE ADENINE NUCLEOTIDE; HYDROLYASE; OLEATE HYDRATASE; OLEIC ACID; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; ENZYME ACTIVITY; ENZYME BINDING; ENZYME SPECIFICITY; GRAM POSITIVE COCCI; HYDRATION; MACROCOCCUS CASEOLYTICUS; MOLECULAR CLONING; MOLECULAR WEIGHT; NONHUMAN; NUCLEOTIDE SEQUENCE; PH;

FLAVIN-ADENINE DINUCLEOTIDE; HYDRO-LYASES; OLEIC ACID; PROTEIN BINDING; STAPHYLOCOCCACEAE;

ESCHERICHIA COLI; MACROCOCCUS CASEOLYTICUS;

EID: 84857039505     PISSN: 03009084     EISSN: 61831638     Source Type: Journal    
DOI: 10.1016/j.biochi.2011.12.011     Document Type: Article

References (31)

1. D.G. Hayes The catalytic activity of lipases toward hydroxy fatty acids - a review J. Am. Oil Chem. Soc. 73 1996 543 549 (Pubitemid 126606643)
2. A.D. Ibrahim, H. Hussaini, A. Sani, A.A. Aliero, and S.E. Yakubu Volatile metabolites profiling to discriminate diseases of tomato fruits inoculated with three toxigenic fungal pathogens Res. Biotechnol. 2 2011 14 22
3. Y. Suzuki, O. Kurita, Y. Kono, H. Hyakutake, and A. Sakurai Structure of a new antifungal C11-hydroxyfatty acid isolated from leaves of wild rice Biosci. Biotechnol. Biochem. 59 1995 2049 2051 (Pubitemid 3019219)
4. B.L. Hilker, H. Fukushige, C. Hou, and D. Hildebrand Comparison of Bacillus monooxygenase genes for unique fatty acid production Prog. Lipid Res. 47 2008 1 14 (Pubitemid 350216619)
5. W.H. Eschenfeldt, Y. Zhang, H. Samaha, L. Stols, L.D. Eirich, C.R. Wilson, and M.I. Donnelly Transformation of fatty acids catalyzed by cytochrome P450 monooxygenase enzymes of Candida tropicalis Appl. Environ. Microbiol. 69 2003 5992 5999 (Pubitemid 37280322)
6. F.J. van de Loo, P. Broun, S. Turner, and C. Somerville An oleate 12-hydroxylase from Ricinus communis L. is a fatty acyl desaturase homolog Proc. Natl. Acad. Sci. U.S.A. 92 1995 6743 6747
7. M. Busquets, V. Deroncele, J. Vidal-Mas, E. Rodriguez, A. Guerrero, and A. Manresa Isolation and characterization of a lipoxygenase from Pseudomonas 42A2 responsible for the biotransformation of oleic acid into (S)-(E)-10-hydroxy-8-octadecenoic acid Anton. Leeuw. Int. J. G. 85 2004 129 139 (Pubitemid 38461045)
8. A. Volkov, A. Liavonchanka, O. Kamneva, T. Fiedler, C. Goebel, B. Kreikemeyer, and I. Feussner 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 2010 10353 10361
9. E. Rosberg-Cody, A. Liavonchanka, C. Gobel, R.P. Ross, O. O'Sullivan, G.F. Fitzgerald, I. Feussner, and C. Stanton 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 2011 9 20
10. L.E. Bevers, M.W. Pinkse, P.D. Verhaert, and W.R. Hagen Oleate hydratase catalyzes the hydration of a nonactivated carbon-carbon bond J. Bacteriol. 191 2009 5010 5012
11. T.C. Chen, and Y.H. Ju An improved factional crystallization method for the enrichment of γ-linolenic acid in borage oil fatty acid Ind. Eng. Chem. Res. 40 2001 3781 3784
12. A. Hamahata, Y. Takata, T. Gomi, and M. Fujioka Probing the S-adenosylmethionine-binding site of rat guanidinoacetate methyltransferase. Effect of site-directed mutagenesis of residues that are conserved across mammalian non-nucleic acid methyltransferases Biochem. J. 317 1 1996 141 145
13. J.A. Hudson, C.A. MacKenzie, and K.N. Joblin Conversion of oleic acid to 10-hydroxystearic acid by two species of ruminal bacteria Appl. Microbiol. Biotechnol. 44 1995 1 6
14. K.S. Kil, M.W. Cunningham, and L.A. Barnett Cloning and sequence analysis of a gene encoding a 67-kilodalton myosin-cross-reactive antigen of Streptococcus pyogenes reveals its similarity with class II major histocompatibility antigens Infect. Immun. 62 1994 2440 2449 (Pubitemid 24157075)
15. A. Liavonchanka, E. Hornung, I. Feussner, and M.G. Rudolph Structure and mechanism of the Propionibacterium acnes polyunsaturated fatty acid isomerase Proc. Natl. Acad. Sci. U.S.A. 103 2006 2576 2581
16. E.F. O'Shea, P.D. Cotter, C. Stanton, R.P. Ross, and C. Hill Production of bioactive substances by intestinal bacteria as a basis for explaining probiotic mechanisms: Bacteriocins and conjugated linoleic acid Int. J. Food Microbiol. 2011 10.1016/j.ijfoodmicro.2011.1005.1025
17. S.J. O'Flaherty, and T.R. Klaenhammer Functional and phenotypic characterization of a protein from Lactobacillus acidophilus involved in cell morphology, stress tolerance and adherence to intestinal cells Microbiology 156 2010 3360 3367
18. H. Galbraith, T.B. Miller, A.M. Paton, and J.K. Thompson Antibacterial activity of long chain fatty acids and the reversal with calcium, magnesium, ergocalciferol and cholesterol J. Appl. Bacteriol. 34 1971 803 813
19. C. Henderson The effects of fatty acids on pure cultures of rumen bacteria J. Agric. Sci. 81 1973 107 112
20. H. Keweloh, and H.J. Heipieper Trans unsaturated fatty acids in bacteria Lipids 31 1996 129 137 (Pubitemid 26066080)
21. C.J. Zheng, J.S. Yoo, T.G. Lee, H.Y. Cho, Y.H. Kim, and W.G. Kim Fatty acid synthesis is a target for antibacterial activity of unsaturated fatty acids FEBS Lett. 579 2005 5157 5162 (Pubitemid 41318085)
22. M. Dietrich, S. Eiben, C. Asta, T.A. Do, J. Pleiss, and V.B. Urlacher Cloning, expression and characterisation of CYP102A7, a self-sufficient P450 monooxygenase from Bacillus licheniformis Appl. Microbiol. Biotechnol. 79 2008 931 940
23. C.T. Hou 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 1995 31 34
24. C.T. Hou 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 1995 1265 1270
25. I.S. Yu, S.J. Yeom, H.J. Kim, J.K. Lee, Y.H. Kim, and D.K. Oh Substrate specificity of Stenotrophomonas nitritireducens in the hydroxylation of unsaturated fatty acid Appl. Microbiol. Biotechnol. 78 2008 157 163
26. W.G. Niehaus Jr., and G.J. Schroepfer Jr. The reversible hydration of oleic acid to 10D-hydroxystearic acid Biochem. Biophys. Res. Commun. 21 1965 271 275
27. S. Koritala, C.T. Hou, C.W. Hesseltine, and M.O. Bagby Microbial conversion of oleic acid to 10-hydroxystearic acid Appl. Microbiol. Biotechnol. 32 1989 299 304 (Pubitemid 20053649)
28. G.J. Schroepfer Jr. Stereospecific conversion of oleic acid to 10-hydroxystearic acid J. Biol. Chem. 241 1966 5441 5447
29. Y. Nishiya, and T. Imanaka Analysis of interaction between the Arthrobacter sarcosine oxidase and the coenzyme flavin adenine dinucleotide by site-directed mutagenesis Appl. Environ. Microbiol. 62 1996 2405 2410 (Pubitemid 26231207)
30. O. Dym, and D. Eisenberg Sequence-structure analysis of FAD-containing proteins Protein Sci. 10 2001 1712 1728 (Pubitemid 32848768)
31. R.K. Wierenga, J. Drenth, and G.E. Schulz Comparison of the three-dimensional protein and nucleotide structure of the FAD-binding domain of p-hydroxybenzoate hydroxylase with the FAD- as well as NADPH-binding domains of glutathione reductase J. Mol. Biol. 167 1983 725 739