Comparison of Biochemical Properties of the Original. and Newly Identified Oleate Hydratases from
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1 Comparison of Biochemical Properties of the Original and Newly Identified Oleate Hydratases from Stenotrophomonas maltophilia Woo-Ri Kang, a Min-Ju Seo, a Kyung-Chul Shin, a Jin-Byung Park, b Deok-Kun Oh a a Department of Bioscience and Biotechnology, Konkuk University, Seoul 05029, Republic of Korea b Department of Food Science and Engineering, Ewha Womans University, Seoul 03760, Republic of Korea Address correspondence to Deok-Kun Oh, deokkun@konkuk.ac.kr. 1
2 Supplemental material A B C 2
3 D Molecular mass (kda) Retention time (min) FIG S1. Molecular masses of OhyA1 and OhyA2 from S. maltophilia. SDS-PAGE analysis of (A) OhyA1 and (B) OhyA2 from S. maltophilia. Lane M, marker proteins; lane 1, pellet; lane 2, crude extract; lane 3, purified enzyme from His-Trap HP column chromatography. Molecular mass determination of (C) OhyA1 and (D) OhyA2 by gel filtration chromatography. The column was calibrated by measuring the retention time of thyroglobulin (669 kda), ferritin (440 kda), aldolase (158 kda), and ovalbumin (43 kda) as reference proteins. OhyA1 and OhyA2 was eluted at a retention time corresponding to 136 kda and 152 kda, respectively. 3
4 A Relative activity (%) Temperature ( o C) B Relative activity (%) ph FIG S2. Effects of temperature and ph on the hydration activities of OhyA1 and OhyA2 from S. maltophilia. (A) Effect of temperature. The reactions were performed in 50 mm 4
5 citrate/phosphate buffer (ph 6.0) containing 0.01 mg/ml OhyA1 ( ) and mg/ml OhyA2 ( ), 0.5 mm oleic acid in the presence of 5% (v/v) DMSO for 10 min by varying the temperature from 25 to 50 C. At the relative 100%, 0.09 mm 10-hydroxystearic acid was produced. (B) Effect of ph. The reactions were performed in 50 mm citrate/phosphate (ph ) buffer containing 0.01 mg/ml OhyA1 ( ) and mg/ml OhyA2 ( ), 0.5 mm oleic acid in the presence of 5% (v/v) DMSO at 35 C for 10 min. Data represent the mean ± standard deviation of three independent experiments. 5
6 A B Relative activity (%) Control Methanol Ethanol Isopropanol DMSO Butanol Acetone Toluene Relative activity (%) DMSO concentration (%) 6
7 C D Relative activity (%) Control Methanol Ethanol Isopropanol DMSO Butanol Acetone Toluene Relative activity (%) DMSO concentration (%) FIG S3. Effect of solvent on the hydration activities of OhyA1 and OhyA2 from S. 7
8 maltophilia. (A) Effect of solvent type on the hydration activity of OhyA1. The reactions were performed in 50 mm citrate/phosphate buffer (ph 6.0) containing 0.01 mg ml 1 OhyA1, 0.5 mm oleic acid, and 5% (v/v) ( ), or 10% (v/v) ( ) solvent at 35 C for 10 min. Control indicates the reactions without the addition of solvents. (B) Effect of DMSO concentration on the hydration activity of OhyA1. The reactions were performed in 50 mm citrate/phosphate buffer (ph 6.0) containing 0.01 mg/ml OhyA1 and 0.5 mm oleic acid at 35 C for 10 min by varying the DMSO concentration from 0 to 10%. (C) Effect of solvent type on the hydration activity of OhyA2. The reactions were performed in 50 mm citrate/phosphate buffer (ph 6.0) containing mg/ml OhyA2, 0.5 mm oleic acid, and 5% (v/v) ( ), or 10% (v/v) ( ) solvent at 35 C for 10 min. Control indicates reactions without the addition of solvents. (D) Effect of DMSO concentration on the hydration activity of OhyA2. The reactions were performed in 50 mm citrate/phosphate buffer (ph 6.0) containing mg/ml OhyA2 and 0.5 mm oleic acid at 35 C for 10 min by varying the DMSO concentration from 0 to 10%. Data represent the mean ± standard deviation of three independent experiments. 8
9 FIG S4. Absorbance of apo- and holo-ohyas from S. maltophilia and FAD. Spectra were recorded with 1 mg/ml enzymes. The spectra of apo-ohya1, and apo-ohya2 are shown in purple and blue, respectively, and show linear forms above about 320 nm. The spectra of holo-ohya1, holo-ohya2, and FAD are shown in green, orange, and red, respectively. 9
10 Relative activity (%) Untreated FAD FADH 2 FAD+NADH FAD+DTT FIG S5. Effect of the addition of cofactors on the hydration activities of OhyA1 and OhyA2 from S. maltophilia for oleic acid. The reactions were performed with cofactor in 50 mm citrate/phosphate buffer (ph 6.0) containing 0.01 mg/ml OhyA1 ( ) or mg/ml OhyA2 ( ), 0.5 mm oleic acid, and 5% (vol/vol) DMSO at 35 C for 10 min. The cofactors used were 0.1 mm FAD, 0.1 mm FADH 2, 0.1 mm FAD supplemented with 5 mm NADH, and 0.1 mm FAD supplemented with 5 mm DTT. Untreated indicates that the reaction was performed without the addition of cofactors. The relative activity of untreated was 100%. Data represent the mean ± standard deviation of three independent experiments. 10
11 FIG S6. Multiple sequence alignment of OhyA1s from L. fusiformis (Lf_OhyA1), M. caseolyticus (Mc_OhyA1), S. pyogenes (Sp_OhyA1), S. maltophilia (Sm_OhyA1), and B. breve (Bb_OhyA1); OhyA2s from S. nitritireducens (Sn_OhyA1), S. maltophilia (Sm_OhyaA2), and E. meningoseptica (Em_OhyA2). Based on the crystal structure of OhyA from E. meningoseptica, the conserved amino acids of the active site, such as close to the double bond (E122, Y241, and Y456) and the carboxylate group (Q265, T436, N438, and H442) of oleic acid, are presented as white letters on gray backgrounds. 11
12 A B 12
13 C D FIG S7. Proposed structures of the FAD-binding motifs of OhyAs from S. maltophilia complexed with FAD as the cofactor. (A) Wild-type OhyA1. (B) E50A variant OhyA1 13
14 docked with FAD. (C) Wild-type OhyA2. (D) A86E variant OhyA2. FAD, FAD-binding motif, and active-site residues are shown in yellow, blue, and red, respectively. 14
15 TABLE S1 Relative activities of holo-ohyas, apo-ohyas, and apo-ohyas with FAD from S. maltophilia a Enzyme Relative activity (%) Holo-OhyA1 100 Apo-OhyA1 0.1 Apo-OhyA1 + FAD 8.7 Holo-OhyA2 100 Apo-OhyA2 7.0 Apo-OhyA2 + FAD 31.7 a The reactions were performed in 50 mm citrate/phosphate buffer (ph 6.0) containing 0.01 mg/ml OhyA1 or mg/ml OhyA2, 0.5 mm unsaturated fatty acid, and 5% (vol/vol) DMSO at 35 C for 10 min. 15
16 TABLE S2 Molecular mass, optimum ph and temperature, and cofactor dependence of holoenzyme for bacterial OhyAs Type Microorganisms GenBank accession No. Subunit Quaternary Optimum Optimum Cofactor Reference mol wt (kda) structure ph temp ( C) dependence of holoenzyme OhyA1 L. fusiformis ZP_ Dimer (+) FAD b 1 M. caseolyticus NC_ Dimer (+) FAD b 2 S. pyogenes ZP_ a NR NR NR NR 3 S. maltophilia WP_ Dimer (+) FAD, NADP + This study B. breve WP_ NR NR NR NR 4 OhyA2 E. meningoseptica GQ_ NR NR 5 S. nitritireducens KX_ Dimer ( ) b 6 S. maltophilia WP_ Dimer ( ) This study a Calculated value based on the reported sequence in GenBank b This study NR, not reported 16
17 TABLE S3 Amino acid sequence identity of bacterial OhyAs Type OhyA1 (%) OhyA2 (%) Source L. fusiformis M. caseolyticus S. pyogenes S. maltophilia B. breve S. nitritireducens S. maltophilia E. meningoseptica OhyA1 L. fusiformis M. caseolyticus S. pyogenes S. maltophilia B. breve OhyA2 S. nitritireducens S. maltophilia E. meningoseptica
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