1.14.13.236 1,1-diethylcyclopropane + NADH + H+ + O2 - Pseudomonas mendocina ? + NAD+ + H2O - ? 438607 1.14.13.236 1,1-diethylcyclopropane + NADH + H+ + O2 - Pseudomonas mendocina KR1 ? + NAD+ + H2O - ? 438607 1.14.13.236 1,1-dimethylcyclopropane + NADH + H+ + O2 - Pseudomonas mendocina ? + NAD+ + H2O - ? 438608 1.14.13.236 1,1-dimethylcyclopropane + NADH + H+ + O2 - Pseudomonas mendocina KR1 ? + NAD+ + H2O - ? 438608 1.14.13.236 2 fluorobenzene + NADH + H+ + O2 - Pseudomonas mendocina 4-fluorophenol + 4-fluorocatechol + NAD+ + H2O whole-cell reaction, the predominant product is either 4-fluorophenol or 4-fluorocatechol depending on the ratio of biocatalyst to substrate concentration ? 439530 1.14.13.236 2 fluorobenzene + NADH + H+ + O2 - Pseudomonas mendocina KR1 4-fluorophenol + 4-fluorocatechol + NAD+ + H2O whole-cell reaction, the predominant product is either 4-fluorophenol or 4-fluorocatechol depending on the ratio of biocatalyst to substrate concentration ? 439530 1.14.13.236 2 indole + 3 NADH + 3 H+ + 3 O2 - Pseudomonas sp. M4 indirubin + 3 NAD+ + 3 H2O reaction via C-3 oxidation to indoxyl, oxidation to isatin, and recombinantion of isatin and indoxyl to indirubin ? 438663 1.14.13.236 2-phenylethanol + 2 NADH + 2 H+ + O2 - Pseudomonas mendocina 3,4-dihydroxyphenylethanol + 2 NAD+ + 2 H2O reaction of mutants I100A, I100S, I100G ? 438754 1.14.13.236 2-phenylethanol + 2 NADH + 2 H+ + O2 - Pseudomonas mendocina KR1 3,4-dihydroxyphenylethanol + 2 NAD+ + 2 H2O reaction of mutants I100A, I100S, I100G ? 438754 1.14.13.236 2-phenylethanol + NADH + H+ + O2 - Pseudomonas mendocina m-tyrosol + p-tyrosol + NAD+ + H2O 63% m-tyosol + 37% p-tyrosol ? 438755 1.14.13.236 2-phenylethanol + NADH + H+ + O2 - Pseudomonas mendocina KR1 m-tyrosol + p-tyrosol + NAD+ + H2O 63% m-tyosol + 37% p-tyrosol ? 438755 1.14.13.236 2-phenylethanol + NADH + H+ + O2 - Burkholderia cepacia o-tyrosol + m-tyrosol + NAD+ + H2O 64% o-tyrosol + 36% m-tyrosol ? 438756 1.14.13.236 2-phenylethanol + NADH + H+ + O2 - Burkholderia cepacia G4 o-tyrosol + m-tyrosol + NAD+ + H2O 64% o-tyrosol + 36% m-tyrosol ? 438756 1.14.13.236 2-xylene + NADH + H+ + O2 - Pseudomonas mendocina 3,4-dimethylphenol + NAD+ + H2O 95% 3,4-dimethylphenol plus 5% 2-methyl benzyl alcohol ? 438762 1.14.13.236 2-xylene + NADH + H+ + O2 - Pseudomonas mendocina KR1 3,4-dimethylphenol + NAD+ + H2O 95% 3,4-dimethylphenol plus 5% 2-methyl benzyl alcohol ? 438762 1.14.13.236 3-xylene + NADH + H+ + O2 - Pseudomonas mendocina 2,4-dimethylphenol + NAD+ + H2O 97% 2,4-dimethylphenol plus 2.5% 3-methyl benzyl alcohol plus 0.5% 3,5-dimethylphenol ? 438813 1.14.13.236 3-xylene + NADH + H+ + O2 - Pseudomonas mendocina KR1 2,4-dimethylphenol + NAD+ + H2O 97% 2,4-dimethylphenol plus 2.5% 3-methyl benzyl alcohol plus 0.5% 3,5-dimethylphenol ? 438813 1.14.13.236 4-xylene + NADH + H+ + O2 - Pseudomonas mendocina 2,5-dimethylphenol + 4-methyl benzyl alcohol + NAD+ + H2O 82% 2,5-dimethylphenol plus 18% 4-methyl benzyl alcohol ? 438875 1.14.13.236 4-xylene + NADH + H+ + O2 - Pseudomonas mendocina KR1 2,5-dimethylphenol + 4-methyl benzyl alcohol + NAD+ + H2O 82% 2,5-dimethylphenol plus 18% 4-methyl benzyl alcohol ? 438875 1.14.13.236 anisole + NADH + H+ + O2 - Pseudomonas mendocina 4-methoxyphenol + NAD+ + H2O 87% efficiency ? 439131 1.14.13.236 anisole + NADH + H+ + O2 - Pseudomonas mendocina KR1 4-methoxyphenol + NAD+ + H2O 87% efficiency ? 439131 1.14.13.236 benzene + NADH + H+ + O2 - Pseudomonas mendocina phenol + NAD+ + H2O - ? 439243 1.14.13.236 benzene + NADH + H+ + O2 - Pseudomonas mendocina phenol + NAD+ + H2O sole product ? 439243 1.14.13.236 benzene + NADH + H+ + O2 - Pseudomonas mendocina phenol + NAD+ + H2O 98% efficiency ? 439243 1.14.13.236 benzene + NADH + H+ + O2 - Pseudomonas mendocina KR1 phenol + NAD+ + H2O - ? 439243 1.14.13.236 benzene + NADH + H+ + O2 - Pseudomonas mendocina KR1 phenol + NAD+ + H2O 98% efficiency ? 439243 1.14.13.236 benzene + NADH + H+ + O2 - Pseudomonas mendocina KR1 phenol + NAD+ + H2O sole product ? 439243 1.14.13.236 chlorobenzene + NADH + H+ + O2 - Pseudomonas mendocina 4-chlorophenol + NAD+ + H2O 39% efficiency ? 439330 1.14.13.236 chlorobenzene + NADH + H+ + O2 - Pseudomonas mendocina 4-chlorophenol + NAD+ + H2O more than 95% 4-chlorophenol ? 439330 1.14.13.236 chlorobenzene + NADH + H+ + O2 - Pseudomonas mendocina KR1 4-chlorophenol + NAD+ + H2O 39% efficiency ? 439330 1.14.13.236 m-cresol + NADH + H+ + O2 - Pseudomonas mendocina 4-methylcatechol + NAD+ + H2O 100% 4-methylcatechol ? 377122 1.14.13.236 m-cresol + NADH + H+ + O2 - Pseudomonas mendocina KR1 4-methylcatechol + NAD+ + H2O 100% 4-methylcatechol ? 377122 1.14.13.236 m-tyrosol + 2 NADH + 2 H+ + O2 - Burkholderia cepacia 2,3-dihydroxyphenylethanol + 2 NAD+ + 2 H2O 9% 2,3-dihydroxyphenylethanol ? 439719 1.14.13.236 m-tyrosol + 2 NADH + 2 H+ + O2 - Burkholderia cepacia G4 2,3-dihydroxyphenylethanol + 2 NAD+ + 2 H2O 9% 2,3-dihydroxyphenylethanol ? 439719 1.14.13.236 m-tyrosol + 2 NADH + 2 H+ + O2 - Pseudomonas mendocina 3,4-dihydroxyphenylethanol + 2 NAD+ + 2 H2O mutants I100A, I100S, I100D, I100V and I100G hydroxylate m-tyrosol to form 3,4-dihydroxyphenylethanol with conversion of 55%, 50%, 2%, 3% and 18%, respectively ? 439720 1.14.13.236 m-tyrosol + 2 NADH + 2 H+ + O2 - Pseudomonas mendocina KR1 3,4-dihydroxyphenylethanol + 2 NAD+ + 2 H2O mutants I100A, I100S, I100D, I100V and I100G hydroxylate m-tyrosol to form 3,4-dihydroxyphenylethanol with conversion of 55%, 50%, 2%, 3% and 18%, respectively ? 439720 1.14.13.236 methoxybenzene + NADH + H+ + O2 - Pseudomonas mendocina 4-methoxyphenol + NAD+ + H2O more than 99% 4-methoxyphenol ? 439742 1.14.13.236 methyl 4-tolyl sulfide + NADH + H+ + O2 - Pseudomonas mendocina methyl 4-tolyl sulfoxide + NAD+ + H2O (pro-R)-sulfoxide, 41% enantiomeric excess ? 439746 1.14.13.236 methyl 4-tolyl sulfide + NADH + H+ + O2 - Burkholderia cepacia methyl 4-tolyl sulfoxide + NAD+ + H2O (pro-S)-sulfoxide, 11% enantiomeric excess ? 439746 1.14.13.236 methyl 4-tolyl sulfide + NADH + H+ + O2 - Burkholderia cepacia G4 methyl 4-tolyl sulfoxide + NAD+ + H2O (pro-S)-sulfoxide, 11% enantiomeric excess ? 439746 1.14.13.236 methyl 4-tolyl sulfide + NADH + H+ + O2 - Pseudomonas mendocina KR1 methyl 4-tolyl sulfoxide + NAD+ + H2O (pro-R)-sulfoxide, 41% enantiomeric excess ? 439746 1.14.13.236 methyl p-tolyl sulfide + NADH + H+ + O2 - Pseudomonas mendocina methyl p-tolyl sulfoxide + NAD+ + H2O - ? 439747 1.14.13.236 methyl p-tolyl sulfide + NADH + H+ + O2 - Pseudomonas mendocina KR1 methyl p-tolyl sulfoxide + NAD+ + H2O - ? 439747 1.14.13.236 methyl phenyl sulfide + NADH + H+ + O2 - Burkholderia cepacia methyl phenyl sulfoxide + NAD+ + H2O (pro-S)-sulfoxide, 51% enantiomeric excess ? 439748 1.14.13.236 methyl phenyl sulfide + NADH + H+ + O2 - Pseudomonas mendocina methyl phenyl sulfoxide + NAD+ + H2O (pro-S)-sulfoxide, 86% enantiomeric excess ? 439748 1.14.13.236 methyl phenyl sulfide + NADH + H+ + O2 - Burkholderia cepacia G4 methyl phenyl sulfoxide + NAD+ + H2O (pro-S)-sulfoxide, 51% enantiomeric excess ? 439748 1.14.13.236 methyl phenyl sulfide + NADH + H+ + O2 - Pseudomonas mendocina KR1 methyl phenyl sulfoxide + NAD+ + H2O (pro-S)-sulfoxide, 86% enantiomeric excess ? 439748 1.14.13.236 additional information experiments with p-deuterotoluene lead to the isolation of p-cresol which retains 68% of the deuterium initially present in the parent molecule. When incubated with toluene in the presence of 1802, the oxygen in p-cresol is derived from molecular oxygen Pseudomonas mendocina ? - ? 89 1.14.13.236 additional information highly specific for para hydroxylation of toluene, o-xylene, m-xylene Pseudomonas mendocina ? - ? 89 1.14.13.236 additional information no substrates for wild-type: o-tyrosol, m-tyrosol, p-tyrosol Burkholderia cepacia ? - ? 89 1.14.13.236 additional information no substrates for wild-type: o-tyrosol, m-tyrosol, p-tyrosol Pseudomonas mendocina ? - ? 89 1.14.13.236 additional information products are consistent with both radical rearrangement and cation ring expansion. Products show high-fidelity incorporation of an O-atom from O2 in the un-rearranged and radical-rearranged products, while the O-atom found in the cation ring-expansion products is predominantly obtained by reaction with H2O Pseudomonas mendocina ? - ? 89 1.14.13.236 additional information no substrates for wild-type: o-tyrosol, m-tyrosol, p-tyrosol Burkholderia cepacia G4 ? - ? 89 1.14.13.236 additional information highly specific for para hydroxylation of toluene, o-xylene, m-xylene Pseudomonas mendocina KR1 ? - ? 89 1.14.13.236 additional information no substrates for wild-type: o-tyrosol, m-tyrosol, p-tyrosol Pseudomonas mendocina KR1 ? - ? 89 1.14.13.236 additional information products are consistent with both radical rearrangement and cation ring expansion. Products show high-fidelity incorporation of an O-atom from O2 in the un-rearranged and radical-rearranged products, while the O-atom found in the cation ring-expansion products is predominantly obtained by reaction with H2O Pseudomonas mendocina KR1 ? - ? 89 1.14.13.236 additional information experiments with p-deuterotoluene lead to the isolation of p-cresol which retains 68% of the deuterium initially present in the parent molecule. When incubated with toluene in the presence of 1802, the oxygen in p-cresol is derived from molecular oxygen Pseudomonas mendocina KR1 ? - ? 89 1.14.13.236 naphthalene + NADH + H+ + O2 - Pseudomonas mendocina 2-naphthol + NAD+ + H2O - ? 439778 1.14.13.236 naphthalene + NADH + H+ + O2 - Pseudomonas mendocina KR1 2-naphthol + NAD+ + H2O - ? 439778 1.14.13.236 nitrobenzene + NADH + H+ + O2 - Pseudomonas mendocina 4-nitrophenol + NAD+ + H2O 12% efficiency ? 439787 1.14.13.236 nitrobenzene + NADH + H+ + O2 - Pseudomonas mendocina 4-nitrophenol + NAD+ + H2O 88% 4-nitrophenol plus 9% 3-nitrophenol plus 3% 2-nitrophenol ? 439787 1.14.13.236 nitrobenzene + NADH + H+ + O2 - Pseudomonas mendocina KR1 4-nitrophenol + NAD+ + H2O 12% efficiency ? 439787 1.14.13.236 norcarane + NADH + H+ + O2 - Pseudomonas mendocina endo-2-norcaranol + exo-2-norcaranol + endo-3-norcaranol + NAD+ + H2O 72% coupling, 47.5% endo-2-norcaranol, 39.2% exo-2- and endo-3-norcaranol, 8.8% exo-3-norcaranol ? 439792 1.14.13.236 norcarane + NADH + H+ + O2 - Pseudomonas mendocina KR1 endo-2-norcaranol + exo-2-norcaranol + endo-3-norcaranol + NAD+ + H2O 72% coupling, 47.5% endo-2-norcaranol, 39.2% exo-2- and endo-3-norcaranol, 8.8% exo-3-norcaranol ? 439792 1.14.13.236 o-cresol + NADH + H+ + O2 - Pseudomonas mendocina 3-methylcatechol + NAD+ + H2O 91% 3-methylcatechol + 9% methylhydroquinone ? 377392 1.14.13.236 o-cresol + NADH + H+ + O2 - Pseudomonas mendocina KR1 3-methylcatechol + NAD+ + H2O 91% 3-methylcatechol + 9% methylhydroquinone ? 377392 1.14.13.236 o-methoxyphenol + NADH + H+ + O2 - Pseudomonas mendocina 4-methoxyresorcinol + 3-methoxycatechol + NAD+ + H2O 87% 4-methoxyresorcinol, 11% 3-methoxycatechol, and 2% methoxyhydroquinone ? 439793 1.14.13.236 o-methoxyphenol + NADH + H+ + O2 - Pseudomonas mendocina KR1 4-methoxyresorcinol + 3-methoxycatechol + NAD+ + H2O 87% 4-methoxyresorcinol, 11% 3-methoxycatechol, and 2% methoxyhydroquinone ? 439793 1.14.13.236 o-tyrosol + 2 NADH + 2 H+ + O2 - Pseudomonas mendocina 2,3-dihydroxyphenylethanol + 2 NAD+ + 2 H2O mutants I100A, I100S and I100G hydroxylate p-tyrosol to form 3,4-dihydroxyphenylethanol with 24%, 11% and 13% conversion, respectively, respectively ? 439794 1.14.13.236 o-tyrosol + 2 NADH + 2 H+ + O2 - Pseudomonas mendocina KR1 2,3-dihydroxyphenylethanol + 2 NAD+ + 2 H2O mutants I100A, I100S and I100G hydroxylate p-tyrosol to form 3,4-dihydroxyphenylethanol with 24%, 11% and 13% conversion, respectively, respectively ? 439794 1.14.13.236 o-tyrosol + NADH + H+ + O2 - Burkholderia cepacia 2,3-dihydroxyphenylethanol + NAD+ + H2O 83% 2,3-dihydroxyphenylethanol ? 439795 1.14.13.236 o-tyrosol + NADH + H+ + O2 reaction of mutant S395C, 18% conversion in 44 h Pseudomonas mendocina 2,3-dihydroxyphenylethanol + NAD+ + H2O - ? 439795 1.14.13.236 o-tyrosol + NADH + H+ + O2 - Burkholderia cepacia G4 2,3-dihydroxyphenylethanol + NAD+ + H2O 83% 2,3-dihydroxyphenylethanol ? 439795 1.14.13.236 p-cresol + NADH + H+ + O2 - Pseudomonas mendocina 4-methylcatechol + NAD+ + H2O 100% 4-methylcatechol ? 377446 1.14.13.236 p-cresol + NADH + H+ + O2 - Pseudomonas mendocina KR1 4-methylcatechol + NAD+ + H2O 100% 4-methylcatechol ? 377446 1.14.13.236 p-tyrosol + 2 NADH + 2 H+ + O2 - Burkholderia cepacia 3,4-dihydroxyphenylethanol + 2 NAD+ + 2 H2O 10% 3,4-dihydroxyphenylethanol ? 439810 1.14.13.236 p-tyrosol + 2 NADH + 2 H+ + O2 - Pseudomonas mendocina 3,4-dihydroxyphenylethanol + 2 NAD+ + 2 H2O mutants I100A, I100S and I100G hydroxylate p-tyrosol to form 3,4-dihydroxyphenylethanol with 65%, 48% and 98% conversion, respectively, respectively ? 439810 1.14.13.236 p-tyrosol + 2 NADH + 2 H+ + O2 - Burkholderia cepacia G4 3,4-dihydroxyphenylethanol + 2 NAD+ + 2 H2O 10% 3,4-dihydroxyphenylethanol ? 439810 1.14.13.236 phenylethanol + NADH + H+ + O2 - Pseudomonas mendocina m-tyrosol + p-tyrosol + NAD+ + H2O 63% m-tyrosol + 37% p-tyrosol ? 439816 1.14.13.236 phenylethanol + NADH + H+ + O2 - Pseudomonas mendocina KR1 m-tyrosol + p-tyrosol + NAD+ + H2O 63% m-tyrosol + 37% p-tyrosol ? 439816 1.14.13.236 styrene + NADH + H+ + O2 - Pseudomonas mendocina styrene epoxide + NAD+ + H2O - ? 427068 1.14.13.236 styrene + NADH + H+ + O2 - Pseudomonas mendocina KR1 styrene epoxide + NAD+ + H2O - ? 427068 1.14.13.236 toluene + NADH + H+ + O2 - Burkholderia cepacia 4-methylphenol + NAD+ + H2O - ? 439933 1.14.13.236 toluene + NADH + H+ + O2 - Pseudomonas mendocina 4-methylphenol + NAD+ + H2O - ? 439933 1.14.13.236 toluene + NADH + H+ + O2 - Pseudomonas mendocina 4-methylphenol + NAD+ + H2O 194% efficiency ? 439933 1.14.13.236 toluene + NADH + H+ + O2 - Pseudomonas mendocina 4-methylphenol + NAD+ + H2O 94% coupling ? 439933 1.14.13.236 toluene + NADH + H+ + O2 - Pseudomonas mendocina 4-methylphenol + NAD+ + H2O 96% 4-methylphenol + 3% 3-methylphenol ? 439933 1.14.13.236 toluene + NADH + H+ + O2 - Pseudomonas mendocina 4-methylphenol + NAD+ + H2O 96% 4-methylphenol plus 2.8% 3-methylphenol plus 0.4% 2-methylphenol ? 439933 1.14.13.236 toluene + NADH + H+ + O2 - Pseudomonas mendocina 4-methylphenol + NAD+ + H2O 96% 4-methylphenol plus 2.8% 3-methylphenol plus 0.4% 2-methylphenol plus 0.8% benzyl alcohol ? 439933 1.14.13.236 toluene + NADH + H+ + O2 - Pseudomonas mendocina 4-methylphenol + NAD+ + H2O 96.2% 4-methylphenol, 1.5% 3-methylphenol, 0.9% 2-methylphenol, 1.4% benzyl alcohol ? 439933 1.14.13.236 toluene + NADH + H+ + O2 - Burkholderia cepacia G4 4-methylphenol + NAD+ + H2O - ? 439933 1.14.13.236 toluene + NADH + H+ + O2 - Pseudomonas mendocina KR1 4-methylphenol + NAD+ + H2O - ? 439933 1.14.13.236 toluene + NADH + H+ + O2 - Pseudomonas mendocina KR1 4-methylphenol + NAD+ + H2O 96% 4-methylphenol plus 2.8% 3-methylphenol plus 0.4% 2-methylphenol plus 0.8% benzyl alcohol ? 439933 1.14.13.236 toluene + NADH + H+ + O2 - Pseudomonas mendocina KR1 4-methylphenol + NAD+ + H2O 194% efficiency ? 439933 1.14.13.236 toluene + NADH + H+ + O2 - Pseudomonas mendocina KR1 4-methylphenol + NAD+ + H2O 94% coupling ? 439933 1.14.13.236 toluene + NADH + H+ + O2 - Pseudomonas mendocina KR1 4-methylphenol + NAD+ + H2O 96% 4-methylphenol + 3% 3-methylphenol ? 439933 1.14.13.236 toluene + NADH + H+ + O2 - Pseudomonas mendocina p-cresol + NAD+ + H2O - ? 439934 1.14.13.236 toluene + NADH + H+ + O2 - Pseudomonas mendocina KR1 p-cresol + NAD+ + H2O - ? 439934