1.14.13.22 (+)-camphor + NADPH + O2 - Nocardia globerula ? - ? 288491 1.14.13.22 (+)-camphor + NADPH + O2 - Acinetobacter sp. ? - ? 288491 1.14.13.22 (+)-dihydrocarvone + NADPH + O2 - Nocardia globerula ? - ? 288495 1.14.13.22 (+)-dihydrocarvone + NADPH + O2 - Acinetobacter sp. ? - ? 288495 1.14.13.22 (1aS,4aS,8aS)-8a-methylhexahydronaphthalene-1,6-dione + NADPH + O2 Wieland–Miescher ketone, no activity with the (1aR,4aR,8aR)-stereoisomer, stereoselective formation of the cis-(5aR,9aS)-isomer Acinetobacter calcoaceticus (5aR,9aS)-9a-methylhexahydrobenzo[b]oxepine-2,7-dione + NADP+ + H2O - ? 386780 1.14.13.22 (1aS,4aS,8aS)-8a-methylhexahydronaphthalene-1,6-dione + NADPH + O2 Wieland–Miescher ketone, no activity with the (1aR,4aR,8aR)-stereoisomer, stereoselective formation of the cis-(5aR,9aS)-isomer Acinetobacter calcoaceticus NCIMB 9871 (5aR,9aS)-9a-methylhexahydrobenzo[b]oxepine-2,7-dione + NADP+ + H2O - ? 386780 1.14.13.22 (1R)-bicyclo[2.2.1]heptane-2,5-dione + NADPH + O2 74.4% of the activity with cyclohexanone Ilyonectria destructans ? + NADP+ + H2O - ? 425109 1.14.13.22 (2R)-2-ethylcyclohexanone + NADPH + H+ + O2 92% conversion, 30% enantiomeric excess, (-)-product Polaromonas sp. (7S)-7-ethyloxepan-2-one + NADP+ + H2O - ? 425122 1.14.13.22 (2R,6S)-2,6-dimethylcyclohexanone + NADPH + H+ + O2 - Rhodococcus sp. HI-31 cis-3, 7-dimethyl-2-oxepanone + NADP+ + H2O - ? 403021 1.14.13.22 (2R,6S)-2,6-dimethylcyclohexanone + NADPH + O2 + H+ - Acinetobacter calcoaceticus (3R,7S)-3,7-dimethyloxepan-2-one + NADP+ + H2O 90% conversion at 20 h, 99% enantiomeric excess ? 403022 1.14.13.22 (2R,6S)-2,6-dimethylcyclohexanone + NADPH + O2 + H+ - Acinetobacter calcoaceticus NCIMB 9871 (3R,7S)-3,7-dimethyloxepan-2-one + NADP+ + H2O 90% conversion at 20 h, 99% enantiomeric excess ? 403022 1.14.13.22 (2S)-2-(prop-2-en-1-yl)cyclohexanone + NADPH + H+ + O2 75% conversion, 99% enantiomeric excess, (-)-product Polaromonas sp. (7R)-7-(prop-2-en-1-yl)oxepan-2-one + NADP+ + H2O - ? 425124 1.14.13.22 (3R)-3-(1-methylethenyl)cyclohexanone + NADPH + O2 + H+ - Acinetobacter calcoaceticus (6S)-6-(1-methylethenyl)oxepan-2-one + NADP+ + H2O 99% regioselectivity ? 403032 1.14.13.22 (3R)-3-(1-methylethenyl)cyclohexanone + NADPH + O2 + H+ - Acinetobacter calcoaceticus NCIMB 9871 (6S)-6-(1-methylethenyl)oxepan-2-one + NADP+ + H2O 99% regioselectivity ? 403032 1.14.13.22 (4aR,8aS)-8a-methylhexahydronaphthalene-1,6(2H,5H)-dione + NADPH + O2 - Acinetobacter calcoaceticus (5aR,9aS)-9a-methylhexahydrobenzo[b]oxepine-2,7-dione + (4aS,6S,8aR)-6-hydroxy-8a-methyloctahydronaphthalen-1-one + NADP+ + H2O - ? 386864 1.14.13.22 (4aR,8aS)-8a-methylhexahydronaphthalene-1,6(2H,5H)-dione + NADPH + O2 - Acinetobacter calcoaceticus NCIMB 9871 (5aR,9aS)-9a-methylhexahydrobenzo[b]oxepine-2,7-dione + (4aS,6S,8aR)-6-hydroxy-8a-methyloctahydronaphthalen-1-one + NADP+ + H2O - ? 386864 1.14.13.22 (ethylsulfanyl)benzene + NADPH + H+ + O2 - Thermocrispum municipale (R)-ethyl phenyl sulfoxide + NADP+ + H2O - ? 461758 1.14.13.22 (ethylsulfanyl)benzene + NADPH + H+ + O2 - Thermocrispum municipale DSM 44069 (R)-ethyl phenyl sulfoxide + NADP+ + H2O - ? 461758 1.14.13.22 (propylsulfanyl)benzene + NADPH + H+ + O2 - Thermocrispum municipale (R)-propyl phenyl sulfoxide + NADP+ + H2O - ? 461760 1.14.13.22 (propylsulfanyl)benzene + NADPH + H+ + O2 - Thermocrispum municipale DSM 44069 (R)-propyl phenyl sulfoxide + NADP+ + H2O - ? 461760 1.14.13.22 (S)-dithiane sulfoxide + NADPH + O2 recombinant enzyme in E. coli or Saccharomyces cerevisiae Acinetobacter sp. ? - ? 370255 1.14.13.22 1,2-cyclohexandione + NADPH + H+ + O2 18% of the activity with cyclohexanone Arthrobacter sp. ? + NADP+ + H2O - ? 395181 1.14.13.22 1,2-cyclohexandione + NADPH + H+ + O2 2% of the activity with cyclohexanone Rhodococcus sp. ? + NADP+ + H2O - ? 395181 1.14.13.22 1,2-cyclohexandione + NADPH + H+ + O2 24% of the activity with cyclohexanone Rhodococcus sp. ? + NADP+ + H2O - ? 395181 1.14.13.22 1,2-cyclohexandione + NADPH + H+ + O2 7% of the activity with cyclohexanone Arthrobacter sp. ? + NADP+ + H2O - ? 395181 1.14.13.22 1,2-cyclohexandione + NADPH + H+ + O2 24% of the activity with cyclohexanone Rhodococcus sp. TK6 ? + NADP+ + H2O - ? 395181 1.14.13.22 1,2-cyclohexandione + NADPH + H+ + O2 2% of the activity with cyclohexanone Rhodococcus sp. Phi1 ? + NADP+ + H2O - ? 395181 1.14.13.22 1,2-cyclohexandione + NADPH + H+ + O2 18% of the activity with cyclohexanone Arthrobacter sp. L661 ? + NADP+ + H2O - ? 395181 1.14.13.22 1,2-cyclohexandione + NADPH + H+ + O2 7% of the activity with cyclohexanone Arthrobacter sp. BP2 ? + NADP+ + H2O - ? 395181 1.14.13.22 1,3-cyclohexandione + NADPH + H+ + O2 11% of the activity with cyclohexanone Arthrobacter sp. ? + NADP+ + H2O - ? 395188 1.14.13.22 1,3-cyclohexandione + NADPH + H+ + O2 4% of the activity with cyclohexanone Rhodococcus sp. ? + NADP+ + H2O - ? 395188 1.14.13.22 1,3-cyclohexandione + NADPH + H+ + O2 5% of the activity with cyclohexanone Arthrobacter sp. ? + NADP+ + H2O - ? 395188 1.14.13.22 1,3-cyclohexandione + NADPH + H+ + O2 4% of the activity with cyclohexanone Rhodococcus sp. TK6 ? + NADP+ + H2O - ? 395188 1.14.13.22 1,3-cyclohexandione + NADPH + H+ + O2 5% of the activity with cyclohexanone Arthrobacter sp. L661 ? + NADP+ + H2O - ? 395188 1.14.13.22 1,3-cyclohexandione + NADPH + H+ + O2 11% of the activity with cyclohexanone Arthrobacter sp. BP2 ? + NADP+ + H2O - ? 395188 1.14.13.22 1,3-cyclohexandione + NADPH + H+ + O2 4% of the activity with cyclohexanone Rhodococcus sp. Phi2 ? + NADP+ + H2O - ? 395188 1.14.13.22 1,3-dithiane + NADPH + O2 - Acinetobacter calcoaceticus (R)-1,3-dithiane-1-oxide + NADP+ + H2O - ? 375509 1.14.13.22 1,3-dithiane + NADPH + O2 - Acinetobacter calcoaceticus NCIMB 9871 (R)-1,3-dithiane-1-oxide + NADP+ + H2O - ? 375509 1.14.13.22 1,4-cyclohexandione + NADPH + H+ + O2 112% of the activity with cyclohexanone Arthrobacter sp. ? + NADP+ + H2O - ? 395195 1.14.13.22 1,4-cyclohexandione + NADPH + H+ + O2 164% of the activity with cyclohexanone Rhodococcus sp. ? + NADP+ + H2O - ? 395195 1.14.13.22 1,4-cyclohexandione + NADPH + H+ + O2 78% of the activity with cyclohexanone Arthrobacter sp. ? + NADP+ + H2O - ? 395195 1.14.13.22 1,4-cyclohexandione + NADPH + H+ + O2 90% of the activity with cyclohexanone Rhodococcus sp. ? + NADP+ + H2O - ? 395195 1.14.13.22 1,4-cyclohexandione + NADPH + H+ + O2 90% of the activity with cyclohexanone Rhodococcus sp. Phi1 ? + NADP+ + H2O - ? 395195 1.14.13.22 1,4-cyclohexandione + NADPH + H+ + O2 112% of the activity with cyclohexanone Arthrobacter sp. BP2 ? + NADP+ + H2O - ? 395195 1.14.13.22 1,4-cyclohexandione + NADPH + H+ + O2 164% of the activity with cyclohexanone Rhodococcus sp. Phi2 ? + NADP+ + H2O - ? 395195 1.14.13.22 1,4-dioxaspiro[4.5]decan-8-one + NADPH + H+ + O2 - Rhodococcus sp. HI-31 1,4,8-trioxa-spiro[4,6]undecan-9-one + NADP+ + H2O - ? 403196 1.14.13.22 1,4-dioxaspiro[4.5]decan-8-one + NADPH + O2 + H+ - Acinetobacter calcoaceticus 1,4,8-trioxaspiro[4.6]undecan-9-one + NADP+ + H2O 80% conversion at 20 h ? 403197 1.14.13.22 1,4-dioxaspiro[4.5]decan-8-one + NADPH + O2 + H+ - Acinetobacter calcoaceticus NCIMB 9871 1,4,8-trioxaspiro[4.6]undecan-9-one + NADP+ + H2O 80% conversion at 20 h ? 403197 1.14.13.22 1-oxa-2-oxocycloheptane + NADPH + O2 oxidation Xanthobacter sp. ? - ? 288485 1.14.13.22 1-phenyl-2-propanone + NADPH + O2 - Pseudomonas sp. ? - ? 288506 1.14.13.22 1-phenyl-2-propanone + NADPH + O2 - Acinetobacter sp. ? - ? 288506 1.14.13.22 1-phenyl-2-propanone + NADPH + O2 - Xanthobacter sp. ? - ? 288506 1.14.13.22 2 thioanisole + NADPH + H+ + O2 the enzyme produces both enantiomers, leading to an ee of only 16% for the (R)-sulfoxide Thermocrispum municipale (R)-thioanisole sulfoxide + (S)-thioanisole sulfoxide + 2 NADP+ + 2 H2O - ? 440547 1.14.13.22 2 thioanisole + NADPH + H+ + O2 the enzyme produces both enantiomers, leading to an ee of only 16% for the (R)-sulfoxide Thermocrispum municipale DSM 44D49 (R)-thioanisole sulfoxide + (S)-thioanisole sulfoxide + 2 NADP+ + 2 H2O - ? 440547 1.14.13.22 2,2,6-trimethylcyclohexanone + NADPH + H+ + O2 - Rhodococcus sp. HI-31 3,7,7-trimethyloxepan-2-one + NADP+ + H2O - ? 403358 1.14.13.22 2,2,6-trimethylcyclohexanone + NADPH + O2 + H+ - Acinetobacter calcoaceticus 3,7,7-trimethyloxepan-2-one + NADP+ + H2O 66% conversion at 20 h ? 403359 1.14.13.22 2,2,6-trimethylcyclohexanone + NADPH + O2 + H+ - Acinetobacter calcoaceticus NCIMB 9871 3,7,7-trimethyloxepan-2-one + NADP+ + H2O 66% conversion at 20 h ? 403359 1.14.13.22 2-(methylsulfanyl)naphthalene + NADPH + H+ + O2 - Thermocrispum municipale 2-(methanesulfinyl)naphthalene + NADP+ + H2O - ? 461951 1.14.13.22 2-(methylsulfanyl)naphthalene + NADPH + H+ + O2 - Thermocrispum municipale DSM 44069 2-(methanesulfinyl)naphthalene + NADP+ + H2O - ? 461951 1.14.13.22 2-butanone + NADPH + H+ + O2 the ratio between the products methyl propanoate and ethyl acetate was found to be about 3:7 in the absence of any cosolvent Acinetobacter calcoaceticus ethyl acetate + NADP+ + H2O - ? 440647 1.14.13.22 2-butanone + NADPH + H+ + O2 the ratio between the products methyl propanoate and ethyl acetate was found to be about 3:7 in the absence of any cosolvent. The effect of various solvents at 15% concentration is inspected. The strongest effect on regioselectivity is observed with 2-methyl-1,3-dioxolane (15%), which leads to almost exclusive production of ethyl acetate. 1,3-Dioxane and 1,4-dioxane have a more moderate influence, since about 40% of the total product is methyl propanoate. 30% methanol or ethanol as cosolvents have a negligible effect on enzyme regioselectivity Thermocrispum municipale ethyl acetate + NADP+ + H2O - ? 440647 1.14.13.22 2-butanone + NADPH + H+ + O2 the ratio between the products methyl propanoate and ethyl acetate was found to be about 3:7 in the absence of any cosolvent Acinetobacter calcoaceticus NCIMB 9871 ethyl acetate + NADP+ + H2O - ? 440647 1.14.13.22 2-butanone + NADPH + H+ + O2 the ratio between the products methyl propanoate and ethyl acetate was found to be about 3:7 in the absence of any cosolvent. The effect of various solvents at 15% concentration is inspected. The strongest effect on regioselectivity is observed with 2-methyl-1,3-dioxolane (15%), which leads to almost exclusive production of ethyl acetate. 1,3-Dioxane and 1,4-dioxane have a more moderate influence, since about 40% of the total product is methyl propanoate. 30% methanol or ethanol as cosolvents have a negligible effect on enzyme regioselectivity Thermocrispum municipale DSM 44D49 ethyl acetate + NADP+ + H2O - ? 440647 1.14.13.22 2-butanone + NADPH + H+ + O2 - Acinetobacter calcoaceticus methyl propanoate + NADP+ + H2O - ? 440648 1.14.13.22 2-butanone + NADPH + H+ + O2 the ratio between the products methyl propanoate and ethyl acetate was found to be about 3:7 in the absence of any cosolvent Acinetobacter calcoaceticus methyl propanoate + NADP+ + H2O - ? 440648 1.14.13.22 2-butanone + NADPH + H+ + O2 the ratio between the products methyl propanoate and ethyl acetate was found to be about 3:7 in the absence of any cosolvent. The effect of various solvents at 15% concentration is inspected. The strongest effect on regioselectivity is observed with 2-methyl-1,3-dioxolane (15%), which leads to almost exclusive production of ethyl acetate. 1,3-Dioxane and 1,4-dioxane have a more moderate influence, since about 40% of the total product is methyl propanoate. 30% methanol or ethanol as cosolvents have a negligible effect on enzyme regioselectivity Thermocrispum municipale methyl propanoate + NADP+ + H2O - ? 440648 1.14.13.22 2-chlorothioanisole + NADPH + H+ + O2 - Thermocrispum municipale 1-(methanesulfinyl)-2-chlorobenzene + NADP+ + H2O - ? 461965 1.14.13.22 2-chlorothioanisole + NADPH + H+ + O2 - Thermocrispum municipale DSM 44069 1-(methanesulfinyl)-2-chlorobenzene + NADP+ + H2O - ? 461965 1.14.13.22 2-hexyl-cyclopentanone + NADPH + O2 - Acinetobacter calcoaceticus ? - ? 288486 1.14.13.22 2-hexylcyclopentanone + NADPH + H+ + O2 - Rhodococcus sp. HI-31 6-hexyl-tetrahydro-pyran-2-one + NADP+ + H2O - ? 403541 1.14.13.22 2-hexylcyclopentanone + NADPH + O2 + H+ - Acinetobacter calcoaceticus 6-hexyltetrahydro-2H-pyran-2-one + NADP+ + H2O 82% conversion at 20 h ? 403542 1.14.13.22 2-hydroxycyclobutanone + NADPH + H+ + O2 67.3% of the activity with cyclohexanone Ilyonectria destructans 1-oxa-2-oxo-3-hydroxycyclopentane + NADP+ + H2O - ? 425428 1.14.13.22 2-hydroxycyclohexanone + NADPH + O2 - Pseudomonas aeruginosa 1-oxa-2-oxo-3-hydroxycycloheptane + NADP+ + H2O - ? 288502 1.14.13.22 2-hydroxycyclohexanone + NADPH + O2 - Nocardia globerula 1-oxa-2-oxo-3-hydroxycycloheptane + NADP+ + H2O - ? 288502 1.14.13.22 2-hydroxycyclohexanone + NADPH + O2 - Nocardia sp. 1-oxa-2-oxo-3-hydroxycycloheptane + NADP+ + H2O - ? 288502 1.14.13.22 2-hydroxycyclohexanone + NADPH + O2 - Acinetobacter sp. 1-oxa-2-oxo-3-hydroxycycloheptane + NADP+ + H2O - ? 288502 1.14.13.22 2-hydroxycyclohexanone + NADPH + O2 - Xanthobacter sp. 1-oxa-2-oxo-3-hydroxycycloheptane + NADP+ + H2O - ? 288502 1.14.13.22 2-hydroxycyclohexanone + NADPH + O2 no activity Xanthobacter sp. 1-oxa-2-oxo-3-hydroxycycloheptane + NADP+ + H2O - ? 288502 1.14.13.22 2-hydroxycyclohexanone + NADPH + O2 no activity Xanthobacter autotrophicus 1-oxa-2-oxo-3-hydroxycycloheptane + NADP+ + H2O - ? 288502 1.14.13.22 2-hydroxyethyl methyl sulfide + NADPH + O2 - Acinetobacter sp. 2-hydroxyethyl methyl sulfoxide + NADP+ + H2O - ? 288524 1.14.13.22 2-methyl-cyclohexanone + NADPH + H+ + O2 85% of the activity with cyclohexanone Rhodococcus sp. 1-oxa-2-oxo-3-methyl-cycloheptane + NADP+ + H2O - ? 395567 1.14.13.22 2-methyl-cyclohexanone + NADPH + H+ + O2 best substrate, 130% of the activity with cyclohexanone Rhodococcus sp. 1-oxa-2-oxo-3-methyl-cycloheptane + NADP+ + H2O - ? 395567 1.14.13.22 2-methyl-cyclohexanone + NADPH + H+ + O2 159% of the activity with cyclohexanone Rhodococcus sp. 1-oxa-2-oxo-3-methylcycloheptane + NADP+ + H2O - ? 395569 1.14.13.22 2-methyl-cyclohexanone + NADPH + H+ + O2 89% of the activity with cyclohexanone Arthrobacter sp. 1-oxa-2-oxo-3-methylcycloheptane + NADP+ + H2O - ? 395569 1.14.13.22 2-methyl-cyclohexanone + NADPH + H+ + O2 best substrate, 118% of the activity with cyclohexanone Arthrobacter sp. 1-oxa-2-oxo-3-methylcycloheptane + NADP+ + H2O - ? 395569 1.14.13.22 2-methyl-cyclohexanone + NADPH + H+ + O2 79.2% of the activity with cyclohexanone Ilyonectria destructans 1-oxa-2-oxo-3-methylcycloheptane + NADP+ + H2O - ? 395569 1.14.13.22 2-methyl-cyclohexanone + NADPH + H+ + O2 79.2% of the activity with cyclohexanone Ilyonectria destructans ATCC 11011 1-oxa-2-oxo-3-methylcycloheptane + NADP+ + H2O - ? 395569 1.14.13.22 2-methyl-cyclopentanone + NADPH + H+ + O2 81% of the activity with cyclohexanone Rhodococcus sp. 1-oxa-2-oxo-3-methyl-cyclohexane + NADP+ + H2O - ? 395570 1.14.13.22 2-methyl-cyclopentanone + NADPH + H+ + O2 best substrate, 172% of the activity with cyclohexanone Rhodococcus sp. 1-oxa-2-oxo-3-methyl-cyclohexane + NADP+ + H2O - ? 395570 1.14.13.22 2-methyl-cyclopentanone + NADPH + H+ + O2 92% of the activity with cyclohexanone Rhodococcus sp. 1-oxa-2-oxo-3-methylcyclohexane + NADP+ + H2O - ? 395571 1.14.13.22 2-methyl-cyclopentanone + NADPH + H+ + O2 98% of the activity with cyclohexanone Arthrobacter sp. 1-oxa-2-oxo-3-methylcyclohexane + NADP+ + H2O - ? 395571 1.14.13.22 2-methyl-cyclopentanone + NADPH + H+ + O2 60.5% of the activity with cyclohexanone Ilyonectria destructans 1-oxa-2-oxo-3-methylcyclohexane + NADP+ + H2O - ? 395571 1.14.13.22 2-methyl-cyclopentanone + NADPH + H+ + O2 60.5% of the activity with cyclohexanone Ilyonectria destructans ATCC 11011 1-oxa-2-oxo-3-methylcyclohexane + NADP+ + H2O - ? 395571 1.14.13.22 2-methylcyclohexanone + NADPH + O2 - Pseudomonas aeruginosa 1-oxa-2-oxo-3-methylcycloheptane + NADP+ + H2O - ? 288481 1.14.13.22 2-methylcyclohexanone + NADPH + O2 - Nocardia globerula 1-oxa-2-oxo-3-methylcycloheptane + NADP+ + H2O - ? 288481 1.14.13.22 2-methylcyclohexanone + NADPH + O2 - Nocardia sp. 1-oxa-2-oxo-3-methylcycloheptane + NADP+ + H2O - ? 288481 1.14.13.22 2-methylcyclohexanone + NADPH + O2 - Acinetobacter sp. 1-oxa-2-oxo-3-methylcycloheptane + NADP+ + H2O - ? 288481 1.14.13.22 2-methylcyclohexanone + NADPH + O2 - Xanthobacter sp. 1-oxa-2-oxo-3-methylcycloheptane + NADP+ + H2O - ? 288481 1.14.13.22 2-methylcyclohexanone + NADPH + O2 - Pseudomonas aeruginosa PA 09501 1-oxa-2-oxo-3-methylcycloheptane + NADP+ + H2O - ? 288481 1.14.13.22 2-methylcyclohexanone + NADPH + O2 + H+ - Acinetobacter calcoaceticus 7-methyloxepan-2-one + NADP+ + H2O - ? 403586 1.14.13.22 2-methylcyclohexyl boronic acid + NADPH + O2 racemic substrate Acinetobacter sp. 2-methylcyclohexanol + BO3- + NADP+ + H2O - ? 288510 1.14.13.22 2-norbornanone + NADPH + O2 - Acinetobacter sp. ? - ? 288493 1.14.13.22 2-phenyl-1-ethanal + NADPH + O2 - Pseudomonas sp. ? - ? 288507 1.14.13.22 2-phenyl-1-ethanal + NADPH + O2 - Acinetobacter sp. ? - ? 288507 1.14.13.22 2-phenyl-1-ethanal + NADPH + O2 - Xanthobacter sp. ? - ? 288507 1.14.13.22 2-phenylcyclohexanone + NADPH + H+ + O2 - Rhodococcus sp. HI-31 3-phenyloxepan-2-one + NADP+ + H2O - ? 403624 1.14.13.22 2-phenylcyclohexanone + NADPH + H+ + O2 - Acinetobacter johnsonii 1-oxa-2-oxo-3-phenylcycloheptane + NADP+ + H2O - ? 425477 1.14.13.22 2-phenylcyclohexanone + NADPH + H+ + O2 11% of the activity with cyclohexanone Ilyonectria destructans 1-oxa-2-oxo-3-phenylcycloheptane + NADP+ + H2O - ? 425477 1.14.13.22 2-phenylcyclohexanone + NADPH + O2 slight Acinetobacter sp. 1-oxa-2-oxo-3-phenylcycloheptane + NADP+ + H2O - ? 288498 1.14.13.22 2-phenylcyclohexanone + NADPH + O2 + H+ - Acinetobacter calcoaceticus 7-phenyloxepan-2-one + NADP+ + H2O 51% conversion at 20 h ? 403625 1.14.13.22 2-phenylethyl methyl sulfide + NADPH + O2 - Acinetobacter sp. 2-phenylethyl methyl sulfoxide - ? 288536 1.14.13.22 2-phenylpropyl methyl sulfide + NADPH + O2 - Acinetobacter sp. 2-phenylpropyl methyl sulfoxide - ? 288537 1.14.13.22 2-propylcyclohexanone + NADPH + O2 + H+ - Acinetobacter calcoaceticus (7S)-7-propyloxepan-2-one + NADP+ + H2O - ? 403635 1.14.13.22 2-thiacyclohexanone + NADPH + O2 substrate inactivates enzyme after a few turnovers Acinetobacter sp. 1-oxa-2-oxo-3-thiacycloheptane + NADP+ + H2O - ? 288503 1.14.13.22 3,3,5-trimethyl-cyclohexanone + NADPH + H+ + O2 - Thermocrispum municipale trimethyl-epsilon-caprolactone + NADP+ + H2O - ? 462008 1.14.13.22 3,3,5-trimethyl-cyclohexanone + NADPH + H+ + O2 - Thermocrispum municipale DSM 44069 trimethyl-epsilon-caprolactone + NADP+ + H2O - ? 462008 1.14.13.22 3,3,5-trimethylcyclohexanone + NADPH + H+ + O2 - Rhodococcus sp. HI-31 4,6,6-trimethyloxepan-2-one + 4,4,6-trimethyloxepan-2-one + NADP+ + H2O - ? 403667 1.14.13.22 3,3,5-trimethylcyclohexanone + NADPH + O2 + H+ - Acinetobacter calcoaceticus 4,6,6-trimethyloxepan-2-one + 4,4,6-trimethyloxepan-2-one + NADP+ + H2O 91% conversion at 20 h, 1/1 isomer with 98% enantiomeric excess ? 403668 1.14.13.22 3,3,5-trimethylcyclohexanone + NADPH + O2 + H+ 90% conversion efficincy, purified enzyme Acidovorax sp. CHX100 4,6,6-trimethyloxepan-2-one + 4,4,6-trimethyloxepan-2-one + NADP+ + H2O - ? 403668 1.14.13.22 3,4-dihydronaphthalen-2(1H)-one + NADPH + H+ + O2 - Rhodococcus sp. HI-31 8,9-dihydro-5H-7-oxa-benzocyclo-hepten-6-one + NADP+ + H2O - ? 403673 1.14.13.22 3,4-dihydronaphthalen-2(1H)-one + NADPH + O2 + H+ - Acinetobacter calcoaceticus 4,5-dihydro-3-benzoxepin-2(1H)-one + NADP+ + H2O more than 95% conversion one isomer ? 403674 1.14.13.22 3,5-dimethylcyclohexanone + NADPH + H+ + O2 less than 50% conversion, 90% enantiomeric excess, (-)-product Polaromonas sp. 4,6-dimethyloxepan-2-one + NADP+ + H2O - ? 425533 1.14.13.22 3-(1,3-benzodioxol-5-yl)cyclobutanone + NADPH + H+ + O2 more than 90% conversion,36% enantiomeric excess, (+)-product Polaromonas sp. 4-(1,3-benzodioxol-5-yl)dihydrofuran-2(3H)-one + NADP+ + H2O - ? 425534 1.14.13.22 3-(3,4,5-trimethoxyphenyl)cyclobutanone + NADPH + H+ + O2 less than 50% conversion, 96% enantiomeric excess, (-)-product Polaromonas sp. 4-(3,4,5-trimethoxyphenyl)dihydrofuran-2(3H)-one + NADP+ + H2O - ? 425536 1.14.13.22 3-methylcyclohexanone + NADPH + O2 + H+ - Acinetobacter calcoaceticus (4S)-4-methyloxepan-2-one + (6R)-6-methyloxepan-2-one + NADP+ + H2O - ? 403749 1.14.13.22 3-phenylcyclobutanone+ NADPH + H+ + O2 - Acinetobacter johnsonii 3-phenyloxolan-2-one + NADP+ + H2O - ? 462044 1.14.13.22 3-phenylcyclohexanone + NADPH + H+ + O2 - Acinetobacter johnsonii 1-oxa-2-oxo-4-phenylcycloheptane + NADP+ + H2O - ? 462045 1.14.13.22 3-phenylcyclopentanone + NADPH + H+ + O2 - Acinetobacter johnsonii 4-phenyloxan-2-one + NADP+ + H2O - ? 462046 1.14.13.22 3-thiacyclohexanone + NADPH + H+ + O2 - Acinetobacter sp. ? - r 451272 1.14.13.22 4,4-dimethylcyclohexanone + NADPH + H+ + O2 50-90% conversion Polaromonas sp. 5,5-dimethyloxepan-2-one + NADP+ + H2O - ? 425612 1.14.13.22 4-(3-fluorophenyl)cyclohexanone + NADPH + H+ + O2 - Acinetobacter sp. 4-(3-fluorophenyl)hexano-6-lactone + NADP+ + H2O - ? 462056 1.14.13.22 4-(3-methylphenyl)cyclohexanone + NADPH + H+ + O2 - Acinetobacter sp. 4-(3-methylphenyl)hexano-6-lactone + NADP+ + H2O - ? 462057 1.14.13.22 4-(4-chlorophenyl)cyclohexanone + NADPH + H+ + O2 - Acinetobacter sp. 4-(4-chlorophenyl)hexano-6-lactone + NADP+ + H2O - ? 462058 1.14.13.22 4-(4-fluorophenyl)cyclohexanone + NADPH + H+ + O2 - Acinetobacter sp. 4-(4-fluorophenyl)hexano-6-lactone + NADP+ + H2O - ? 462059 1.14.13.22 4-(4-methoxyhenyl)cyclohexanone + NADPH + H+ + O2 - Acinetobacter sp. 4-(4-methoxyphenyl)hexano-6-lactone + NADP+ + H2O - ? 462060 1.14.13.22 4-(4-methylphenyl)cyclohexanone + NADPH + H+ + O2 - Acinetobacter sp. 4-(4-methylphenyl)hexano-6-lactone + NADP+ + H2O - ? 462061 1.14.13.22 4-allyl-cyclohexanone + NADPH + O2 - Escherichia coli 4-allyl-hexano-6-lactone + NADP+ + H2O - ? 387415 1.14.13.22 4-bromocyclohexanone + NADPH + O2 - Escherichia coli 4-bromo-hexano-6-lactone + NADP+ + H2O - ? 387423 1.14.13.22 4-chlorocyclohexanone + NADPH + O2 - Escherichia coli 4-chloro-hexano-6-lactone + NADP+ + H2O - ? 387430 1.14.13.22 4-ethoxy-cyclohexanone + NADPH + O2 - Escherichia coli 4-ethoxy-hexano-6-lactone + NADP+ + H2O - ? 387441 1.14.13.22 4-ethyl-cyclohexanone + NADPH + O2 - Escherichia coli 4-ethyl-hexano-6-lactone + NADP+ + H2O - ? 387443 1.14.13.22 4-ethylcyclohexanone + NADPH + H+ + O2 - Acinetobacter sp. 4-ethylhexano-6-lactone + NADP+ + H2O - ? 462075 1.14.13.22 4-ethylcyclohexanone + NADPH + O2 + H+ - Acinetobacter calcoaceticus (5S)-5-ethyloxepan-2-one + NADP+ + H2O 98% enantiomeric excess ? 403829 1.14.13.22 4-ethylcyclohexanone + NADPH + O2 + H+ 95% conversion efficincy, purified enzyme Acidovorax sp. CHX100 (5S)-5-ethyloxepan-2-one + NADP+ + H2O - ? 403829 1.14.13.22 4-hydroxy-cyclohexanone + NADPH + O2 - Acinetobacter sp. 4-hydroxy-hexano-6-lactone + NADP+ + H2O - ? 386145 1.14.13.22 4-hydroxy-cyclohexanone + NADPH + O2 an enantioselective Baeyer-Villiger oxidation Acinetobacter sp. 4-hydroxy-hexano-6-lactone + NADP+ + H2O - ? 386145 1.14.13.22 4-hydroxy-cyclohexanone + NADPH + O2 low enantioselectivity Escherichia coli 4-hydroxy-hexano-6-lactone + NADP+ + H2O - ? 386145 1.14.13.22 4-hydroxy-cyclohexanone + NADPH + O2 - Acinetobacter sp. NCIMB 9871 4-hydroxy-hexano-6-lactone + NADP+ + H2O - ? 386145 1.14.13.22 4-hydroxy-cyclohexanone + NADPH + O2 an enantioselective Baeyer-Villiger oxidation Acinetobacter sp. NCIMB 9871 4-hydroxy-hexano-6-lactone + NADP+ + H2O - ? 386145 1.14.13.22 4-hydroxycyclohexanone + NADPH + O2 - Nocardia globerula 1-oxa-2-oxo-5-hydroxycycloheptane + NADP+ + H2O - ? 288501 1.14.13.22 4-hydroxycyclohexanone + NADPH + O2 - Acinetobacter sp. 1-oxa-2-oxo-5-hydroxycycloheptane + NADP+ + H2O - ? 288501 1.14.13.22 4-iodocyclohexanone + NADPH + O2 - Escherichia coli 4-iodo-hexano-6-lactone + NADP+ + H2O - ? 387484 1.14.13.22 4-methoxy-cyclohexanone + NADPH + O2 - Escherichia coli 4-methoxy-hexano-6-lactone + NADP+ + H2O - ? 387487 1.14.13.22 4-methoxythioanisole + NADPH + H+ + O2 - Thermocrispum municipale 1-(methanesulfinyl)-4-methoxybenzene + NADP+ + H2O - ? 462084 1.14.13.22 4-methoxythioanisole + NADPH + H+ + O2 - Thermocrispum municipale DSM 44069 1-(methanesulfinyl)-4-methoxybenzene + NADP+ + H2O - ? 462084 1.14.13.22 4-methyl-cyclohexanone + NADPH + O2 - Escherichia coli 4-methyl-hexano-6-lactone + NADP+ + H2O - ? 387495 1.14.13.22 4-methylcyclohexanone + NADPH + H+ + O2 - Acinetobacter johnsonii ? - ? 395894 1.14.13.22 4-methylcyclohexanone + NADPH + H+ + O2 - Acinetobacter sp. 4-methylhexano-6-lactone + NADP+ + H2O - ? 462087 1.14.13.22 4-methylcyclohexanone + NADPH + O2 - Acinetobacter calcoaceticus 1-oxa-2-oxo-5-methylcycloheptane + NADP+ + H2O - ? 288482 1.14.13.22 4-methylcyclohexanone + NADPH + O2 - Nocardia globerula 1-oxa-2-oxo-5-methylcycloheptane + NADP+ + H2O - ? 288482 1.14.13.22 4-methylcyclohexanone + NADPH + O2 - Acinetobacter sp. 1-oxa-2-oxo-5-methylcycloheptane + NADP+ + H2O - ? 288482 1.14.13.22 4-methylcyclohexanone + NADPH + O2 + H+ - Acinetobacter calcoaceticus (5S)-5-methyloxepan-2-one + NADP+ + H2O 98% enantiomeric excess ? 403890 1.14.13.22 4-methylcyclohexanone + NADPH + O2 + H+ 70% conversion efficincy, purified enzyme Acidovorax sp. CHX100 (5S)-5-methyloxepan-2-one + NADP+ + H2O - ? 403890 1.14.13.22 4-n-propyl-cyclohexanone + NADPH + O2 - Escherichia coli 4-n-propyl-hexano-6-lactone + NADP+ + H2O - ? 387515 1.14.13.22 4-pentylcyclohexanone + NADPH + H+ + O2 - Acinetobacter sp. 4-pentylhexano-6-lactone + NADP+ + H2O - ? 462103 1.14.13.22 4-phenylcyclohexanone + NADPH + H+ + O2 less than 50% conversion, 97% enantiomeric excess, (-)-product Polaromonas sp. 5-phenyloxepan-2-one + NADP+ + H2O - ? 425778 1.14.13.22 4-phenylcyclohexanone + NADPH + H+ + O2 - Acinetobacter sp. 4-phenylhexano-6-lactone + NADP+ + H2O - ? 462104 1.14.13.22 4-propylcyclohexanone + NADPH + H+ + O2 - Acinetobacter sp. 4-propylhexano-6-lactone + NADP+ + H2O - ? 462105 1.14.13.22 4-tert-butylcyclohexanone + NADPH + H+ + O2 - Rhodococcus sp. HI-31 5-t-butyl-2-oxepanone + NADP+ + H2O - ? 403973 1.14.13.22 4-tert-butylcyclohexanone + NADPH + O2 slight Acinetobacter sp. 1-oxa-2-oxo-5-tert-butylcycloheptane + NADP+ + H2O - ? 288499 1.14.13.22 4-tert-butylcyclohexanone + NADPH + O2 + H+ - Acinetobacter calcoaceticus (5S)-5-tert-butyloxepan-2-one + NADP+ + H2O 88% conversion at 20 h, 99% enantiomeric excess ? 403974 1.14.13.22 4-thiacyclohexanone + NADPH + H+ + O2 - Acinetobacter sp. ? - r 451273 1.14.13.22 4a-methyltetrahydro-1aH-naphtho[1,8a-b]oxirene-2,5(3H,6H)-dione + NADPH + O2 - Acinetobacter calcoaceticus (1R,3S,7S)-7-methyl-2,8-dioxatricyclo[5.5.0.01,3]dodecane-4,9-dione + NADP+ + H2O enantiopure product ? 387550 1.14.13.22 4a-methyltetrahydro-1aH-naphtho[1,8a-b]oxirene-2,5(3H,6H)-dione + NADPH + O2 - Acinetobacter calcoaceticus NCIMB 9871 (1R,3S,7S)-7-methyl-2,8-dioxatricyclo[5.5.0.01,3]dodecane-4,9-dione + NADP+ + H2O enantiopure product ? 387550 1.14.13.22 5-methoxy-2-methylthio-1H-benzimidazole + NADPH + H+ + O2 poor substrate for wild-type Acinetobacter calcoaceticus ? - ? 462141 1.14.13.22 acetophenone + NADPH + H+ + O2 - Acinetobacter calcoaceticus ? - ? 440998 1.14.13.22 acetophenone + NADPH + H+ + O2 - Thermocrispum municipale ? - ? 440998 1.14.13.22 allyl methyl sulfide + NADPH + O2 - Acinetobacter sp. ? - ? 288517 1.14.13.22 beta-tetralonne + NADPH + H+ + O2 25% conversion efficincy, purified enzyme Acidovorax sp. CHX100 ? + NADP+ + H2O - ? 462309 1.14.13.22 bicyclo[3.2.0]hept-2-en-6-one + NADPH + H+ + O2 - Acinetobacter calcoaceticus (1R,5S)-3-oxabicyclo-[3.3.0]oct-6-en-3-one + (1S,5R)-2-oxabicyclo-[3.3.0]oct-6-en-3-one + NADP+ + H2O - ? 426027 1.14.13.22 bicyclo[3.2.0]hept-2-en-6-one + NADPH + H+ + O2 - Acinetobacter calcoaceticus NCIMB 9871 (1R,5S)-3-oxabicyclo-[3.3.0]oct-6-en-3-one + (1S,5R)-2-oxabicyclo-[3.3.0]oct-6-en-3-one + NADP+ + H2O - ? 426027 1.14.13.22 bicyclo[3.2.0]hept-2-en-6-one + NADPH + H+ + O2 63% of the activity with cyclohexanone Ilyonectria destructans 3,3a,6,6a-tetrahydro-1H-cyclopenta[c]furan-1-one + NADP+ + H2O - ? 426028 1.14.13.22 bicyclo[3.2.0]hept-2-en-6-one + NADPH + H+ + O2 - Acinetobacter calcoaceticus ? - ? 428445 1.14.13.22 bicyclo[3.2.0]hept-2-en-6-one + NADPH + H+ + O2 the enzyme produces all four possible lactones Acinetobacter johnsonii ? - ? 428445 1.14.13.22 bicyclo[3.2.0]hept-2-en-6-one + NADPH + H+ + O2 the enzyme produces all four possible lactones Thermocrispum municipale ? - ? 428445 1.14.13.22 bicyclo[3.2.0]hept-2-en-6-one + NADPH + H+ + O2 - Acinetobacter calcoaceticus NCIMB 9871 ? - ? 428445 1.14.13.22 bicyclo[3.2.0]hept-2-en-6-one + NADPH + H+ + O2 the enzyme produces all four possible lactones Thermocrispum municipale DSM 44D49 ? - ? 428445 1.14.13.22 bicyclo[3.2.0]hept-2-en-6-one + NADPH + O2 - Acinetobacter calcoaceticus ? - ? 288535 1.14.13.22 bicyclo[3.2.0]hept-2-en-6-one + NADPH + O2 racemic substrate Acinetobacter calcoaceticus ? - ? 288535 1.14.13.22 bicyclo[3.2.0]hept-2-en-6-one + NADPH + O2 recombinant from E. coli Acinetobacter calcoaceticus ? - ? 288535 1.14.13.22 bicyclo[3.2.0]hept-2-en-6-one + NADPH + O2 recombinant in E. coli Acinetobacter calcoaceticus ? - ? 288535 1.14.13.22 butanal + NADPH + O2 - Acinetobacter sp. ? - ? 288509 1.14.13.22 cis-hex-2-enyl phenyl selenide + NADPH + O2 - Acinetobacter sp. ? - ? 288531 1.14.13.22 cuprizone + NADPH + O2 - Nocardia globerula ? - ? 288508 1.14.13.22 cuprizone + NADPH + O2 - Acinetobacter sp. ? - ? 288508 1.14.13.22 cyclobutanone + NADPH + H+ + O2 3% of the activity with cyclohexanone Rhodococcus sp. 1-oxa-2-oxo-cyclopentane + NADP+ + H2O - ? 396802 1.14.13.22 cyclobutanone + NADPH + H+ + O2 4% of the activity with cyclohexanone Arthrobacter sp. 1-oxa-2-oxo-cyclopentane + NADP+ + H2O - ? 396802 1.14.13.22 cyclobutanone + NADPH + H+ + O2 4% of the activity with cyclohexanone Rhodococcus sp. 1-oxa-2-oxo-cyclopentane + NADP+ + H2O - ? 396802 1.14.13.22 cyclobutanone + NADPH + H+ + O2 92% of the activity with cyclohexanone Arthrobacter sp. 1-oxa-2-oxo-cyclopentane + NADP+ + H2O - ? 396802 1.14.13.22 cyclobutanone + NADPH + H+ + O2 86.9% of the activity with cyclohexanone Ilyonectria destructans 1-oxa-2-oxo-cyclopentane + NADP+ + H2O - ? 396802 1.14.13.22 cyclobutanone + NADPH + H+ + O2 86.9% of the activity with cyclohexanone Ilyonectria destructans ATCC 11011 1-oxa-2-oxo-cyclopentane + NADP+ + H2O - ? 396802 1.14.13.22 cyclobutanone + NADPH + H+ + O2 65% of the activity with cyclohexanone Rhodococcus sp. dihydrofuran-2(3H)-one + NADP+ + H2O - ? 396803 1.14.13.22 cyclobutanone + NADPH + H+ + O2 - Acinetobacter calcoaceticus ? - ? 441234 1.14.13.22 cyclobutanone + NADPH + H+ + O2 - Thermocrispum municipale ? - ? 441234 1.14.13.22 cyclobutanone + NADPH + O2 - Pseudomonas aeruginosa 1-oxa-2-oxo-cyclopentane + NADP+ + H2O - ? 288483 1.14.13.22 cyclobutanone + NADPH + O2 - Nocardia globerula 1-oxa-2-oxo-cyclopentane + NADP+ + H2O - ? 288483 1.14.13.22 cyclobutanone + NADPH + O2 - Nocardia sp. 1-oxa-2-oxo-cyclopentane + NADP+ + H2O - ? 288483 1.14.13.22 cyclobutanone + NADPH + O2 - Acinetobacter sp. 1-oxa-2-oxo-cyclopentane + NADP+ + H2O - ? 288483 1.14.13.22 cyclobutanone + NADPH + O2 - Xanthobacter sp. 1-oxa-2-oxo-cyclopentane + NADP+ + H2O - ? 288483 1.14.13.22 cyclobutanone + NADPH + O2 - Exophiala jeanselmei 1-oxa-2-oxo-cyclopentane + NADP+ + H2O - ? 288483 1.14.13.22 cyclobutanone + NADPH + O2 - Pseudomonas aeruginosa PA 09501 1-oxa-2-oxo-cyclopentane + NADP+ + H2O - ? 288483 1.14.13.22 cyclobutanone + NADPH + O2 - Exophiala jeanselmei KUFI-6N 1-oxa-2-oxo-cyclopentane + NADP+ + H2O - ? 288483 1.14.13.22 cyclobutyl methyl ketone + NADPH + O2 17.5% of the activity with cyclohexanone Ilyonectria destructans ? + NADP+ + H2O - ? 426155 1.14.13.22 cyclodecanone + NADPH + H+ + O2 2% of the activity with cyclohexanone Rhodococcus sp. 1-oxa-2-oxo-cycloundecane + NADP+ + H2O - ? 396804 1.14.13.22 cyclodecanone + NADPH + H+ + O2 4% of the activity with cyclohexanone Arthrobacter sp. 1-oxa-2-oxo-cycloundecane + NADP+ + H2O - ? 396804 1.14.13.22 cyclodecanone + NADPH + H+ + O2 5% of the activity with cyclohexanone Arthrobacter sp. 1-oxa-2-oxo-cycloundecane + NADP+ + H2O - ? 396804 1.14.13.22 cyclodecanone + NADPH + H+ + O2 6% of the activity with cyclohexanone Rhodococcus sp. 1-oxa-2-oxo-cycloundecane + NADP+ + H2O - ? 396804 1.14.13.22 cyclodecanone + NADPH + O2 low activity Exophiala jeanselmei 1-oxa-2-oxocycloendecane + NADP+ + H2O - ? 288489 1.14.13.22 cycloheptanone + NADPH + H+ + O2 108% of the activity with cyclohexanone Arthrobacter sp. 1-oxa-2-oxo-cyclooctane + NADP+ + H2O - ? 396805 1.14.13.22 cycloheptanone + NADPH + H+ + O2 166% of the activity with cyclohexanone Rhodococcus sp. 1-oxa-2-oxo-cyclooctane + NADP+ + H2O - ? 396805 1.14.13.22 cycloheptanone + NADPH + H+ + O2 73% of the activity with cyclohexanone Rhodococcus sp. 1-oxa-2-oxo-cyclooctane + NADP+ + H2O - ? 396805 1.14.13.22 cycloheptanone + NADPH + H+ + O2 80% of the activity with cyclohexanone Arthrobacter sp. 1-oxa-2-oxo-cyclooctane + NADP+ + H2O - ? 396805 1.14.13.22 cycloheptanone + NADPH + H+ + O2 90% of the activity with cyclohexanone Rhodococcus sp. 1-oxa-2-oxo-cyclooctane + NADP+ + H2O - ? 396805 1.14.13.22 cycloheptanone + NADPH + H+ + O2 23.5% of the activity with cyclohexanone Ilyonectria destructans 1-oxa-2-oxo-cyclooctane + NADP+ + H2O - ? 396805 1.14.13.22 cycloheptanone + NADPH + H+ + O2 23.5% of the activity with cyclohexanone Ilyonectria destructans ATCC 11011 1-oxa-2-oxo-cyclooctane + NADP+ + H2O - ? 396805 1.14.13.22 cycloheptanone + NADPH + O2 - Pseudomonas aeruginosa 1-oxa-2-oxo-cyclooctane + NADP+ + H2O - ? 288487 1.14.13.22 cycloheptanone + NADPH + O2 - Nocardia globerula 1-oxa-2-oxo-cyclooctane + NADP+ + H2O - ? 288487 1.14.13.22 cycloheptanone + NADPH + O2 - Nocardia sp. 1-oxa-2-oxo-cyclooctane + NADP+ + H2O - ? 288487 1.14.13.22 cycloheptanone + NADPH + O2 - Acinetobacter sp. 1-oxa-2-oxo-cyclooctane + NADP+ + H2O - ? 288487 1.14.13.22 cycloheptanone + NADPH + O2 - Xanthobacter sp. 1-oxa-2-oxo-cyclooctane + NADP+ + H2O - ? 288487 1.14.13.22 cycloheptanone + NADPH + O2 - Exophiala jeanselmei 1-oxa-2-oxo-cyclooctane + NADP+ + H2O - ? 288487 1.14.13.22 cycloheptanone + NADPH + O2 - Pseudomonas aeruginosa PA 09501 1-oxa-2-oxo-cyclooctane + NADP+ + H2O - ? 288487 1.14.13.22 cycloheptanone + NADPH + O2 - Exophiala jeanselmei KUFI-6N 1-oxa-2-oxo-cyclooctane + NADP+ + H2O - ? 288487 1.14.13.22 cyclohexan-1,2-dione + NADPH + O2 - Nocardia globerula 1-oxa-2,3-dioxo-cycloheptane + NADP+ + H2O - ? 288500 1.14.13.22 cyclohexan-1,2-dione + NADPH + O2 - Acinetobacter sp. 1-oxa-2,3-dioxo-cycloheptane + NADP+ + H2O - ? 288500 1.14.13.22 cyclohexan-1,2-dione + NADPH + O2 - Xanthobacter sp. 1-oxa-2,3-dioxo-cycloheptane + NADP+ + H2O - ? 288500 1.14.13.22 cyclohexan-1,4-dione + NADPH + O2 - Acinetobacter sp. 1-oxa-2,5-dioxo-cycloheptane + NADP+ + H2O - ? 288497 1.14.13.22 cyclohexan-1,4-dione + NADPH + O2 - Xanthobacter sp. 1-oxa-2,5-dioxo-cycloheptane + NADP+ + H2O - ? 288497 1.14.13.22 cyclohexanone + NADPH + H+ + O2 - Acinetobacter calcoaceticus epsilon-caprolactone + NADP+ + H2O - ? 394811 1.14.13.22 cyclohexanone + NADPH + H+ + O2 - Arthrobacter sp. epsilon-caprolactone + NADP+ + H2O - ? 394811 1.14.13.22 cyclohexanone + NADPH + H+ + O2 - Rhodococcus sp. epsilon-caprolactone + NADP+ + H2O - ? 394811 1.14.13.22 cyclohexanone + NADPH + H+ + O2 best substrate Ilyonectria destructans epsilon-caprolactone + NADP+ + H2O - ? 394811 1.14.13.22 cyclohexanone + NADPH + H+ + O2 an asymmetric Baeyer-Villiger biooxidation, overview Arthrobacter sp. epsilon-caprolactone + NADP+ + H2O - ? 394811 1.14.13.22 cyclohexanone + NADPH + H+ + O2 an asymmetric Baeyer-Villiger biooxidation, overview Rhodococcus sp. epsilon-caprolactone + NADP+ + H2O - ? 394811 1.14.13.22 cyclohexanone + NADPH + H+ + O2 best substrate, an asymmetric Baeyer-Villiger biooxidation, overview Arthrobacter sp. epsilon-caprolactone + NADP+ + H2O - ? 394811 1.14.13.22 cyclohexanone + NADPH + H+ + O2 best substrate, an asymmetric Baeyer-Villiger biooxidation, overview Rhodococcus sp. epsilon-caprolactone + NADP+ + H2O - ? 394811 1.14.13.22 cyclohexanone + NADPH + H+ + O2 - Acinetobacter calcoaceticus NCIMB 9871 epsilon-caprolactone + NADP+ + H2O - ? 394811 1.14.13.22 cyclohexanone + NADPH + H+ + O2 - Rhodococcus sp. TK6 epsilon-caprolactone + NADP+ + H2O - ? 394811 1.14.13.22 cyclohexanone + NADPH + H+ + O2 best substrate, an asymmetric Baeyer-Villiger biooxidation, overview Rhodococcus sp. TK6 epsilon-caprolactone + NADP+ + H2O - ? 394811 1.14.13.22 cyclohexanone + NADPH + H+ + O2 - Rhodococcus sp. Phi1 epsilon-caprolactone + NADP+ + H2O - ? 394811 1.14.13.22 cyclohexanone + NADPH + H+ + O2 an asymmetric Baeyer-Villiger biooxidation, overview Rhodococcus sp. Phi1 epsilon-caprolactone + NADP+ + H2O - ? 394811 1.14.13.22 cyclohexanone + NADPH + H+ + O2 - Arthrobacter sp. L661 epsilon-caprolactone + NADP+ + H2O - ? 394811 1.14.13.22 cyclohexanone + NADPH + H+ + O2 best substrate, an asymmetric Baeyer-Villiger biooxidation, overview Arthrobacter sp. L661 epsilon-caprolactone + NADP+ + H2O - ? 394811 1.14.13.22 cyclohexanone + NADPH + H+ + O2 - Arthrobacter sp. BP2 epsilon-caprolactone + NADP+ + H2O - ? 394811 1.14.13.22 cyclohexanone + NADPH + H+ + O2 an asymmetric Baeyer-Villiger biooxidation, overview Arthrobacter sp. BP2 epsilon-caprolactone + NADP+ + H2O - ? 394811 1.14.13.22 cyclohexanone + NADPH + H+ + O2 - Rhodococcus sp. Phi2 epsilon-caprolactone + NADP+ + H2O - ? 394811 1.14.13.22 cyclohexanone + NADPH + H+ + O2 an asymmetric Baeyer-Villiger biooxidation, overview Rhodococcus sp. Phi2 epsilon-caprolactone + NADP+ + H2O - ? 394811 1.14.13.22 cyclohexanone + NADPH + H+ + O2 best substrate Ilyonectria destructans ATCC 11011 epsilon-caprolactone + NADP+ + H2O - ? 394811 1.14.13.22 cyclohexanone + NADPH + H+ + O2 - Acinetobacter calcoaceticus hexano-6-lactone + NADP+ + H2O - ? 402560 1.14.13.22 cyclohexanone + NADPH + H+ + O2 - Rhodococcus sp. HI-31 hexano-6-lactone + NADP+ + H2O - ? 402560 1.14.13.22 cyclohexanone + NADPH + H+ + O2 - Acinetobacter johnsonii hexano-6-lactone + NADP+ + H2O - ? 402560 1.14.13.22 cyclohexanone + NADPH + H+ + O2 - Thermocrispum municipale hexano-6-lactone + NADP+ + H2O - ? 402560 1.14.13.22 cyclohexanone + NADPH + H+ + O2 - Acinetobacter sp. hexano-6-lactone + NADP+ + H2O - ? 402560 1.14.13.22 cyclohexanone + NADPH + H+ + O2 100% conversion efficincy, purified enzyme Acidovorax sp. CHX100 hexano-6-lactone + NADP+ + H2O - ? 402560 1.14.13.22 cyclohexanone + NADPH + H+ + O2 - Acinetobacter calcoaceticus NCIMB 9871 hexano-6-lactone + NADP+ + H2O - ? 402560 1.14.13.22 cyclohexanone + NADPH + H+ + O2 - Thermocrispum municipale DSM 44D49 hexano-6-lactone + NADP+ + H2O - ? 402560 1.14.13.22 cyclohexanone + NADPH + O2 - Arthrobacter sp. 6-hexanolide + NADP+ + H2O - ? 288480 1.14.13.22 cyclohexanone + NADPH + O2 - Nocardia globerula 6-hexanolide + NADP+ + H2O - ? 288480 1.14.13.22 cyclohexanone + NADPH + O2 - Acinetobacter sp. 6-hexanolide + NADP+ + H2O - ? 288480 1.14.13.22 cyclohexanone + NADPH + O2 - Xanthobacter sp. 6-hexanolide + NADP+ + H2O - ? 288480 1.14.13.22 cyclohexanone + NADPH + O2 - Acinetobacter calcoaceticus 6-hexanolide + NADP+ + H2O product: epsilon-caprolactone i.e. 1-oxa-2-oxocycloheptane ? 288480 1.14.13.22 cyclohexanone + NADPH + O2 - Acinetobacter sp. 6-hexanolide + NADP+ + H2O product: epsilon-caprolactone i.e. 1-oxa-2-oxocycloheptane ? 288480 1.14.13.22 cyclohexanone + NADPH + O2 - Xanthobacter sp. 6-hexanolide + NADP+ + H2O product: epsilon-caprolactone i.e. 1-oxa-2-oxocycloheptane ? 288480 1.14.13.22 cyclohexanone + NADPH + O2 - Xanthobacter autotrophicus 6-hexanolide + NADP+ + H2O product: epsilon-caprolactone i.e. 1-oxa-2-oxocycloheptane ? 288480 1.14.13.22 cyclohexanone + NADPH + O2 - Exophiala jeanselmei 6-hexanolide + NADP+ + H2O product: epsilon-caprolactone i.e. 1-oxa-2-oxocycloheptane ? 288480 1.14.13.22 cyclohexanone + NADPH + O2 activity limited to cyclic ketones Acinetobacter sp. 6-hexanolide + NADP+ + H2O product: epsilon-caprolactone i.e. 1-oxa-2-oxocycloheptane ? 288480 1.14.13.22 cyclohexanone + NADPH + O2 - Exophiala jeanselmei KUFI-6N 6-hexanolide + NADP+ + H2O product: epsilon-caprolactone i.e. 1-oxa-2-oxocycloheptane ? 288480 1.14.13.22 cyclohexanone + NADPH + O2 - Arthrobacter sp. CA1 6-hexanolide + NADP+ + H2O - ? 288480 1.14.13.22 cyclohexanone + NADPH + O2 - Acinetobacter calcoaceticus 1-oxa-2-oxocycloheptane + NADP+ + H2O - ? 288570 1.14.13.22 cyclohexanone + NADPH + O2 - Xanthobacter sp. 1-oxa-2-oxocycloheptane + NADP+ + H2O - ? 288570 1.14.13.22 cyclohexanone + NADPH + O2 enzyme plays an important role in degradation of keto-compounds by microorganisms Acinetobacter sp. 1-oxa-2-oxocycloheptane + NADP+ + H2O - ? 288570 1.14.13.22 cyclohexanone + NADPH + O2 pathway Arthrobacter sp. 1-oxa-2-oxocycloheptane + NADP+ + H2O - ? 288570 1.14.13.22 cyclohexanone + NADPH + O2 depending on inducing growth substrate Xanthobacter sp. 1-oxa-2-oxocycloheptane + NADP+ + H2O - ? 288570 1.14.13.22 cyclohexanone + NADPH + O2 depending on inducing growth substrate Xanthobacter autotrophicus 1-oxa-2-oxocycloheptane + NADP+ + H2O - ? 288570 1.14.13.22 cyclohexanone + NADPH + O2 pathway Arthrobacter sp. CA1 1-oxa-2-oxocycloheptane + NADP+ + H2O - ? 288570 1.14.13.22 cyclohexanone + NADPH + O2 - Acinetobacter calcoaceticus epsilon-caprolactone + NADP+ + H2O - ? 375099 1.14.13.22 cyclohexanone + NADPH + O2 initial step of the degradation of cyclohexanone to adipic acid Rhodococcus ruber epsilon-caprolactone + NADP+ + H2O - ? 375099 1.14.13.22 cyclohexanone + NADPH + O2 - Acinetobacter calcoaceticus NCIMB 9871 epsilon-caprolactone + NADP+ + H2O - ? 375099 1.14.13.22 cyclohexanone + NADPH + O2 initial step of the degradation of cyclohexanone to adipic acid Rhodococcus ruber Phi 2 epsilon-caprolactone + NADP+ + H2O - ? 375099 1.14.13.22 cyclohexanone + NADPH + O2 - Escherichia coli hexano-6-lactone + NADP+ + H2O - ? 375100 1.14.13.22 cyclohexanone + NADPH + O2 - Acinetobacter calcoaceticus hexano-6-lactone + NADP+ + H2O - ? 375100 1.14.13.22 cyclohexanone + NADPH + O2 - Acinetobacter sp. hexano-6-lactone + NADP+ + H2O - ? 375100 1.14.13.22 cyclohexanone + NADPH + O2 - Rhodococcus pyridinivorans hexano-6-lactone + NADP+ + H2O - ? 375100 1.14.13.22 cyclohexanone + NADPH + O2 - Arthrobacter sp. hexano-6-lactone + NADP+ + H2O - ? 375100 1.14.13.22 cyclohexanone + NADPH + O2 - Rhodococcus ruber hexano-6-lactone + NADP+ + H2O - ? 375100 1.14.13.22 cyclohexanone + NADPH + O2 - Acinetobacter calcoaceticus NCIMB 9871 hexano-6-lactone + NADP+ + H2O - ? 375100 1.14.13.22 cyclohexanone + NADPH + O2 - Acinetobacter sp. NCIMB 9871 hexano-6-lactone + NADP+ + H2O - ? 375100 1.14.13.22 cyclohexanone + NADPH + O2 - Rhodococcus ruber Phi 2 hexano-6-lactone + NADP+ + H2O - ? 375100 1.14.13.22 cyclohexanone + NADPH + O2 - Rhodococcus pyridinivorans Phi 1 hexano-6-lactone + NADP+ + H2O - ? 375100 1.14.13.22 cyclohexanone + NADPH + O2 - Arthrobacter sp. BP2 hexano-6-lactone + NADP+ + H2O - ? 375100 1.14.13.22 cyclohexyl methyl ketone + NADPH + O2 15.7% of the activity with cyclohexanone Ilyonectria destructans ? + NADP+ + H2O - ? 426162 1.14.13.22 cyclohexyl methyl sulfide + NADPH + O2 - Acinetobacter sp. cyclohexyl methyl sulfoxide + NADP+ + H2O - ? 288526 1.14.13.22 cyclooctanone + NADPH + H+ + O2 17% of the activity with cyclohexanone Rhodococcus sp. 1-oxa-2-oxo-cyclononane + NADP+ + H2O - ? 396810 1.14.13.22 cyclooctanone + NADPH + H+ + O2 18% of the activity with cyclohexanone Arthrobacter sp. 1-oxa-2-oxo-cyclononane + NADP+ + H2O - ? 396810 1.14.13.22 cyclooctanone + NADPH + H+ + O2 23% of the activity with cyclohexanone Rhodococcus sp. 1-oxa-2-oxo-cyclononane + NADP+ + H2O - ? 396810 1.14.13.22 cyclooctanone + NADPH + H+ + O2 4% of the activity with cyclohexanone Rhodococcus sp. 1-oxa-2-oxo-cyclononane + NADP+ + H2O - ? 396810 1.14.13.22 cyclooctanone + NADPH + H+ + O2 42% of the activity with cyclohexanone Arthrobacter sp. 1-oxa-2-oxo-cyclononane + NADP+ + H2O - ? 396810 1.14.13.22 cyclooctanone + NADPH + H+ + O2 3.1% of the activity with cyclohexanone Ilyonectria destructans 1-oxa-2-oxo-cyclononane + NADP+ + H2O - ? 396810 1.14.13.22 cyclooctanone + NADPH + O2 - Pseudomonas aeruginosa 1-oxa-2-oxo-cyclononane + NADP+ + H2O - ? 288488 1.14.13.22 cyclooctanone + NADPH + O2 - Nocardia globerula 1-oxa-2-oxo-cyclononane + NADP+ + H2O - ? 288488 1.14.13.22 cyclooctanone + NADPH + O2 - Nocardia sp. 1-oxa-2-oxo-cyclononane + NADP+ + H2O - ? 288488 1.14.13.22 cyclooctanone + NADPH + O2 - Acinetobacter sp. 1-oxa-2-oxo-cyclononane + NADP+ + H2O - ? 288488 1.14.13.22 cyclooctanone + NADPH + O2 - Exophiala jeanselmei 1-oxa-2-oxo-cyclononane + NADP+ + H2O - ? 288488 1.14.13.22 cyclooctanone + NADPH + O2 low activity Xanthobacter sp. 1-oxa-2-oxo-cyclononane + NADP+ + H2O - ? 288488 1.14.13.22 cyclooctanone + NADPH + O2 - Pseudomonas aeruginosa PA 09501 1-oxa-2-oxo-cyclononane + NADP+ + H2O - ? 288488 1.14.13.22 cyclooctanone + NADPH + O2 - Exophiala jeanselmei KUFI-6N 1-oxa-2-oxo-cyclononane + NADP+ + H2O - ? 288488 1.14.13.22 cyclopentanone + NADPH + H+ + O2 37% of the activity with cyclohexanone Rhodococcus sp. 1-oxa-2-oxo-cyclohexane + NADP+ + H2O - ? 396811 1.14.13.22 cyclopentanone + NADPH + H+ + O2 42% of the activity with cyclohexanone Arthrobacter sp. 1-oxa-2-oxo-cyclohexane + NADP+ + H2O - ? 396811 1.14.13.22 cyclopentanone + NADPH + H+ + O2 48% of the activity with cyclohexanone Rhodococcus sp. 1-oxa-2-oxo-cyclohexane + NADP+ + H2O - ? 396811 1.14.13.22 cyclopentanone + NADPH + H+ + O2 65% of the activity with cyclohexanone Rhodococcus sp. 1-oxa-2-oxo-cyclohexane + NADP+ + H2O - ? 396811 1.14.13.22 cyclopentanone + NADPH + H+ + O2 95% of the activity with cyclohexanone Arthrobacter sp. 1-oxa-2-oxo-cyclohexane + NADP+ + H2O - ? 396811 1.14.13.22 cyclopentanone + NADPH + H+ + O2 11.3% of the activity with cyclohexanone Ilyonectria destructans 1-oxa-2-oxo-cyclohexane + NADP+ + H2O - ? 396811 1.14.13.22 cyclopentanone + NADPH + H+ + O2 100% conversion efficincy, purified enzyme Acidovorax sp. CHX100 1-oxa-2-oxo-cyclohexane + NADP+ + H2O - ? 396811 1.14.13.22 cyclopentanone + NADPH + H+ + O2 - Acinetobacter calcoaceticus ? - ? 396813 1.14.13.22 cyclopentanone + NADPH + H+ + O2 - Thermocrispum municipale ? - ? 396813 1.14.13.22 cyclopentanone + NADPH + H+ + O2 - Acinetobacter calcoaceticus NCIMB 9871 ? - ? 396813 1.14.13.22 cyclopentanone + NADPH + H+ + O2 - Thermocrispum municipale DSM 44D49 ? - ? 396813 1.14.13.22 cyclopentanone + NADPH + O2 - Pseudomonas aeruginosa 1-oxa-2-oxo-cyclohexane + NADP+ + H2O - ? 288484 1.14.13.22 cyclopentanone + NADPH + O2 - Nocardia globerula 1-oxa-2-oxo-cyclohexane + NADP+ + H2O - ? 288484 1.14.13.22 cyclopentanone + NADPH + O2 - Nocardia sp. 1-oxa-2-oxo-cyclohexane + NADP+ + H2O - ? 288484 1.14.13.22 cyclopentanone + NADPH + O2 - Acinetobacter sp. 1-oxa-2-oxo-cyclohexane + NADP+ + H2O - ? 288484 1.14.13.22 cyclopentanone + NADPH + O2 - Xanthobacter sp. 1-oxa-2-oxo-cyclohexane + NADP+ + H2O - ? 288484 1.14.13.22 cyclopentanone + NADPH + O2 - Exophiala jeanselmei 1-oxa-2-oxo-cyclohexane + NADP+ + H2O - ? 288484 1.14.13.22 cyclopentanone + NADPH + O2 - Pseudomonas aeruginosa PA 09501 1-oxa-2-oxo-cyclohexane + NADP+ + H2O - ? 288484 1.14.13.22 cyclopentanone + NADPH + O2 - Exophiala jeanselmei KUFI-6N 1-oxa-2-oxo-cyclohexane + NADP+ + H2O - ? 288484 1.14.13.22 cyclopentyl methyl sulfide + NADPH + O2 - Acinetobacter sp. cyclopentyl methyl sulfoxide + NADP+ + H2O - ? 288525 1.14.13.22 D-fenchone + NADPH + O2 - Acinetobacter sp. ? - ? 288494 1.14.13.22 delta-thiovalerolactone + NADPH + O2 substrate inactivates enzyme after a few turnovers Acinetobacter sp. ? - ir 288538 1.14.13.22 dihydrocarvone + NADPH + O2 - Acinetobacter sp. ? - ? 288492 1.14.13.22 dithiane + NADPH + H+ + O2 recombinant enzyme in E. coli or Saccharomyces cerevisiae Acinetobacter sp. (R)-dithiane sulfoxide + NADP+ + H2O - ? 370254 1.14.13.22 epsilon-thiocaprolactone + NADPH + O2 substrate inactivates enzyme after a few turnovers Acinetobacter sp. ? - ir 288539 1.14.13.22 ethyl 4-oxocyclohexanecarboxylate + NADPH + H+ + O2 less than 50% conversion, 98% enantiomeric excess, (-)-product Polaromonas sp. ethyl 7-oxooxepane-4-carboxylate + NADP+ + H2O - ? 426385 1.14.13.22 ethyl p-tolyl sulfide + NADPH + O2 - Acinetobacter sp. (S)-ethyl p-tolyl sulfoxide + NADP+ + H2O - ? 288515 1.14.13.22 ethylene monothiocarbonate + NADPH + O2 substrate inactivates enzyme after a few turnovers Acinetobacter sp. ? - ? 288505 1.14.13.22 ethylene monothiocarbonate + NADPH + O2 substrate inactivates enzyme after a few turnovers Acinetobacter sp. ? - ir 288505 1.14.13.22 gamma-thiobutyrolactone + NADPH + O2 substrate inactivates enzyme after a few turnovers Acinetobacter sp. ? - ir 288540 1.14.13.22 iodide + NADPH + O2 - Acinetobacter sp. ? - ? 288534 1.14.13.22 isopropyl methyl sulfide + NADPH + O2 - Acinetobacter sp. ? - ? 288520 1.14.13.22 methyl phenyl sulfide + NADPH + H+ + O2 - Acinetobacter sp. (R)-methyl phenyl sulfoxide + NADP+ + H2O - ? 288518 1.14.13.22 methyl phenyl sulfide + NADPH + H+ + O2 recombinant from E. coli Acinetobacter calcoaceticus (R)-methyl phenyl sulfoxide + NADP+ + H2O - ? 288518 1.14.13.22 methyl phenyl sulfide + NADPH + H+ + O2 recombinant in E. coli Acinetobacter calcoaceticus (R)-methyl phenyl sulfoxide + NADP+ + H2O - ? 288518 1.14.13.22 methyl phenyl sulfide + NADPH + H+ + O2 recombinant enzyme in E. coli or Saccharomyces cerevisiae Acinetobacter sp. (R)-methyl phenyl sulfoxide + NADP+ + H2O - ? 288518 1.14.13.22 methyl phenyl sulfoxide + NADPH + H+ + O2 55% conversion efficincy, purified enzyme Acidovorax sp. CHX100 ? + NADP+ + H2O - ? 462713 1.14.13.22 additional information no activity towards straight-chain alkanones Pseudomonas sp. ? - ? 89 1.14.13.22 additional information no activity towards straight-chain alkanones Xanthobacter sp. ? - ? 89 1.14.13.22 additional information absolutely specific for NADPH as electron donor Acinetobacter sp. ? - ? 89 1.14.13.22 additional information absolutely specific for NADPH as electron donor Xanthobacter sp. ? - ? 89 1.14.13.22 additional information peroxide-like oxidation catalyzed Acinetobacter sp. ? - ? 89 1.14.13.22 additional information active with diverse alkyl aryl sulfides, dialkyl sulfides and dialkyldisulfides Acinetobacter sp. ? - ? 89 1.14.13.22 additional information high enantioselectivity in oxidation of sulfides Acinetobacter sp. ? - ? 89 1.14.13.22 additional information active with benzyl alkyl sulfides with alkyl groups from methyl to hexyl and para-alkylbenzyl groups from methyl to butyl Acinetobacter sp. ? - ? 89 1.14.13.22 additional information oxidation of propargylic and allylic selenides Acinetobacter sp. ? - ? 89 1.14.13.22 additional information ability to convert aryl and alkyl boronic acids into phenols and alcohols, racemic 2-methylcyclohexyl boronic acid is processed to 2-methylcyclohexanol Acinetobacter sp. ? - ? 89 1.14.13.22 additional information production of optically pure sulfoxides by biotransformation in whole cell systems of several sulfides, dithianes and dithiolanes Acinetobacter sp. ? - ? 89 1.14.13.22 additional information inductive growth on cyclohexanol, addition of cyclohexanone Acinetobacter calcoaceticus ? - ? 89 1.14.13.22 additional information also catalyze the oxidation of several more secondary amines Acinetobacter calcoaceticus ? - ? 89 1.14.13.22 additional information also oxidizes a large variety of cyclic and linear ketones Rhodococcus pyridinivorans ? - ? 89 1.14.13.22 additional information also oxidizes a large variety of cyclic and linear ketones Arthrobacter sp. ? - ? 89 1.14.13.22 additional information also oxidizes a large variety of cyclic and linear ketones Rhodococcus ruber ? - ? 89 1.14.13.22 additional information can catalyze the asymmetric sulfoxidation of numerous alkyl aryl sulfides, dialkyl sulfides, 1,3-dithioacetals, organic cyclic sulfites, and the oxidation alkyl aryl amines Acinetobacter calcoaceticus ? - ? 89 1.14.13.22 additional information Baeyer–Villiger oxidation of racemic bicyclic diketones such as the Wieland–Miescher and the Hajos–Parrish diketones and of some of their derivatives to the correspondent lactones in a highly regio- and enantioselective manner, overview Acinetobacter calcoaceticus ? - ? 89 1.14.13.22 additional information substrate specificity and enantioselectivity of wild-type and mutant enzymes, overview Acinetobacter sp. ? - ? 89 1.14.13.22 additional information substrate specificity and enantioselectivity, overview, the enzyme catalyzes the Baeyer-Villiger oxidations of prochiral 4-substituted ketones, e.g. 4,4-disubstituted cyclohexanones, to the corresponding lactones, configuration of lactone products, 4-tert-butylcyclohexanone is a poor substrate for wild-type and mutant enzymes, no activity with 4-hydroxy-4-phenylcyclohexanone of wild-type enzyme and mutant F432S, 4-tert-butylcyclohexanone is a poor substrate Escherichia coli ? - ? 89 1.14.13.22 additional information the enzyme catalyses the NADPH-dependent enantioselective oxidation of ketones and of several heteroatoms such as nitrogen, sulfur, phosphorous and selenium present in organic compounds Acinetobacter calcoaceticus ? - ? 89 1.14.13.22 additional information no activity with 1,2-cyclohexandione Rhodococcus sp. ? - ? 89 1.14.13.22 additional information no activity with 1,3-cyclohexandione Rhodococcus sp. ? - ? 89 1.14.13.22 additional information no activity with cyclodecanone Rhodococcus sp. ? - ? 89 1.14.13.22 additional information substrate specificity of the recombinant His-tagged enzyme, overview Arthrobacter sp. ? - ? 89 1.14.13.22 additional information enzyme shows excellent stereodiscrimination of 2-substituted cyclic ketones. The expression system exhibits no activity with ethene or cis-1,2-dichloroethene as substrates under the tested conditions Polaromonas sp. ? - ? 89 1.14.13.22 additional information Baeyer–Villiger oxidation of racemic bicyclic diketones such as the Wieland–Miescher and the Hajos–Parrish diketones and of some of their derivatives to the correspondent lactones in a highly regio- and enantioselective manner, overview Acinetobacter calcoaceticus NCIMB 9871 ? - ? 89 1.14.13.22 additional information also catalyze the oxidation of several more secondary amines Acinetobacter calcoaceticus NCIMB 9871 ? - ? 89 1.14.13.22 additional information can catalyze the asymmetric sulfoxidation of numerous alkyl aryl sulfides, dialkyl sulfides, 1,3-dithioacetals, organic cyclic sulfites, and the oxidation alkyl aryl amines Acinetobacter calcoaceticus NCIMB 9871 ? - ? 89 1.14.13.22 additional information no activity with cyclodecanone Rhodococcus sp. TK6 ? - ? 89 1.14.13.22 additional information substrate specificity and enantioselectivity of wild-type and mutant enzymes, overview Acinetobacter sp. NCIMB 9871 ? - ? 89 1.14.13.22 additional information no activity with 1,3-cyclohexandione Rhodococcus sp. Phi1 ? - ? 89 1.14.13.22 additional information also oxidizes a large variety of cyclic and linear ketones Rhodococcus ruber Phi 2 ? - ? 89 1.14.13.22 additional information substrate specificity of the recombinant His-tagged enzyme, overview Arthrobacter sp. L661 ? - ? 89 1.14.13.22 additional information also oxidizes a large variety of cyclic and linear ketones Rhodococcus pyridinivorans Phi 1 ? - ? 89 1.14.13.22 additional information also oxidizes a large variety of cyclic and linear ketones Arthrobacter sp. BP2 ? - ? 89 1.14.13.22 additional information no activity with 1,2-cyclohexandione Rhodococcus sp. Phi2 ? - ? 89 1.14.13.22 n-butyl methyl sulfide + NADPH + O2 recombinant enzyme in E. coli or Saccharomyces cerevisiae Acinetobacter sp. ? - ? 370253 1.14.13.22 n-butylboronic acid + NADPH + O2 - Acinetobacter sp. n-butanol + BO3- + NADP+ + H2O - ? 288512 1.14.13.22 N-methylbenzylamine + NADPH + O2 - Acinetobacter calcoaceticus N-benzyl-N-methylhydroxylamine + NADP+ + H2O - ? 377265 1.14.13.22 N-methylbenzylamine + NADPH + O2 - Acinetobacter calcoaceticus NCIMB 9871 N-benzyl-N-methylhydroxylamine + NADP+ + H2O - ? 377265 1.14.13.22 n-octylboronic acid + NADPH + O2 - Acinetobacter sp. n-octanol + BO3- + NADP+ + H2O - ? 288513 1.14.13.22 norcamphor + NADPH + O2 - Nocardia globerula ? - ? 288490 1.14.13.22 norcamphor + NADPH + O2 - Acinetobacter sp. ? - ? 288490 1.14.13.22 norcamphor + NADPH + O2 74.8% of the activity with cyclohexanone Ilyonectria destructans ? + NADP+ + H2O - ? 426854 1.14.13.22 octahydronaphthalen-1(2H)-one + NADPH + H+ + O2 - Rhodococcus sp. HI-31 octahydro-benzo[b]oxepin-2-one + octahydro-benzo[c]oxepin-1-one + NADP+ + H2O - ? 406229 1.14.13.22 octahydronaphthalen-1(2H)-one + NADPH + O2 + H+ - Acinetobacter calcoaceticus octahydro-1-benzoxepin-2(3H)-one + octahydro-2-benzoxepin-1(3H)-one + NADP+ + H2O 100% conversion two isomers octahydro-1-benzoxepin-2(3H)-one + octahydro-2-benzoxepin-1(3H)-one with ratio 2/1 ? 406230 1.14.13.22 octahydronaphthalen-2(1H)-one + NADPH + H+ + O2 - Rhodococcus sp. HI-31 cis-octahydro-benzo[c]oxepin-3-one + trans-octahydro-benzo[c]oxepin-3-one + cis-octahydro-7-oxa-benzocyclohepten-6-one + NADP+ + H2O - ? 406231 1.14.13.22 octahydronaphthalen-2(1H)-one + NADPH + O2 + H+ - Acinetobacter calcoaceticus octahydro-3-benzoxepin-2(1H)-one + octahydro-2-benzoxepin-3(1H)-one + NADP+ + H2O 66% conversion at 20 h, octahydro-2-benzoxepin-3(1H)-one is the major product ? 406232 1.14.13.22 octyl methyl sulfide + NADPH + O2 - Acinetobacter sp. ? - ? 288519 1.14.13.22 omeprazole sulfide + NADPH + H+ + O2 no substrae for wild-type Acinetobacter calcoaceticus (S)-omeprazole + NADP+ + H2O - ? 462870 1.14.13.22 phenyl allyl selenide + NADPH + O2 - Acinetobacter sp. ? - ? 288529 1.14.13.22 phenyl allyl sulfide + NADPH + O2 - Acinetobacter sp. ? - ? 288516 1.14.13.22 phenyl methyl selenide + NADPH + O2 - Acinetobacter sp. ? - ? 288528 1.14.13.22 phenyl propargyl selenide + NADPH + O2 - Acinetobacter sp. ? - ? 288530 1.14.13.22 phenylacetone + NADPH + H+ + O2 - Acinetobacter calcoaceticus ? - ? 441866 1.14.13.22 phenylacetone + NADPH + H+ + O2 - Thermocrispum municipale ? - ? 441866 1.14.13.22 phenylboronic acid + NADPH + O2 - Acinetobacter sp. phenol + BO3- + NADP+ + H2O - ? 288511 1.14.13.22 pyrmetazole + NADPH + H+ + O2 - Acinetobacter sp. pyrmetazole (S)-sulfoxide + NADP+ + H2O - ? 462935 1.14.13.22 S-gamma-thiobutyrolactone + NADPH + O2 substrate irreversibly inactivates enzyme after a few turnovers Acinetobacter sp. ? - ? 288504 1.14.13.22 syn-7-benzyloxymethyl-2-norbonen-5-one + NADPH + O2 - Acinetobacter sp. ? - ? 288496 1.14.13.22 tert-butyl ethyl sulfide + NADPH + O2 low activity Acinetobacter sp. ? - ? 288522 1.14.13.22 tert-butyl methyl sulfide + NADPH + O2 - Acinetobacter sp. ? - ? 288521 1.14.13.22 tert-butyl methyl sulfide + NADPH + O2 recombinant enzyme in E. coli or Saccharomyces cerevisiae Acinetobacter sp. ? - ? 288521 1.14.13.22 tert-butyl vinyl sulfide + NADPH + O2 - Acinetobacter sp. ? - ? 288523 1.14.13.22 thiane + NADPH + O2 - Acinetobacter sp. ? - ? 288514 1.14.13.22 thiane sulfoxide + NADPH + O2 - Acinetobacter sp. ? - ? 288527 1.14.13.22 thioanisole + NADPH + H+ + O2 - Acinetobacter calcoaceticus ? - ? 398417 1.14.13.22 thioanisole + NADPH + H+ + O2 - Acinetobacter calcoaceticus NCIMB 9871 ? - ? 398417 1.14.13.22 thioanisole + NADPH + H+ + O2 - Thermocrispum municipale (R)-methyl phenyl sulfoxide + NADP+ + H2O - ? 463058 1.14.13.22 trans-hex-2-enyl phenyl selenide + NADPH + O2 - Acinetobacter sp. ? - ? 288532 1.14.13.22 triethylphosphite + NADPH + O2 - Acinetobacter sp. ? - ? 288533 1.14.13.22 [(2-chloroethyl)sulfanyl]benzene + NADPH + H+ + O2 - Thermocrispum municipale (R)-2-chloroethyl phenyl sulfoxide + NADP+ + H2O - ? 463096 1.14.13.22 [(2-hydroxyethyl)sulfanyl]benzene + NADPH + H+ + O2 - Thermocrispum municipale (R)-2-hydroxyethyl phenyl sulfoxide + NADP+ + H2O - ? 463097