1.14.15.8 4-androstene-3,17-dione + reduced ferredoxin + O2 Kd value of androstenedione is 0.387 mM Bacillus sp. PAMC 23377 15beta-hydroxyandrost-4-en-3,17-dione + oxidized ferredoxin + H2O - ? 442888 1.14.15.8 nandrolone + reduced ferredoxin + O2 - Bacillus sp. PAMC 23377 ? + oxidized ferredoxin + H2O - ? 443788 1.14.15.8 11-deoxycorticosterone + reduced adrenodoxin + O2 - Priestia megaterium 15beta-hydroxy-11-deoxycorticosterone + oxidized adrenodoxin + H2O - ? 404979 1.14.15.8 11-deoxycorticosterone + reduced adrenodoxin + O2 adrenodoxin is a [2Fe-2S] ferredoxin involved in electron transfer from NADPH+ (via a reductase) to cytochrome P-450 in the adrenal gland, 15beta-hydroxy-deoxycorticosterone is the only product that is observed, both in the case of wild-type CYP106A2 and all the mutants (except T396R) Priestia megaterium 15beta-hydroxy-11-deoxycorticosterone + oxidized adrenodoxin + H2O - ? 404979 1.14.15.8 11-deoxycorticosterone + reduced adrenodoxin + O2 deoxycorticosterone binds in the heme pocket near the iron ligand Priestia megaterium 15beta-hydroxy-11-deoxycorticosterone + oxidized adrenodoxin + H2O - ? 404979 1.14.15.8 11-deoxycorticosterone + reduced adrenodoxin + O2 - Priestia megaterium 15beta-hydroxy-11-deoxycorticosterone + 7beta,15beta-dihydroxy-11-deoxycorticosterone + oxidized adrenodoxin + H2O - ? 442714 1.14.15.8 11-deoxycorticosterone + reduced ferredoxin + O2 ferredoxin from the cyanobacterium Anabaena PCC 7119 Priestia megaterium 15beta-hydroxy-11-deoxycorticosterone + oxidized ferredoxin + H2O - ? 404981 1.14.15.8 11-deoxycorticosterone + reduced flavodoxin + O2 flavodoxin from the cyanobacterium Anabaena PCC 7119 Priestia megaterium 15beta-hydroxy-11-deoxycorticosterone + oxidized flavodoxin + H2O - ? 404982 1.14.15.8 11-deoxycorticosterone + reduced megaredoxin + O2 megaredoxin is an iron-sulfur protein of Bacillus megaterium, megaredoxin has an apparent sulfur to iron ratio of 0.98 Priestia megaterium 15beta-hydroxy-11-deoxycorticosterone + oxidized megaredoxin + H2O - ? 404983 1.14.15.8 11-deoxycortisol + reduced adrenodoxin + O2 adrenodoxin is a [2Fe-2S] ferredoxin involved in electron transfer from NADPH+ (via a reductase) to cytochrome P-450 in the adrenal gland Priestia megaterium 15beta-15,17,21-trihydroxypregn-4-ene-3,20-dione + oxidized adrenodoxin + H2O - ? 403302 1.14.15.8 11-deoxycortisol + reduced adrenodoxin + O2 - Priestia megaterium 15beta-hydroxy-11-deoxycortisol + oxidized adrenodoxin + H2O - ? 442715 1.14.15.8 11-oxo-beta-boswellic acid + reduced ferredoxin + O2 a pentacyclic triterpene, 15beta-hydroxylation Priestia megaterium (3alpha,15beta)-3,15-dihydroxy-11-oxours-12-en-24-oic acid + H2O - ? 425304 1.14.15.8 11beta-hydroxy-4-androstene-3,17-dione + reduced adrenodoxin + O2 - Priestia megaterium ? + oxidized adrenodoxin + H2O - ? 442721 1.14.15.8 17alpha-hydroxyprogesterone + reduced megaredoxin + O2 megaredoxin is an iron-sulfur protein of Bacillus megaterium, megaredoxin has an apparent sulfur to iron ratio of 0.98 Priestia megaterium (15beta,17alpha)-15,17-dihydroxyprogesterone + oxidized megaredoxin + H2O - ? 403314 1.14.15.8 17alpha-methyltestosterone + reduced adrenodoxin + O2 - Priestia megaterium ? + oxidized adrenodoxin + H2O - ? 442730 1.14.15.8 19-nortestosterone + reduced adrenodoxin + O2 - Priestia megaterium ? + oxidized adrenodoxin + H2O - ? 442731 1.14.15.8 20alpha-dihydroprogesterone + reduced megaredoxin + O2 megaredoxin is an iron-sulfur protein of Bacillus megaterium, megaredoxin has an apparent sulfur to iron ratio of 0.98 Priestia megaterium (15beta,20alpha)-15-hydroxy-20-dihydroprogesterone + oxidized megaredoxin + H2O - ? 403647 1.14.15.8 4-androstene-3,17-dione + reduced adrenodoxin + O2 - Priestia megaterium 15beta-hydroxyandrostene-3,17-dione + oxidized adrenodoxin + H2O - ? 442887 1.14.15.8 4-androstene-3,17-dione + reduced megaredoxin + O2 megaredoxin is an iron-sulfur protein of Bacillus megaterium, megaredoxin has an apparent sulfur to iron ratio of 0.98 Priestia megaterium 15beta-hydroxyandrostene-3,17-dione + oxidized megaredoxin + H2O - ? 403807 1.14.15.8 6alpha-fluoro-16alpha-methyl-deoxycorticosterone + reduced ferredoxin + O2 - Priestia megaterium 15beta-hydroxy-6alpha-fluoro-16alpha-methyl-deoxycorticosterone + oxidized ferredoxin + H2O - ? 404087 1.14.15.8 abietic acid + reduced adrenodoxin + O2 - Priestia megaterium 12-hydroxyabietic acid + oxidized adrenodoxin + H2O - ? 425864 1.14.15.8 abietic acid + reduced adrenodoxin + O2 binding of abietic acid results in a type II difference spectrum typical for nitrogenous inhibitors Priestia megaterium ? + oxidized adrenodoxin + H2O - ? 443006 1.14.15.8 abietic acid + reduced ferredoxin + O2 a pentacyclic triterpene Priestia megaterium ? - ? 425865 1.14.15.8 corticosterone + reduced adrenodoxin + O2 - Priestia megaterium 15beta-hydroxycorticosterone + oxidized adrenodoxin + H2O - ? 443402 1.14.15.8 corticosterone + reduced megaredoxin + O2 megaredoxin is an iron-sulfur protein of Bacillus megaterium, preferred substrate, megaredoxin has an apparent sulfur to iron ratio of 0.98 Priestia megaterium 15beta-hydroxycorticosterone + oxidized megaredoxin + H2O - ? 404705 1.14.15.8 cortisone + reduced adrenodoxin + O2 - Priestia megaterium 15beta-hydroxycortisone + oxidized adrenodoxin + H2O - ? 443403 1.14.15.8 dehydroabietic acid + reduced adrenodoxin + O2 - Priestia megaterium ? + oxidized adrenodoxin + H2O - ? 443449 1.14.15.8 dehydroepiandrosterone + reduced adrenodoxin + O2 - Priestia megaterium 7beta-hydroxy-dehydroepiandrosterone + oxidized adrenodoxin + H2O - ? 443452 1.14.15.8 deoxycorticosterone + reduced ferredoxin + O2 - Priestia megaterium 15beta-hydroxy-11-deoxycorticosterone + oxidized ferredoxin + H2O - r 451331 1.14.15.8 deoxycorticosterone + reduced flavodoxin + O2 - Priestia megaterium 15beta-hydroxy-11-deoxycorticosterone + oxidized flavodoxin + H2O - r 451332 1.14.15.8 dexamethasone + reduced adrenodoxin + O2 - Priestia megaterium ? + oxidized adrenodoxin + H2O - ? 443468 1.14.15.8 digitoxigenin + reduced adrenodoxin + O2 - Priestia megaterium ? + oxidized adrenodoxin + H2O - ? 443480 1.14.15.8 imipramine + reduced adrenodoxin + O2 - Priestia megaterium desipramine + oxidized adrenodoxin + H2O - ? 426506 1.14.15.8 isopimaric acid + reduced adrenodoxin + O2 - Priestia megaterium ? + oxidized adrenodoxin + H2O - ? 443661 1.14.15.8 additional information hydroxylates a variety of 3-oxo-DELTA4-steroids in position 15beta in the presence of NADPH and O2. Ring A-reduced, aromatic, and 3beta-hydroxy-DELTA4-steroids do not serve as substrates Priestia megaterium ? - ? 89 1.14.15.8 additional information the specificity of hydroxylation in beta-position can be altered by the choice of the electron transfer system. Replacing the natural electron transfer partners by peroxides, the ratio of 15alpha-/15beta-hydroxylation of progesterone is increased 1.3fold Priestia megaterium ? - ? 89 1.14.15.8 additional information CYP106A2 catalyzes hydroxylations of a variety of 3-oxo-D4-steroids such as progesterone and deoxycorticosterone, mainly in the 15beta-position. The diterpene resin acid abietic acid is a substrate, that is converted to 12alpha- and 12beta-hydroxyabietic acid, catalytic site binding structure, homology modelling, overview Priestia megaterium ? - ? 89 1.14.15.8 additional information high-throughput substrate screening and binding affinities, substrate docking, overview Priestia megaterium ? - ? 89 1.14.15.8 additional information CYP106A2 from hydroxylates a variety of 3-oxo-DELTA4 steroids and catalyzes a one-step regioselective allylic hydroxylation of the diterpene abietic acid Priestia megaterium ? - ? 89 1.14.15.8 additional information enzyme reaction is coupled to NADPH oxidation, overview Priestia megaterium ? - ? 89 1.14.15.8 additional information enzyme produces hydroxylated metabolites at positions 6beta, 7beta, 9alpha, and 15beta and shows additionally 11-oxidase activity. No substrates: beta-estradiol, estrone, adrenosterone, and 19-hydroxyandrostenedione Priestia megaterium ? - ? 89 1.14.15.8 additional information enzyme produces hydroxylated metabolites at positions 6beta, 7beta, 9alpha,and 15beta and shows additionally 11-oxidase activity. No substrates: beta-estradiol, estrone, adrenosterone, and 19-hydroxyandrostenedione Priestia megaterium ? - ? 89 1.14.15.8 additional information the 3-oxo-DELTA4 moiety is not crucial for steroid conversion with CYP106A2. No substrates: estrone, estradiol, stigmasterol, and cholesterol Priestia megaterium ? - ? 89 1.14.15.8 prednisolone + reduced adrenodoxin + O2 - Priestia megaterium ? + oxidized adrenodoxin + H2O - ? 443856 1.14.15.8 prednisone + reduced adrenodoxin + O2 - Priestia megaterium ? + oxidized adrenodoxin + H2O - ? 443857 1.14.15.8 pregnenolone + reduced adrenodoxin + O2 - Priestia megaterium 7beta-hydroxy-pregnenolone + oxidized adrenodoxin + H2O - ? 443859 1.14.15.8 progesterone + reduced adrenodoxin + O2 adrenodoxin is a [2Fe-2S] ferredoxin involved in electron transfer from NADPH+ (via a reductase) to cytochrome P-450 in the adrenal gland, 15beta-hydroxy-progesterone is the main product of wild-type enzyme and all mutants. In order to gain insights into the structure and function of CYP106A2, whose crystal structure is unknown, a homology model has been created. The substrate progesterone is then docked into the active site to predict which residues might affect substrate binding. The model is substantiated by using a combination of theoretical and experimental investigations Priestia megaterium 15beta-hydroxy-progesterone + oxidized adrenodoxin + H2O - ? 406466 1.14.15.8 progesterone + reduced adrenodoxin + O2 adrenodoxin is a [2Fe-2S] ferredoxin involved in electron transfer from NADPH+ (via a reductase) to cytochrome P-450 in the adrenal gland Priestia megaterium 15beta-hydroxyprogesterone + oxidized adrenodoxin + H2O - ? 406467 1.14.15.8 progesterone + reduced adrenodoxin + O2 identification of monohydroxy progesterones using comparative HPLC and electrospray ionisation collision-induced dissociation mass spectrometry. 15beta-Hydroxy-progesterone is the main product. 6beta-Hydroxyprogesterone, 11alpha-hydroxyprogesterone, and 9alpha-hydroxyprogesterone are formed at small amounts Priestia megaterium 15beta-hydroxyprogesterone + oxidized adrenodoxin + H2O - ? 406467 1.14.15.8 progesterone + reduced adrenodoxin + O2 - Priestia megaterium 15beta-hydroxy-progesterone + 11alpha-hydroxy-progesterone + oxidized adrenodoxin + H2O - ? 443861 1.14.15.8 progesterone + reduced ferredoxin + O2 Bacillus megaterium ferredoxin may be replaced by adrenal ferredoxin Priestia megaterium 15beta-hydroxy-progesterone + oxidized ferredoxin + H2O - ? 406468 1.14.15.8 progesterone + reduced megaredoxin + O2 - Priestia megaterium 15beta-hydroxyprogesterone + oxidized megaredoxin + H2O - ? 406469 1.14.15.8 progesterone + reduced megaredoxin + O2 megaredoxin is an iron-sulfur protein of Bacillus megaterium, megaredoxin has an apparent sulfur to iron ratio of 0.98 Priestia megaterium 15beta-hydroxyprogesterone + oxidized megaredoxin + H2O - ? 406469 1.14.15.8 testosterone + reduced acceptor + O2 the major product is identified as 15beta-hydroxytestosterone. 6beta-Hydroxytestosterone and androst-4-ene-3,17-dione are present as minor products Priestia megaterium 15beta-hydroxytestosterone + oxidized acceptor + H2O - ? 406747 1.14.15.8 testosterone + reduced adrenodoxin + O2 - Priestia megaterium 15beta-hydroxytestosterone + oxidized adrenodoxin + H2O - ? 406748 1.14.15.8 testosterone + reduced megaredoxin + O2 megaredoxin is an iron-sulfur protein of Bacillus megaterium, megaredoxin has an apparent sulfur to iron ratio of 0.98 Priestia megaterium 15beta-hydroxytestosterone + oxidized megaredoxin + H2O - ? 406749 1.14.15.8 11-oxo-beta-boswellic acid + reduced ferredoxin + O2 a pentacyclic triterpene, 15beta-hydroxylation Priestia megaterium ATCC 13368 (3alpha,15beta)-3,15-dihydroxy-11-oxours-12-en-24-oic acid + H2O - ? 425304 1.14.15.8 abietic acid + reduced ferredoxin + O2 a pentacyclic triterpene Priestia megaterium ATCC 13368 ? - ? 425865 1.14.15.8 additional information CYP106A2 from hydroxylates a variety of 3-oxo-DELTA4 steroids and catalyzes a one-step regioselective allylic hydroxylation of the diterpene abietic acid Priestia megaterium ATCC 13368 ? - ? 89 1.14.15.8 additional information CYP106A2 catalyzes hydroxylations of a variety of 3-oxo-D4-steroids such as progesterone and deoxycorticosterone, mainly in the 15beta-position. The diterpene resin acid abietic acid is a substrate, that is converted to 12alpha- and 12beta-hydroxyabietic acid, catalytic site binding structure, homology modelling, overview Priestia megaterium ATCC 13368 ? - ? 89 1.14.15.8 additional information high-throughput substrate screening and binding affinities, substrate docking, overview Priestia megaterium ATCC 13368 ? - ? 89