1.13.11.B6 (9E,11Z,15E)-octadeca-9,11,15-trienoic acid + O2 - Nakataea oryzae ? - ? 425137 1.13.11.B6 (9E,11Z,15E)-octadeca-9,11,15-trienoic acid + O2 - Nakataea oryzae CBS 288.54 ? - ? 425137 1.13.11.B6 (9Z,12Z)-octadeca-9,12-dienoic acid + O2 i.e. linoleic acid Lasiodiplodia theobromae (12Z)-9-hydroxy-10-oxo-12-octadecenoic acid the alpha-ketol is the main metabolite formed from (9R)-hydroperoxyoctadecadienoic acid ? 424406 1.13.11.B6 (9Z,12Z)-octadeca-9,12-dienoic acid + O2 i.e. linoleic acid Lasiodiplodia theobromae 2334 (12Z)-9-hydroxy-10-oxo-12-octadecenoic acid the alpha-ketol is the main metabolite formed from (9R)-hydroperoxyoctadecadienoic acid ? 424406 1.13.11.B6 (9Z,12Z)-octadeca-9,12-dienoic acid + O2 i.e. linoleic acid Lasiodiplodia theobromae CBS 117454 (12Z)-9-hydroxy-10-oxo-12-octadecenoic acid the alpha-ketol is the main metabolite formed from (9R)-hydroperoxyoctadecadienoic acid ? 424406 1.13.11.B6 (9Z,12Z)-octadeca-9,12-dienoic acid + O2 i.e. linoleic acid Lasiodiplodia theobromae CBS 122127 (12Z)-9-hydroxy-10-oxo-12-octadecenoic acid the alpha-ketol is the main metabolite formed from (9R)-hydroperoxyoctadecadienoic acid ? 424406 1.13.11.B6 (9Z,12Z)-octadeca-9,12-dienoic acid + O2 alpha-linoleate is converted via two intermediates, (9Z,11S,12Z)-11-hydroperoxy-9,12-octadecenoate and (9Z,11E,13R)-13-hydroperoxy-9,12-octadecadienoate, which are isomerized to the end product, probably after oxidation to peroxyl radicals, beta-fragmentation, and oxygen insertion at C-9 Nakataea oryzae (9S,10E,12Z)-9-hydroperoxy-octadeca-10,12-dienoate - ? 425142 1.13.11.B6 (9Z,12Z)-octadeca-9,12-dienoic acid + O2 alpha-linoleate is converted via two intermediates, (9Z,11S,12Z)-11-hydroperoxy-9,12-octadecenoate and (9Z,11E,13R)-13-hydroperoxy-9,12-octadecadienoate, which are isomerized to the end product, probably after oxidation to peroxyl radicals, beta-fragmentation, and oxygen insertion at C-9 Nakataea oryzae CBS 288.54 (9S,10E,12Z)-9-hydroperoxy-octadeca-10,12-dienoate - ? 425142 1.13.11.B6 (9Z,12Z,15Z)-octadeca-9,12,15-trienoic acid + O2 - Zea mays ? - ? 395110 1.13.11.B6 (9Z,12Z,15Z)-octadeca-9,12,15-trienoic acid + O2 gamma-linoleate is oxidized at C-9, C-11, and C-13 Nakataea oryzae ? - ? 395110 1.13.11.B6 (9Z,12Z,15Z)-octadeca-9,12,15-trienoic acid + O2 gamma-linoleate is oxidized at C-9, C-11, and C-13 Nakataea oryzae CBS 288.54 ? - ? 395110 1.13.11.B6 (9Z,12Z,15Z)-octadeca-9,12,15-trienoic acid + O2 i.e. alpha-linoleic acid Lasiodiplodia theobromae (9R,10E,12Z,15Z)-9-hydroperoxyoctadeca-10,12,15-trienoic acid + (9Z,12Z,15Z)-9-hydroxy-10-oxooctadeca-12,15-dienoic acid - ? 424407 1.13.11.B6 (9Z,12Z,15Z)-octadeca-9,12,15-trienoic acid + O2 i.e. alpha-linoleic acid Lasiodiplodia theobromae 2334 (9R,10E,12Z,15Z)-9-hydroperoxyoctadeca-10,12,15-trienoic acid + (9Z,12Z,15Z)-9-hydroxy-10-oxooctadeca-12,15-dienoic acid - ? 424407 1.13.11.B6 (9Z,12Z,15Z)-octadeca-9,12,15-trienoic acid + O2 i.e. alpha-linoleic acid Lasiodiplodia theobromae CBS 117454 (9R,10E,12Z,15Z)-9-hydroperoxyoctadeca-10,12,15-trienoic acid + (9Z,12Z,15Z)-9-hydroxy-10-oxooctadeca-12,15-dienoic acid - ? 424407 1.13.11.B6 (9Z,12Z,15Z)-octadeca-9,12,15-trienoic acid + O2 i.e. alpha-linoleic acid Lasiodiplodia theobromae CBS 122127 (9R,10E,12Z,15Z)-9-hydroperoxyoctadeca-10,12,15-trienoic acid + (9Z,12Z,15Z)-9-hydroxy-10-oxooctadeca-12,15-dienoic acid - ? 424407 1.13.11.B6 1,2-di-O-alpha-linolenoyl-3-O-beta-D-galactopyranosyl-sn-glycerol + O2 low activity with the wild-type enzyme, no activity with mutant A562G Zea mays ? - ? 425225 1.13.11.B6 2-linoleoyl-sn-glycero-3-phosphorylcholine + O2 low activity of wild-type and A562G mutant. The wild-type enzyme predominantly produces (13S)-hydroperoxide. The A562G mutant form possesses lesser regio- and stereospecificity during the dioxygenation of lysoPC. It produces 28% of (10E,12Z)-9-hydroperoxide and 30% of (9Z,11E)-13-hydroperoxide along with 41% of (all-E)-hydroperoxides. While 9-hydroperoxide is present mainly (61%) as S-enantiomer, (9Z,11E)-13-hydroperoxide is nearly racemic Zea mays ? - ? 425432 1.13.11.B6 2-linoleoyl-sn-glycero-3-phosphorylcholine + O2 the wild-type ZmLOX produces predominantly (13S)-hydroperoxide. In contrast, the A562G mutant produces excessively (9S)-hydroperoxide. The oxidation of 2-linoleoyl-sn-glycero-3-phosphorylcholine exhibits the limited regio- and stereospecificity. But the A562G mutant form possesses lesser regio- and stereospecificity Zea mays ? - ? 425432 1.13.11.B6 all-cis-9,12,15-octadecatrienoic acid + O2 i.e. alpha-linoleic acid Lasiodiplodia theobromae (9R)-hydroperoxy-(10E,12Z,15Z)-octadecatrienoic acid + 9-hydroxy-10-oxo-(12Z,15Z)-octadecadienoic acid - ? 424634 1.13.11.B6 all-cis-9,12,15-octadecatrienoic acid + O2 i.e. alpha-linoleic acid Lasiodiplodia theobromae 2334 (9R)-hydroperoxy-(10E,12Z,15Z)-octadecatrienoic acid + 9-hydroxy-10-oxo-(12Z,15Z)-octadecadienoic acid - ? 424634 1.13.11.B6 all-cis-9,12,15-octadecatrienoic acid + O2 i.e. alpha-linoleic acid Lasiodiplodia theobromae CBS 117454 (9R)-hydroperoxy-(10E,12Z,15Z)-octadecatrienoic acid + 9-hydroxy-10-oxo-(12Z,15Z)-octadecadienoic acid - ? 424634 1.13.11.B6 all-cis-9,12,15-octadecatrienoic acid + O2 i.e. alpha-linoleic acid Lasiodiplodia theobromae CBS 122127 (9R)-hydroperoxy-(10E,12Z,15Z)-octadecatrienoic acid + 9-hydroxy-10-oxo-(12Z,15Z)-octadecadienoic acid - ? 424634 1.13.11.B6 all-cis-9,12-octadecadienoic acid + O2 i.e. linoleic acid Lasiodiplodia theobromae 9-hydroxy-10-oxo-12Z-octadecenoic acid the alpha-ketol is the main metabolite formed from 9R-hydroperoxyoctadecadienoic acid ? 424635 1.13.11.B6 arachidonate + O2 specific activity is 13% of the activity with linoleate Pisum sativum ? products not determined ? 408405 1.13.11.B6 linoleate + O2 - Zea mays (9S,10E,12Z)-9-hydroperoxy-10,12-octadecadienoate - ? 407265 1.13.11.B6 linoleate + O2 - Oryza sativa (9S,10E,12Z)-9-hydroperoxy-10,12-octadecadienoate + (9Z,11E,13S)-13-hydroperoxy-9,11-octadecadienoate the ratio of (9Z,11E,13S)-13-hydroperoxy-9,11-octadecadienoate to (9S,10E,12Z)-9-hydroperoxy-10,12-octadecadienoate is 4:3 ? 407266 1.13.11.B6 linoleate + O2 - Corylus avellana (9S,10E,12Z)-9-hydroperoxy-10,12-octadecadienoate + (9Z,11E,13S)-13-hydroperoxy-9,11-octadecadienoate (9S,10E,12Z)-9-hydroperoxy-10,12-octadecadienoate is the main product (about 70% of the total hydroperoxides), predominantly S configuration ? 407266 1.13.11.B6 linoleate + O2 - Oryza sativa (9S,10E,12Z)-9-hydroperoxy-10,12-octadecadienoate + (9Z,11E,13S)-13-hydroperoxy-9,11-octadecadienoate dual positional specificity. The ratio of (10E,12Z)-9-hydroperoxy-10,12-octadecadienoate to (9Z,11E)-13-hydroperoxy-9,11-octadecadienoate is 4:3. Both products are predominantly in the S configuration ? 407266 1.13.11.B6 linoleate + O2 soybean lipoxygenase-1 produces a preponderance of two chiral products from linoleic acid, (9Z,11E,13S)-13-hydroperoxy-9,11-octadecadienoate and (9S,10E,12Z)-9-hydroperoxy-10,12-octadecadienoate. (9Z,11E,13S)-13-hydroperoxy-9,11-octadecadienoate is generated at all pH values, but in the presence of Tween 20, (9S,10E,12Z)-9-hydroperoxy-10,12-octadecadienoate does not form at pH values above 8.5. As the pH decreases below 8.5, the proportion of (9S,10E,12Z)-9-hydroperoxy-10,12-octadecadienoate increases linearly until at pH 6 it constitutes about 25% of the chiral products attributed to enzymic action. Below pH 6, lipoxygenase activity is barely measurable, and the hydroperoxide product arises mainly from autoxidation and possibly non-enzymic oxygenation of the pentadienyl radical formed by the enzyme. The change in percent enzymically formed 9-hydroperoxide between pH 6.0 and 8.5 parallels the pH plot of a sodium linoleate/linoleic acid titration. It is concluded that the (9S)-hydroperoxide is formed only from the nonionized carboxylic acid form of linoleic acid. Methyl esterification of linoleic acid blocks the formation of the (9S,10E,12Z)-9-hydroperoxy-10,12-octadecadienoate by lipoxygenase-1, but not the (13S)-hydroperoxide. Since the hydroperoxydiene moieties of the (9S)- and (13S)-hydroperoxides are spatially identical when the molecules are arranged head to tail in opposite orientations, it is suggested that the carboxylic acid form of the substrate can arrange itself at the active site in either orientation, but the carboxylate anion can be positioned only in one orientation. Active-site model for soybean lipoxygenase-1 Glycine max (9S,10E,12Z)-9-hydroperoxy-10,12-octadecadienoate + (9Z,11E,13S)-13-hydroperoxy-9,11-octadecadienoate - ? 407266 1.13.11.B6 linoleate + O2 - Solanum tuberosum (10E,12Z)-9-hydroperoxy-10,12-octadecadienoate + (9Z,11E)-13-hydroperoxy-9,11-octadecadienoate dual positional specificity: the enzyme produces roughly equimolar amounts of (10E,12Z)-9-hydroperoxy-10,12-octadecadienoate and (9Z,11E)-13-hydroperoxy-9,11-octadecadienoate. The R/S stereoconfiguration of the products is not determined ? 409756 1.13.11.B6 linoleate + O2 - Arachis hypogaea (10E,12Z)-9-hydroperoxy-10,12-octadecadienoate + (9Z,11E)-13-hydroperoxy-9,11-octadecadienoate the linoleic acid oxidation products are ca. 70% and (9Z,11E)-13-hydroperoxy-9,11-octadecadienoate and 30% (10E,12Z)-9-hydroperoxy-10,12-octadecadienoate both of which are mainly the S-stereoisomer ? 409756 1.13.11.B6 linoleate + O2 - Pisum sativum (10E,12Z)-9-hydroperoxy-10,12-octadecadienoate + (9Z,11E)-13-hydroperoxy-9,11-octadecadienoate the ratio of (9Z,11E)-13-hydroperoxy-11,13-octadecadienoate to (10E,12Z)-9-hydroperoxy-10,12-octadecadienoate is 1:2 for pea seed LOX-3 and recombinant LOX-3. The R/S stereoconfiguration of the products is not determined ? 409756 1.13.11.B6 linoleate + O2 - Pisum sativum (10E,12Z)-9-hydroperoxy-10,12-octadecadienoate + (9Z,11E)-13-hydroperoxy-9,11-octadecadienoate the ratio of (9Z,11E)-13-hydroperoxy-9,11-octadecadienoate to (10E,12Z)-9-hydroperoxy-10,12-octadecadienoate is 4:1 for LOX-2 from from pea seed and 7:1 for the recombinant enzyme LOX-2. The R/S stereoconfiguration of the product is not determined ? 409756 1.13.11.B6 linoleate + O2 - Pisum sativum (10E,12Z)-9-hydroperoxy-10,12-octadecadienoate + (9Z,11E)-13-hydroperoxy-9,11-octadecadienoate the ratio of 9-hydroperoxy-(10E,12Z)-octadecadienoate to 13-hydroperoxy-(10E,12Z)-octadecadienoate is 3:1 ? 409756 1.13.11.B6 linoleate + O2 according to their positional specificity of linoleic acid oxygenation plant LOX can be classified into linoleate 9-lipoxygenases and linoleate 13-lipoxygenases. A critical valine is detected at the active site of 9-LOX. In contrast, more bulky phenylalanine or histidine residues are found at this position in 13-LOX. Cloning of LOX-isoform from Momordica charantia and multiple amino acid alignments indicate the existence of a glutamine (Gln599) at the position where 13-LOX usually carry histidine or phenylalanine residues. Analyzing the pH-dependence of the positional specificity of linoleic acid oxygenation it is observed that at pH-values higher than 7.5 this enzyme constitutes a linoleate 13-lipoxygenase whereas at lower pH, (9S)-hydroperoxy-(10E,12Z)-octadecadienoate is the major reaction product. The structural basis for this variable reaction specificity is explored by site directed mutagenesis studies. Site-directed mutagenesis of Gln599 to His (Gln599His) converts the enzyme to a pure 13-lipoxygenase. The reaction specificity of certain LOX-isoforms is not an absolute enzyme property but may be impacted by reaction conditions such as pH of the reaction mixture Momordica charantia (10E,12Z)-9-hydroperoxy-10,12-octadecadienoate + (9Z,11E)-13-hydroperoxy-9,11-octadecadienoate variable positional specificity of linoleic acid oxygenation depending on the pH of the reaction mixture. Below pH 7.5, (10E,12Z)-9-hydroperoxy-10,12-octadecadienoate is the major reaction product whereas at higher pH (9Z,11E)-13-hydroperoxy-9,11-octadecadienoate is dominant. (9Z,11E)-13-hydroperoxy-9,11-octadecadienoate is preferentially formed as S enantiomer (85%) and the S/R-ratio does hardly vary over the entire pH-range. In contrast, the enantiomers composition of (10E,12Z)-9-hydroperoxy-10,12-octadecadienoate is pH-dependent. Below pH 7.5 a strong preponderance of the S enantiomer is observed. At higher pH-values the relative share of (9R,10E,12Z)-9-hydroperoxy-10,12-octadecadienoate becomes increasingly abundant reaching a 1:1 ratio at pH 9 ? 409756 1.13.11.B6 linoleate + O2 identification of some of the primary determinants at the catalytic centre of pea 9/13-LOX. Validation of a model of linoleate-binding to this enzyme. Evidence is provided that the primary determinants of pocket volume and conformation are more important than substrate orientation in pea lipoxygenase catalysis. Inverse models may account for the positional specificity of only selected plant lipoxygenases Pisum sativum (10E,12Z)-9-hydroperoxy-10,12-octadecadienoate + (9Z,11E)-13-hydroperoxy-9,11-octadecadienoate ratio of (9Z,11E)-13-hydroperoxy-9,11-octadecadienoate to (10E,12Z)-9-hydroperoxy-10,12-octadecadienoate: 1.1 (wild-type enzyme), 1.6 (mutant enzyme T579S), 1.5 (mutant enzyme V570I), 1.4 (mutant enzyme T579F), 1.3 (mutant enzyme F580A), 0.9 (mutant enzyme L569V), 1.7 (mutant enzyme W523A), 1.3 (mutant enzyme F580V) ? 409756 1.13.11.B6 linoleate + O2 the dual positional specific maize lipoxygenase is not able to catalyze the oxidation of trilinolein or trilinolenin even in the presence of detergent. The enzyme seems to ultilize only free fatty acid as a substrate. The solubilization of substrate involves the incorporation of substrate molecules into the detergent micelles, which leads to decreased availability of effective free fatty acids for binding with the LOX enzyme. The unique initial burst phenomenon of the maize LOX observed in the oxidation of linoleate at low pH may also be attributed to the availability of free fatty acids as substrates Zea mays (10E,12Z)-9-hydroperoxy-10,12-octadecadienoate + (9Z,11E)-13-hydroperoxy-9,11-octadecadienoate - ? 409756 1.13.11.B6 linoleate + O2 - Malus domestica (9R,10E,12Z)-9-hydroperoxy-10,12-octadecadienoate + (9Z,11E,13R)-13-hydroperoxy-9,11-octadecadienoate - ? 409759 1.13.11.B6 linoleate + O2 - Glycine max (9R,10E,12Z)-9-hydroperoxy-10,12-octadecadienoate + (9Z,11E,13R)-13-hydroperoxy-9,11-octadecadienoate the enzyme delivers a 50:50 mixture of (9R,10E,12Z)-9-hydroperoxy-10,12-octadecadienoate + (9Z,11E,13R)-13-hydroperoxy-9,11-octadecadienoate, with higher turn out of R stereoisomers over S isomers (60:40) ? 409759 1.13.11.B6 linoleate + O2 the catalytic efficiency of the recombinant olive LOX was significantly higher for linoleic acid hydroperoxidation than for linolenic acid hydroperoxidation Olea europaea (9S,10E,12Z)-9-hydroperoxy-10,12-octadecadienoate + (9Z,11E,13R)-13-hydroperoxy-9,11-octadecadienoate dual positional specificity: the enzyme forms (9S,10E,12Z)-9-hydroperoxy-10,12-octadecadienoate and (9Z,11E,13R)-13-hydroperoxy-9,11-octadecadienoate in a 2:1 ratio, the products are predominantly in 9S and 13R configuration ? 409760 1.13.11.B6 linoleate + O2 - Zea mays (9Z,11E,13S)-13-hydroperoxyoctadeca-9,11-dienoate - ? 424888 1.13.11.B6 linoleate + O2 - Zea mays (9S,10E,12Z)-9-hydroperoxyoctadeca-10,12-dienoate - ? 426621 1.13.11.B6 linoleate + O2 - Malus domestica 9-hydroperoxy-10,12-octadecadienoate + 13-hydroperoxy-9,11-octadecadienoate - ? 440314 1.13.11.B6 linolenate + O2 - Zea mays (10E,12Z)-9-hydroperoxy-10,12-octadecadienoate + (9Z,11E)-13-hydroperoxy-9,11-octadecadienoate the enzyme forms (9Z,11E)-13-hydroperoxy-9,11-octadecadienoate and (10E,12Z)-9-hydroperoxy-10,12-octadecadienoate in a 6:4 ratio. The R/S stereoconfiguration of the products is not determined ? 409774 1.13.11.B6 linolenate + O2 - Malus domestica ? - ? 409775 1.13.11.B6 linolenate + O2 specific activity is 17% of the activity with linoleate. The R/S stereoconfiguration of the product is not determined Pisum sativum ? products not determined ? 409775 1.13.11.B6 linolenate + O2 the catalytic efficiency of the recombinant olive LOX is significantly higher for linoleic acid hydroperoxidation than for linolenic acid hydroperoxidation Olea europaea ? - ? 409775 1.13.11.B6 monolinolenoylglycerol + O2 isolated from flax leaves, both the wild-type ZmLOX and A562G mutant dioxygenate monolinolenoylglycerol. Both oxidize the monolinolenoylglycerol predominantly into (9S)-hydroperoxide. The A562G mutation does not affect the relative yield of 13-hydroperoxide, but increases the proportion of (13R)-enantiomer Zea mays ? - ? 426692 1.13.11.B6 monolinolenoylglycerol + O2 wild-type enzyme and mutant A562G predominantly produce (9S)-hydroperoxide Zea mays ? - ? 426692 1.13.11.B6 additional information the enzyme catalyzes oxidation of arachidonate with lower activity Solanum tuberosum ? - ? 89 1.13.11.B6 additional information both the wild type ZmLOX and A562G mutant dioxygenate monolinolenoylglycerol and 2-linoleoyl-sn-glycero-3-phosphorylcholine, the latter being a poor substrate. Both oxidize the monolinolenoylglycerol predominantly into (9S)-hydroperoxide. The oxidation of 2-linoleoyl-sn-glycero-3-phosphorylcholine exhibits limited regio- and stereospecificity: the wild-type ZmLOX produces some predominance of (13S)-hydroperoxide. In contrast, the A562G mutant produces some excess of (9S)-hydroperoxide Zea mays ? - ? 89 1.13.11.B6 additional information Bulky polar heads of glycerolipids cannot penetrate into the LOX active site. Both (9S)- and (13S)-hydroperoxides can be produced when the substrate is arranged within LOX active site in the methyl end first orientation. 1-Linoleoyl-snglycero-3-phosphorylcholine is a poor substrate for both wild-type and A562G mutant. No activity of wild-type and mutant with 2-O-alpha-linolenoyl-3-O-beta-D-galactopyranosyl-sn-glycerol, dilinolenoylglycerol, and trilinolenoylglycerol Zea mays ? - ? 89 1.13.11.B6 additional information cf. EC 1.13.11.45, LC- and GC-MS analysis product analysis, overview. Authentic (11S)-hydroperoxyoctadecadienoate is rapidly transformed to 9-hydroperoxyoctadecadienoate by 9S-MnLOX, and only traces of 13-hydroperoxyoctadecadienoate. 9S-MnLOX also partly transforms authentic (13R)-hydroperoxyoctadecadienoate to (9S)-hydroperoxyoctadecadienoate Nakataea oryzae ? - ? 89 1.13.11.B6 additional information the putative 9R-dioxygenase catalyzes stereospecific removal of the 11R hydrogen followed by suprafacial attack of dioxygen at C-9 Lasiodiplodia theobromae ? - ? 89 1.13.11.B6 additional information regio- and stereospecificity analysis of isozyme substrate specificity, recombinant LOX1:Md:1a, LOX1:Md:1c, LOX2:Md:2a and LOX2:Md:2b isozymes show 13/9-LOX, 9-LOX, 13/9-LOX and 13-LOX activity with linoleic acid, respectively. While products of LOX1:Md:1c and LOX2:Md:2b are S-configured, LOX1:Md:1a and LOX2:Md:2a form 13(R)-hydroperoxides as major products. Oxygenation in the carbon backbone of linoleic acid occurs either at carbon atom 9 (9-LOX) or 13 (13-LOX), forming the corresponding hydroperoxy derivatives, respectively. LOX enzymes are not perfectly specific and biocatalysts that produce more than 10% of the alternative regio-isomer are called dual positional specific LOX Malus domestica ? - ? 89 1.13.11.B6 additional information the putative 9R-dioxygenase catalyzes stereospecific removal of the 11R hydrogen followed by suprafacial attack of dioxygen at C-9 Lasiodiplodia theobromae 2334 ? - ? 89 1.13.11.B6 additional information cf. EC 1.13.11.45, LC- and GC-MS analysis product analysis, overview. Authentic (11S)-hydroperoxyoctadecadienoate is rapidly transformed to 9-hydroperoxyoctadecadienoate by 9S-MnLOX, and only traces of 13-hydroperoxyoctadecadienoate. 9S-MnLOX also partly transforms authentic (13R)-hydroperoxyoctadecadienoate to (9S)-hydroperoxyoctadecadienoate Nakataea oryzae CBS 288.54 ? - ? 89 1.13.11.B6 additional information the putative 9R-dioxygenase catalyzes stereospecific removal of the 11R hydrogen followed by suprafacial attack of dioxygen at C-9 Lasiodiplodia theobromae CBS 117454 ? - ? 89 1.13.11.B6 additional information the putative 9R-dioxygenase catalyzes stereospecific removal of the 11R hydrogen followed by suprafacial attack of dioxygen at C-9 Lasiodiplodia theobromae CBS 122127 ? - ? 89 1.13.11.B6 phosphorylcholine + O2 activity with the wild-type enzyme, no activity with mutant A562G Zea mays ? - ? 426934