5.3.2.6 (1Z)-1-(nitromethylidene)-3a,4,5,6,7,7a-hexahydro-1H-indene + acetaldehyde - Escherichia coli [1-(nitromethyl)-1H-inden-1-yl]acetaldehyde - ? 427745 5.3.2.6 (1Z)-4-methyl-1-nitropent-1-ene + acetaldehyde - Escherichia coli 5-methyl-3-(nitromethyl)hexanal - ? 427746 5.3.2.6 (2E)-2-hydroxy-3-phenylprop-2-enoate - Pseudomonas putida 2-oxo-3-phenylpropanoate - ? 427747 5.3.2.6 (2Z,4E)-2-hydroxyhexa-2,4-dienedioate - Archaeoglobus fulgidus (2E)-5-oxohex-2-enedioate - ? 419897 5.3.2.6 (2Z,4E)-2-hydroxyhexa-2,4-dienedioate 1,3- and 1,5-keto-enol tautomerization reactions are observed for 2-hydroxy-2,4-hexadienedioate. YwhB converts it to the 3S isomer of 2-oxo-4-hexenedioate in a highly stereoselective manner Bacillus subtilis (2E)-5-oxohex-2-enedioate main product ? 419897 5.3.2.6 (2Z,4E)-2-hydroxyhexa-2,4-dienedioate - Helicobacter pylori (2E)-5-oxohex-2-enedioic acid - ? 422179 5.3.2.6 (2Z,4E)-2-hydroxyhexa-2,4-dienedioate - Bacillus subtilis (3E)-2-oxohex-3-enedioate - ? 422180 5.3.2.6 (2Z,4E)-2-hydroxyhexa-2,4-dienedioate - Escherichia coli (3E)-2-oxohex-3-enedioate - ? 422180 5.3.2.6 (2Z,4E)-2-hydroxyhexa-2,4-dienedioate - Pseudomonas putida (3E)-2-oxohex-3-enedioate - ? 422180 5.3.2.6 (2Z,4E)-2-hydroxyhexa-2,4-dienedioate - Pseudomonas putida (3E)-2-oxohex-3-enedioate - r 422180 5.3.2.6 (2Z,4E)-2-hydroxyhexa-2,4-dienedioate - Helicobacter pylori (3E)-2-oxohex-3-enedioate - ? 422180 5.3.2.6 (2Z,4E)-2-hydroxyhexa-2,4-dienedioate - Archaeoglobus fulgidus (3E)-2-oxohex-3-enedioate - ? 422180 5.3.2.6 (2Z,4E)-2-hydroxyhexa-2,4-dienedioate - Methylibium petroleiphilum (3E)-2-oxohex-3-enedioate - ? 422180 5.3.2.6 (2Z,4E)-2-hydroxyhexa-2,4-dienedioate - Leptothrix cholodnii (3E)-2-oxohex-3-enedioate - r 422180 5.3.2.6 (2Z,4E)-2-hydroxyhexa-2,4-dienedioate - Staphylococcus aureus (3E)-2-oxohex-3-enedioate - r 422180 5.3.2.6 (2Z,4E)-2-hydroxyhexa-2,4-dienedioate - Staphylococcus aureus MRSA252 (3E)-2-oxohex-3-enedioate - r 422180 5.3.2.6 (2Z,4E)-2-hydroxyhexa-2,4-dienedioate - Leptothrix cholodnii SP-6 (3E)-2-oxohex-3-enedioate - r 422180 5.3.2.6 (3E)-6-oxohept-3-enedioate - Pseudomonas putida 2-hydroxy-2,4-heptadiene-1,7-dioate - ? 427761 5.3.2.6 (E)-1-nitro-2-(2-thienyl)ethene + isobutanal - Pseudomonas putida 2,2-dimethyl-4-nitro-3-(thiophen-2-yl)butanal - ? 444530 5.3.2.6 (E)-2-(furan-2-yl)nitroethene + isobutanal - Pseudomonas putida 3-(furan-2-yl)-2,2-dimethyl-4-nitrobutanal - ? 444531 5.3.2.6 (E)-2-(thiophen-2-yl)nitroethene + isobutanal - Pseudomonas putida 2,2-dimethyl-4-nitro-3-(thiophen-2-yl)butanal - ? 444532 5.3.2.6 1-chloro-4-[(Z)-2-nitroethenyl]benzene + acetaldehyde - Escherichia coli 3-(4-chlorophenyl)-4-nitrobutanal - ? 427830 5.3.2.6 1-fluoro-4-[(Z)-2-nitroethenyl]benzene + acetaldehyde - Escherichia coli 3-(4-fluorophenyl)-4-nitrobutanal - ? 427831 5.3.2.6 2-(cyclopentyloxy)-1-methoxy-4-[(Z)-2-nitroethenyl]benzene + acetaldehyde - Escherichia coli 3-[3-(cyclopentyloxy)-4-methoxyphenyl]-4-nitrobutanal - ? 427893 5.3.2.6 2-chloro-beta-nitrostyrene + acetaldehyde - Pseudomonas putida 3-(2-chlorophenyl)-4-nitrobutanal 51% yield ? 427900 5.3.2.6 2-hydroxy-2,4-heptadiene-1,7-dioate - Pseudomonas putida (3E)-2-oxohept-3-enedioate - ? 427910 5.3.2.6 2-hydroxy-2,4-hexadienedioate - Pseudomonas putida 2-oxo-3-hexenedioate - ? 419257 5.3.2.6 2-hydroxy-2,4-hexadienedioate i.e. 2-hydroxymuconate Chloroflexus aurantiacus 2-oxo-3-hexenedioate - r 419257 5.3.2.6 2-hydroxy-2,4-hexadienedioate i.e. 2-hydroxymuconate, the enzyme catalyzes the conversion of 2-hydroxy-2,4-hexadienedioate (or 2-hydroxymuconate) to 2-oxo-3-hexenedioate, where Pro-1 functions as a general base and shuttles a proton from the 2-hydroxyl group of the substrate to the C-5 position of the product. hh4-OT requires the amino-terminal proline and two arginines for the conversion of 2-hydroxymuconate to the product Chloroflexus aurantiacus 2-oxo-3-hexenedioate - r 419257 5.3.2.6 2-hydroxy-2,4-hexadienedioate i.e. 2-hydroxymuconate Chloroflexus aurantiacus J-10-fl 2-oxo-3-hexenedioate - r 419257 5.3.2.6 2-hydroxy-2,4-hexadienedioate i.e. 2-hydroxymuconate, the enzyme catalyzes the conversion of 2-hydroxy-2,4-hexadienedioate (or 2-hydroxymuconate) to 2-oxo-3-hexenedioate, where Pro-1 functions as a general base and shuttles a proton from the 2-hydroxyl group of the substrate to the C-5 position of the product. hh4-OT requires the amino-terminal proline and two arginines for the conversion of 2-hydroxymuconate to the product Chloroflexus aurantiacus J-10-fl 2-oxo-3-hexenedioate - r 419257 5.3.2.6 2-hydroxy-2,4-hexadienedioate - Pseudomonas putida mt-2 / ATCC 33015 / DSM 3931 / NCIB 12182 / NCIMB 12182 2-oxo-3-hexenedioate - ? 419257 5.3.2.6 2-hydroxy-2,4-hexadienedioate 4-OT with 2-hydroxy-2,4-hexadienedioate in D2O results in a racemic mixture of 2-oxo-[3-2H]-4-hexenedioate, suggesting that 4-OT may not catalyze a 1,3-keto-enol tautomerization reaction using this dienol Pseudomonas putida 2-oxo-3,4-hexenedioate - ? 419895 5.3.2.6 2-hydroxy-2,4-hexadienedioate 4-OT with 2-hydroxy-2,4-hexadienedioate in D2O results in a racemic mixture of 2-oxo-[3-2H]-4-hexenedioate, suggesting that 4-OT may not catalyze a 1,3-keto-enol tautomerization reaction using this dienol Pseudomonas putida mt-2 / ATCC 33015 / DSM 3931 / NCIB 12182 / NCIMB 12182 2-oxo-3,4-hexenedioate - ? 419895 5.3.2.6 2-hydroxy-2,4-pentadienoate - Bacillus subtilis 2-oxopent-3-enoic acid - ? 419258 5.3.2.6 2-hydroxy-2,4-pentadienoate - Helicobacter pylori 2-oxo-4-pentenoate - ? 422404 5.3.2.6 2-hydroxy-2,4-pentadienoate - Archaeoglobus fulgidus 2-oxo-4-pentenoate - ? 422404 5.3.2.6 2-hydroxy-2,4-pentadienoate - Pseudomonas putida (3E)-2-oxopent-3-enoate - ? 427911 5.3.2.6 2-hydroxy-4-trans-hexenedioate - Pseudomonas putida ? - ? 419901 5.3.2.6 2-hydroxy-4-trans-hexenedioate - Pseudomonas putida mt-2 / ATCC 33015 / DSM 3931 / NCIB 12182 / NCIMB 12182 ? - ? 419901 5.3.2.6 2-hydroxymuconate - Pseudomonas putida 2-oxo-3-hexenedioate - r 419260 5.3.2.6 2-hydroxymuconate - Methylibium petroleiphilum 2-oxo-3-hexenedioate - ? 419260 5.3.2.6 2-hydroxymuconate ketonization Pseudomonas putida 2-oxo-3-hexenedioate - ? 419260 5.3.2.6 2-hydroxymuconate ketonization Pseudomonas putida 2-oxo-3-hexenedioate - r 419260 5.3.2.6 2-hydroxymuconate the conjugated enol, 2-hydroxymuconate is an unusually stable dienol that is reportedly generated in the course of bacterial catabolism of catechol by the enzymes of the meta-fission pathway Pseudomonas putida 2-oxo-3-hexenedioate the dienol ketonizes chemically in aqueous solution and enzymatically by the action of 4-oxalocrotonate tautomerase to either the beta,gamma-unsaturated ketone or its alpha,beta-conjugated isomer 2-oxo-3-trans-hexenedioate r 419260 5.3.2.6 2-hydroxymuconate ketonization Pseudomonas putida mt-2 / ATCC 33015 / DSM 3931 / NCIB 12182 / NCIMB 12182 2-oxo-3-hexenedioate - ? 419260 5.3.2.6 2-hydroxymuconate ketonization Pseudomonas putida mt-2 / ATCC 33015 / DSM 3931 / NCIB 12182 / NCIMB 12182 2-oxo-3-hexenedioate - r 419260 5.3.2.6 2-hydroxymuconate the conjugated enol, 2-hydroxymuconate is an unusually stable dienol that is reportedly generated in the course of bacterial catabolism of catechol by the enzymes of the meta-fission pathway Pseudomonas putida mt-2 / ATCC 33015 / DSM 3931 / NCIB 12182 / NCIMB 12182 2-oxo-3-hexenedioate the dienol ketonizes chemically in aqueous solution and enzymatically by the action of 4-oxalocrotonate tautomerase to either the beta,gamma-unsaturated ketone or its alpha,beta-conjugated isomer 2-oxo-3-trans-hexenedioate r 419260 5.3.2.6 2-hydroxymuconate - Paenibacillus sp. 4-oxalocrotonate - ? 419261 5.3.2.6 2-hydroxymuconate stereospecific ketonization Pseudomonas putida 2-oxo-3-(E)-hexenedioate - ? 419909 5.3.2.6 2-hydroxymuconate stereospecific ketonization, a reaction of EC 5.3.2.6, is also catalyzed by 5-(carboxymethyl)-2-hydroxymuconate isomerase, EC 5.3.3.10 Escherichia coli 2-oxo-3-(E)-hexenedioate - ? 419909 5.3.2.6 2-hydroxymuconate stereospecific ketonization Pseudomonas putida mt-2 / ATCC 33015 / DSM 3931 / NCIB 12182 / NCIMB 12182 2-oxo-3-(E)-hexenedioate - ? 419909 5.3.2.6 2-hydroxymuconate stereospecific ketonization, a reaction of EC 5.3.2.6, is also catalyzed by 5-(carboxymethyl)-2-hydroxymuconate isomerase, EC 5.3.3.10 Escherichia coli C 2-oxo-3-(E)-hexenedioate - ? 419909 5.3.2.6 2-methoxy-5-[(Z)-2-nitroethenyl]phenol + acetaldehyde - Escherichia coli 3-(3-hydroxy-4-methoxyphenyl)-4-nitrobutanal - ? 427917 5.3.2.6 2-oxo-3-hexenedioate - Pseudomonas putida 2-oxo-3-trans-hexenedioate - ? 419924 5.3.2.6 2-oxo-3-hexenedioate - Pseudomonas putida mt-2 / ATCC 33015 / DSM 3931 / NCIB 12182 / NCIMB 12182 2-oxo-3-trans-hexenedioate - ? 419924 5.3.2.6 2-oxo-4(E)-hexenedioate 1,3-allylic isomerization Pseudomonas putida 2-oxo-3(E)-hexenedioate - ? 419263 5.3.2.6 2-oxo-4(E)-hexenedioate 1,3-allylic isomerization Pseudomonas putida mt-2 / ATCC 33015 / DSM 3931 / NCIB 12182 / NCIMB 12182 2-oxo-3(E)-hexenedioate - ? 419263 5.3.2.6 2-oxo-4-hexenedioate isomerization of unconjugated 2-oxo acids such as 2-oxo-4-hexenedioate, to its conjugated isomer via dienol intermediate 2-hydroxy-2,4-hexadienedioate, i.e. 2-hydroxymuconate Pseudomonas putida 2-oxo-3-hexenedioate - ? 419264 5.3.2.6 2-oxo-4-hexenedioate ketonization process via dienol intermediate 2-hydroxymuconate and with Pro1 as a general base, one-proton transfer mechanism Pseudomonas putida 2-oxo-3-hexenedioate - ? 419264 5.3.2.6 2-oxo-4-hexenedioate via dienol intermediate 2-hydroxymuconate Pseudomonas putida 2-oxo-3-hexenedioate - ? 419264 5.3.2.6 2-oxo-4-hexenedioate via the intermediate 2-hydroxy-2,4-hexadienedioate, i.e. 2-hydroxymuconate Pseudomonas putida 2-oxo-3-hexenedioate - ? 419264 5.3.2.6 2-oxo-4-hexenedioate the enzyme converts the unconjugated enone to the conjugated enone via a dienolic intermediate 2-hydroxymuconate, Pro1 serves as the general base, and both Arg11 and Arg39 function in substrate binding and catalysis in an otherwise hydrophobic active site. Anticooperativity during catalysis Pseudomonas putida 2-oxo-3-hexenedioate - r 419264 5.3.2.6 2-oxo-4-hexenedioate isomerization of unconjugated 2-oxo acids such as 2-oxo-4-hexenedioate, to its conjugated isomer via dienol intermediate 2-hydroxy-2,4-hexadienedioate, i.e. 2-hydroxymuconate Pseudomonas putida mt-2 / ATCC 33015 / DSM 3931 / NCIB 12182 / NCIMB 12182 2-oxo-3-hexenedioate - ? 419264 5.3.2.6 2-oxo-4-hexenedioate via dienol intermediate 2-hydroxymuconate Pseudomonas putida mt-2 / ATCC 33015 / DSM 3931 / NCIB 12182 / NCIMB 12182 2-oxo-3-hexenedioate - ? 419264 5.3.2.6 2-oxo-4-hexenedioate via the intermediate 2-hydroxy-2,4-hexadienedioate, i.e. 2-hydroxymuconate Pseudomonas putida mt-2 / ATCC 33015 / DSM 3931 / NCIB 12182 / NCIMB 12182 2-oxo-3-hexenedioate - ? 419264 5.3.2.6 2-oxopent-4-enoate - Pseudomonas putida 2-hydroxy-2,4-pentadienoate - ? 427942 5.3.2.6 3,4-(methylenedioxy)-beta-nitrostyrene + isobutanal - Pseudomonas putida (3E)-3-(2H-1,3-benzodioxol-5-yl)-2,2-dimethyl-4-nitrobut-3-enal - ? 444671 5.3.2.6 4-chloro-beta-nitrostyrene + acetaldehyde - Pseudomonas putida 3-(4-chlorophenyl)-4-nitrobutanal 38% yield ? 428027 5.3.2.6 4-fluoro-beta-nitrostyrene + acetaldehyde - Pseudomonas putida 3-(4-fluorophenyl)-4-nitrobutanal 31% yield ? 428036 5.3.2.6 4-vinyl-2,3-dihydropyrrole-2-carboxylic acid - Pseudomonas putida 4-ethylidene-3,4-dihydropyrrole-2-carboxylic acid - r 428064 5.3.2.6 5-(methyl)-2-hydroxymuconate - Methylibium petroleiphilum 5-(methyl)-2-oxo-3-hexenedioate - ? 428100 5.3.2.6 acetaldehyde + (1Z)-4-methyl-1-nitropent-1-ene - Pseudomonas putida 6-methyl-4-(nitromethyl)heptan-2-one - r 444862 5.3.2.6 acetaldehyde + 1-chloro-4-[(E)-2-nitroethenyl]benzene - Pseudomonas putida 4-(4-chlorophenyl)-5-nitropentan-2-one - r 444863 5.3.2.6 acetaldehyde + 1-fluoro-4-[(E)-2-nitroethenyl]benzene - Pseudomonas putida 4-(4-fluorophenyl)-5-nitropentan-2-one - r 444864 5.3.2.6 acetaldehyde + 2-(cyclopentyloxy)-1-methoxy-4-[(E)-2-nitroethenyl]benzene - Pseudomonas putida 4-[3-(cyclopentyloxy)-4-methoxyphenyl]-5-nitropentan-2-one - r 444865 5.3.2.6 acetaldehyde + 2-methoxy-5-[(E)-2-nitroethenyl]phenol - Pseudomonas putida 4-(3-hydroxy-4-methoxyphenyl)-5-nitropentan-2-one - r 444866 5.3.2.6 acetaldehyde + 4-[(E)-2-nitroethenyl]phenol - Pseudomonas putida 4-(4-hydroxyphenyl)-5-nitropentan-2-one - r 444867 5.3.2.6 acetaldehyde + benzaldehyde - Pseudomonas putida cinnamaldehyde - r 444869 5.3.2.6 acetaldehyde + [(E)-2-nitroethenyl]benzene - Pseudomonas putida 5-nitro-4-phenylpentan-2-one - r 444871 5.3.2.6 acetaldehyde + [(Z)-2-nitroethenyl]benzene - Bacillus subtilis (3S)-4-nitro-3-phenylbutanal - ? 428126 5.3.2.6 beta-nitrostyrene + acetaldehyde - Pseudomonas putida 4-nitro-3-phenyl-butanal 60% yield ? 428442 5.3.2.6 beta-nitrostyrene + acetaldehyde - Pseudomonas putida 4-nitro-3-phenylbutanal - r 445277 5.3.2.6 beta-nitrostyrene + isobutanal - Pseudomonas putida 2,2-dimethyl-4-nitro-3-phenylbutanal - ? 445278 5.3.2.6 butanal + [(E)-2-nitroethenyl]benzene - Pseudomonas putida 3-ethyl-5-nitro-4-phenylpentan-2-one - r 445283 5.3.2.6 butanal + [(Z)-2-nitroethenyl]benzene - Bacillus subtilis (2R,3S)-2-ethyl-4-nitro-3-phenylbutanal - ? 428454 5.3.2.6 heptanal + [(Z)-2-nitroethenyl]benzene - Bacillus subtilis (2R)-2-[(1S)-2-nitro-1-phenylethyl]heptanal - ? 428681 5.3.2.6 hexanal + [(Z)-2-nitroethenyl]benzene - Bacillus subtilis (2R)-2-[(1S)-2-nitro-1-phenylethyl]hexanal - ? 428685 5.3.2.6 isobutanal + beta-nitrostyrene - Pseudomonas putida 2,2-dimethyl-4-nitro-3-phenylbutanal + 4-nitro-3-phenylbutanal - ? 445568 5.3.2.6 additional information substrate specificity, overview Pseudomonas putida ? - ? 89 5.3.2.6 additional information substrate specificity, overview Pseudomonas sp. ? - ? 89 5.3.2.6 additional information 4-oxalocrotonate tautomerase catalyzes the isomerization of unsaturated 2-oxo acids, converting unconjugated ketones to the conjugated isomers via a dienolic intermediate Pseudomonas sp. ? - ? 89 5.3.2.6 additional information hh4-OT does not exhibit the low-level activity of another tautomerase superfamily member, the heterohexamer trans-3-chloroacrylic acid dehalogenase, no activity with trans-3-chloroacrylic acid Chloroflexus aurantiacus ? - ? 89 5.3.2.6 additional information ketonization of two monoacid substrates, 2-hydroxy-2,4-pentadienoate and phenylenolpyruvate, produces a mixture of stereoisomers, 2-keto-3-[2H]-4-pentenoate and 3-[2H]-phenylpyruvate, where the (3R)-isomers predominate Pseudomonas putida ? - ? 89 5.3.2.6 additional information the achiral substrate 2-hydroxymuconate is processed with equal efficiency by either the D- or the L-enzyme, stereochemical analysis of the D-4OT-catalyzed reaction, overviewn Pseudomonas putida ? - ? 89 5.3.2.6 additional information YwhB has a relatively non-specific 1,3- and 1,5-keto-enol tautomerase activity, converting 2-hydroxy-2,4-pentadienoate to 2-oxo-4-pentenoate, and phenylenolpyruvate to phenylpyruvate. But YwhB is a more efficient 1,3-keto-enol tautomerase than it is a 1,5-keto-enol tautomerase, and residues Pro-1 and Arg-11 are critical residues for these two activities Bacillus subtilis ? - ? 89 5.3.2.6 additional information no activity with (E)-2-cyclohexyl-1-nitroethene Pseudomonas putida ? - ? 89 5.3.2.6 additional information the enzyme also has a low level trans-3-chloroacrylic acid dehalogenase activity Pseudomonas putida ? - ? 89 5.3.2.6 additional information hh4-OT does not exhibit the low-level activity of another tautomerase superfamily member, the heterohexamer trans-3-chloroacrylic acid dehalogenase, no activity with trans-3-chloroacrylic acid Chloroflexus aurantiacus J-10-fl ? - ? 89 5.3.2.6 additional information ketonization of two monoacid substrates, 2-hydroxy-2,4-pentadienoate and phenylenolpyruvate, produces a mixture of stereoisomers, 2-keto-3-[2H]-4-pentenoate and 3-[2H]-phenylpyruvate, where the (3R)-isomers predominate Pseudomonas putida mt-2 / ATCC 33015 / DSM 3931 / NCIB 12182 / NCIMB 12182 ? - ? 89 5.3.2.6 additional information substrate specificity, overview Pseudomonas putida mt-2 / ATCC 33015 / DSM 3931 / NCIB 12182 / NCIMB 12182 ? - ? 89 5.3.2.6 additional information the achiral substrate 2-hydroxymuconate is processed with equal efficiency by either the D- or the L-enzyme, stereochemical analysis of the D-4OT-catalyzed reaction, overviewn Pseudomonas putida mt-2 / ATCC 33015 / DSM 3931 / NCIB 12182 / NCIMB 12182 ? - ? 89 5.3.2.6 additional information 4-oxalocrotonate tautomerase catalyzes the isomerization of unsaturated 2-oxo acids, converting unconjugated ketones to the conjugated isomers via a dienolic intermediate Pseudomonas sp. CF 600 ? - ? 89 5.3.2.6 additional information substrate specificity, overview Pseudomonas sp. CF 600 ? - ? 89 5.3.2.6 octanal + [(Z)-2-nitroethenyl]benzene - Bacillus subtilis (2R)-2-[(1S)-2-nitro-1-phenylethyl]octanal - ? 428857 5.3.2.6 pentanal + [(Z)-2-nitroethenyl]benzene - Bacillus subtilis (2R)-2-[(1S)-2-nitro-1-phenylethyl]pentanal - ? 428868 5.3.2.6 phenylenolpyruvate - Bacillus subtilis phenylpyruvate - ? 401641 5.3.2.6 phenylenolpyruvate - Helicobacter pylori phenylpyruvate - ? 401641 5.3.2.6 phenylenolpyruvate - Chloroflexus aurantiacus phenylpyruvate - r 401641 5.3.2.6 phenylenolpyruvate - Archaeoglobus fulgidus phenylpyruvate - ? 401641 5.3.2.6 phenylenolpyruvate - Pseudomonas putida phenylpyruvate - r 401641 5.3.2.6 phenylenolpyruvate - Chloroflexus aurantiacus J-10-fl phenylpyruvate - r 401641 5.3.2.6 propanal + [(Z)-2-nitroethenyl]benzene - Bacillus subtilis (2R,3S)-2-methyl-4-nitro-3-phenylbutanal - ? 428890 5.3.2.6 trans-p-chloro-beta-nitrostyrene + isobutanal - Pseudomonas putida 3-(4-chlorophenyl)-2,2-dimethyl-4-nitrobutanal - ? 445916 5.3.2.6 [(Z)-2-nitroethenyl]benzene + acetaldehyde - Escherichia coli 4-nitro-3-phenylbutanal - ? 429010