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Ligand hydrogen cyanide
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Basic Ligand Information
CHN, CN-, cyanide, cyanide (anion), formonitrile, HCN, HCN-, hydrocyanic acid, methanenitrile
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Show all BRENDA pathways known for hydrogen cyanide
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open all tablesRoles as Enzyme Ligand
In Vivo Substrate in Enzyme-catalyzed Reactions (19 results)
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EC NUMBER 
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
thiosulfate + cyanide = sulfite + thiocyanate
645514, 645546, 645500, 737706, 645534, 645536, 645537, 645539, 738551, 739155, 645532, 645533, 645495, 645535, 645511, 645540, 645501, 645503, 645504, 645505, 645506, 645507, 645508, 645510, 645519, 645522, 645524, 645525, 645526, 645527, 645528, 645529, 645531, 645543, 645545, 645542, 645497, 645515, 645496, 645521, 645523, 645516, 645530, 739474, 645499, 645541, 645512, 645513, 645498, 645517, 645520, 645509, 645544, 645518, 645502, 645538, 661492, 663433, 690262
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3-mercaptopyruvate + cyanide = pyruvate + thiocyanate
723958, 724194, 645548, 645495, 645559, 713731, 725310, 645547, 645550, 645551, 645554, 645561, 645562, 645564, 645552, 645553, 645556, 645557, 645566, 645567, 645560, 645558, 645498, 645565, 645569, 738551, 739651, 739661, 645563, 738988, 739470, 645568, 725528, 738634
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L-cysteine + HCN = sulfide + L-3-cyanoalanine
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L-cysteine + hydrogen cyanide = hydrogen sulfide + L-3-cyanoalanine
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In Vivo Product in Enzyme-catalyzed Reactions (21 results)
EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
1-aminocyclopropane-1-carboxylate + ascorbate + O2 + H+ = ethylene + cyanide + dehydroascorbate + CO2 + H2O
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1-aminocyclopropane-1-carboxylate + ascorbate + O2 = ethylene + cyanide + dehydroascorbate + CO2 + 2 H2O
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1-aminocyclopropane-1-carboxylate + ascorbate + O2 = ethylene + cyanide + dehydroascorbate + CO2 + H2O
639305, 639307, 639301, 0, 639300, 639299, 639302, 639310, 639312, 639303, 639308, 639309, 639298, 639296, 639297, 639304, 639311, 639306
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1-aminocyclopropane-1-carboxylic acid + ascorbate + O2 = ethylene + cyanide + dehydroascorbate + CO2 + H2O
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2-(L-cystein-S-yl)-2-(1H-indol-3-yl)acetonitrile + [reduced NADPH-hemoprotein reductase] + O2 = camalexin + hydrogen cyanide + CO2 + [oxidized NADPH-hemoprotein reductase] + H2O
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Substrate in Enzyme-catalyzed Reactions (487 results)
EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
reduced ferredoxin + H+ + CN- + ATP = oxidized ferredoxin + CH4 + NH3 + ADP + phosphate
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4-(dimethylamino)-4'-azobenzene thiosulfonate + cyanide = 4-(dimethylamino)-4'-azobenzene sulfinate + SCN-
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5-dimethylamino-1-naphthalene thiosulfonate + cyanide = 5-dimethylamino-1-naphthalene sulfinate + SCN-
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thiosulfate + cyanide = sulfite + thiocyanate
645514, 645546, 645500, 645502, 737706, 645534, 645536, 645537, 645538, 645539, 738551, 739155, 645518, 645532, 645533, 645495, 645535, 677214, 645511, 645540, 645501, 645503, 645504, 645505, 645506, 645507, 645508, 645510, 645519, 645522, 645524, 645525, 645526, 645527, 645528, 645529, 645531, 645543, 645545, 673274, 675044, 645542, 645520, 660889, 661492, 645497, 645515, 690262, 645496, 645521, 645523, 645516, 645530, 739474, 645499, 645541, 645512, 645513, 645498, 645517, 673600, 724480, 662068, 760422, 645509, 645544, 762459, 761486, 663433
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3-mercaptopyruvate + cyanide = pyruvate + thiocyanate
723958, 724194, 645548, 645495, 645559, 713731, 725310, 645547, 645550, 645551, 645554, 645561, 645562, 645564, 645552, 645553, 645556, 645557, 645566, 645567, 645560, 645558, 645498, 645565, 645569, 738551, 739651, 739661, 645563, 738988, 739470, 645568, 725528, 738634, 762459
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cyanide + (4R)-2,2-dimethyl-1,3-dioxolane-4-carbaldehyde = (2S)-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl](hydroxy)ethanenitrile + (2R)-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl](hydroxy)ethanenitrile
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cyanide + (4R,5S)-2,2,5-trimethyl-1,3-dioxolane-4-carbaldehyde = (2S)-hydroxy-[(4S,5S)-2,2,5-trimethyl-1,3-dioxolan-4-yl]ethanenitrile + (2R)-hydroxy-[(4S,5S)-2,2,5-trimethyl-1,3-dioxolan-4-yl]ethanenitrile
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cyanide + (4R,5S)-2,2-dimethyl-5-phenyl-1,3-dioxolane-4-carbaldehyde = (2S)-[(4S,5S)-2,2-dimethyl-5-phenyl-1,3-dioxolan-4-yl](hydroxy)ethanenitrile + (2R)-[(4S,5S)-2,2-dimethyl-5-phenyl-1,3-dioxolan-4-yl](hydroxy)ethanenitrile
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cyanide + (4S)-2,2-dimethyl-1,3-dioxolane-4-carbaldehyde = (2S)-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl](hydroxy)ethanenitrile + (2R)-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl](hydroxy)ethanenitrile
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cyanide + (4S,5R)-2,2,5-trimethyl-1,3-dioxolane-4-carbaldehyde = (2S)-hydroxy-[(4R,5R)-2,2,5-trimethyl-1,3-dioxolan-4-yl]ethanenitrile + (2R)-hydroxy-[(4R,5R)-2,2,5-trimethyl-1,3-dioxolan-4-yl]ethanenitrile
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cyanide + (4S,5R)-2,2-dimethyl-5-phenyl-1,3-dioxolane-4-carbaldehyde = (2S)-[(4R,5R)-2,2-dimethyl-5-phenyl-1,3-dioxolan-4-yl](hydroxy)ethanenitrile + (2R)-[(4R,5R)-2,2-dimethyl-5-phenyl-1,3-dioxolan-4-yl](hydroxy)ethanenitrile
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cyanide + (benzyloxy)acetaldehyde = (2R)-3-(benzyloxy)-2-hydroxypropanenitrile + (2S)-3-(benzyloxy)-2-hydroxypropanenitrile
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cyanide + 1,4-dioxaspiro[4.5]decane-2-carbaldehyde = (S)-2-hydroxy-2-((R)-1,4-dioxaspiro[4.5]decan-2-yl)acetonitrile + (R)-2-hydroxy-2-((R)-1,4-dioxaspiro[4.5]decan-2-yl)acetonitrile + (S)-2-hydroxy-2-((S)-1,4-dioxaspiro[4.5]decan-2-yl)acetonitrile + (R)-2-hydroxy-2-((S)-1,4-dioxaspiro[4.5]decan-2-yl)acetonitrile
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cyanide + 2,3,4a,8a-tetrahydro-1,4-benzodioxine-6-carbaldehyde = (2R)-hydroxy(2,3,4a,8a-tetrahydro-1,4-benzodioxin-6-yl)acetonitrile
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cyanide + 2,4-dimethylbenzaldehyde = (R)-2-hydroxy-2-(2,4-dimethylphenyl)acetonitrile
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cyanide + 2-(benzyloxy)-3-phenylpropanal = (2S,3S)-3-(benzyloxy)-2-hydroxy-4-phenylbutanenitrile + (2R,3S)-3-(benzyloxy)-2-hydroxy-4-phenylbutanenitrile + (2S,3R)-3-(benzyloxy)-2-hydroxy-4-phenylbutanenitrile + (2R,3R)-3-(benzyloxy)-2-hydroxy-4-phenylbutanenitrile
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cyanide + 2-(benzyloxy)propanal = (2S,3S)-3-(benzyloxy)-2-hydroxybutanenitrile + (2S,3S)-3-(benzyloxy)-2-hydroxybutanenitrile + (2S,3S)-3-(benzyloxy)-2-hydroxybutanenitrile + (2S,3S)-3-(benzyloxy)-2-hydroxybutanenitrile
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cyanide + 2-(naphthalen-2-yl)propanal = (2S,3S)-2-hydroxy-3-(naphthalen-2-yl)butanenitrile + (2S,3R)-2-hydroxy-3-(naphthalen-2-yl)butanenitrile + (2R,3S)-2-hydroxy-3-(naphthalen-2-yl)butanenitrile + (2R,3R)-2-hydroxy-3-(naphthalen-2-yl)butanenitrile
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cyanide + 2-chlorobenzaldehyde = (2R)-(2-chlorophenyl)(hydroxy)ethanenitrile
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cyanide + 2-chlorobenzaldehyde = (R)-2-chloromandelonitrile
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cyanide + 2-methoxy-3-phenylpropanal = (2S,3S)-2-hydroxy-3-methoxy-4-phenylbutanenitrile + (2R,3S)-2-hydroxy-3-methoxy-4-phenylbutanenitrile + (2S,3R)-2-hydroxy-3-methoxy-4-phenylbutanenitrile + (2R,3R)-2-hydroxy-3-methoxy-4-phenylbutanenitrile
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cyanide + 2-phenylpropanal = (2R,3S)-2-hydroxy-3-phenylbutanenitrile + (2S,3R)-2-hydroxy-3-phenylbutanenitrile + (2R,3R)-2-hydroxy-3-phenylbutanenitrile
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cyanide + 3,4-dihydro-1H-isochromene-3-carbaldehyde = (S)-2-hydroxy-2-((S)-isochroman-3-yl)acetonitrile + (S)-2-hydroxy-2-((R)-isochroman-3-yl)acetonitrile + (R)-2-hydroxy-2-((S)-isochroman-3-yl)acetonitrile + (R)-2-hydroxy-2-((R)-isochroman-3-yl)acetonitrile
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cyanide + 3,4-dihydroxybenzaldehyde = (R)-3,4-dihydroxymandelonitrile
-
cyanide + 3-hydroxy-2,2-dimethylpropanal = (2R)-2,5-dihydroxy-3,3-dimethylpentanenitrile
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cyanide + 3-methoxy-3-phenylpropanal = (2S,4S)-2-hydroxy-4-methoxy-4-phenylbutanenitrile + (2R,4S)-2-hydroxy-4-methoxy-4-phenylbutanenitrile + (2S,4R)-2-hydroxy-4-methoxy-4-phenylbutanenitrile + (2R,4R)-2-hydroxy-4-methoxy-4-phenylbutanenitrile
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cyanide + 3-tetrahydrothiophenone = (S)-3-hydroxytetrahydrothiophene-3-carbonitrile
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cyanide + 4-bromobenzaldehyde = (2R)-(4-bromophenyl)(hydroxy)ethanenitrile
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cyanide + 4-methoxybenzaldehyde = (2R)-(4-methoxyphenyl)(hydroxy)ethanenitrile
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cyanide + 4-methylbenzaldehyde = (2R)-(4-methylphenyl)(hydroxy)ethanenitrile
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cyanide + benzaldehyde = (R)-mandelonitrile
651014, 691796, 703209, 746692, 650926, 714536, 663422, 691375, 702292, 715946, 728160, 748401, 749351, 747750, 747326, 747553, 653959, 701695, 37319, 662667, 727481, 726720, 705191, 703501, 702798, 746785, 747948, 747398, 747465, 747466, 749169, 747548
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cyanide + naphthalen-2-ylacetaldehyde = (2R)-2-hydroxy-3-(naphthalen-2-yl)propanenitrile
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cyanide + naphthalen-2-ylacetaldehyde = (2R)-2-hydroxy-3-(naphthalen-2-yl)propanenitrile + (2S)-2-hydroxy-3-(naphthalen-2-yl)propanenitrile
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cyanide + phenylacetaldehyde = (2R)-2-hydroxy-3-phenylpropanenitrile
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cyanide + tetrahydro-2H-pyran-2-carbaldehyde = (2S)-hydroxy-[(2R)-tetrahydro-2H-pyran-2-yl]ethanenitrile + (2R)-hydroxy-[(2R)-tetrahydro-2H-pyran-2-yl]ethanenitrile + (2S)-hydroxy-[(2S)-tetrahydro-2H-pyran-2-yl]ethanenitrile + (2R)-hydroxy-[(2S)-tetrahydro-2H-pyran-2-yl]ethanenitrile
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cyanide + tetrahydrofuran-2-carbaldehyde = (2S)-hydroxy-[(2R)-tetrahydrofuran-2-yl]ethanenitrile + (2R)-hydroxy-[(2R)-tetrahydrofuran-2-yl]ethanenitrile + (2S)-hydroxy-[(2S)-tetrahydrofuran-2-yl]ethanenitrile + (2R)-hydroxy-[(2S)-tetrahydrofuran-2-yl]ethanenitrile
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HCN + 2,3,4,5-tetrafluorobenzaldehyde = (R)-2-hydroxy-2-(2,3,4,5-tetrafluorophenyl)acetonitrile
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HCN + 2,3,4-trimethoxybenzaldehyde = (R)-2-hydroxy-2-(2,3,4-trimethoxyphenyl)acetonitrile
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HCN + 2,3,5,6-tetrafluorobenzaldehyde = (R)-2-hydroxy-2-(2,3,5,6-tetrafluorophenyl)acetonitrile
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HCN + 2,3,5-trimethoxybenzaldehyde = (R)-2-hydroxy-2-(2,3,5-trimethoxyphenyl)acetonitrile
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HCN + 2,3-dimethoxybenzaldehyde = (R)-2-hydroxy-2-(2,3-dimethoxyphenyl)acetonitrile
-
HCN + 2,4-dimethoxybenzaldehyde = (R)-2-hydroxy-2-(2,4-dimethoxyphenyl)acetonitrile
-
HCN + 2,5-dimethoxybenzaldehyde = (R)-2-hydroxy-2-(2,5-dimethoxyphenyl)acetonitrile
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HCN + 2,6-dimethoxybenzaldehyde = (R)-2-hydroxy-2-(2,6-dimethoxyphenyl)acetonitrile
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HCN + 2-allylcyclohexanone = trans-(1R,2R)-1-hydroxy-2-allylcyclohexanecarbonitrile
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HCN + 2-allyloxycyclohexanone = cis-(1S,2S)-1-hydroxy-2-allyloxycyclohexanecarbonitrile
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HCN + 2-allyloxycyclohexanone = trans-(1S,2R)-1-hydroxy-2-allyloxycyclohexanecarbonitrile
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HCN + 2-ethoxycyclohexanone = cis-(1S,2S)-1-hydroxy-2-ethoxycyclohexanecarbonitrile
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HCN + 2-ethoxycyclohexanone = trans-(1S,2R)-1-hydroxy-2-ethoxycyclohexanecarbonitrile
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HCN + 2-ethylcyclohexanone = trans-(1R,2R)-1-hydroxy-2-methylcyclohexanecarbonitrile
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HCN + 2-methoxycyclohexanone = cis-(1S,2S)-1-hydroxy-2-methoxycyclohexanecarbonitrile
-
HCN + 2-methoxycyclohexanone = trans-(1S,2R)-1-hydroxy-2-methoxycyclohexanecarbonitrile
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HCN + 2-methylcyclohexanone = cis-(1R,2S)-1-hydroxy-2-methylcyclohexanecarbonitrile
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HCN + 2-methylcyclohexanone = trans-(1R,2R)-1-hydroxy-2-methylcyclohexanecarbonitrile
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HCN + 2-n-propoxycyclohexanone = cis-(1S,2S)-1-hydroxy-2-n-propoxycyclohexanecarbonitrile
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HCN + 2-n-propoxycyclohexanone = trans-(1S,2R)-1-hydroxy-2-n-propoxycyclohexanecarbonitrile
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HCN + 2-n-propylcyclohexanone = cis-(1R,2S)-1-hydroxy-2-n-propylcyclohexanecarbonitrile
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HCN + 2-n-propylcyclohexanone = trans-(1R,2R)-1-hydroxy-2-n-propylcyclohexanecarbonitrile
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HCN + 2-trifluoromethylbenzaldehyde = (R)-2-hydroxy-2-(2-trifluoromethylphenyl)acetonitrile
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HCN + 3,4,5-trimethoxybenzaldehyde = (R)-2-hydroxy-2-(3,4,5-trimethoxyphenyl)acetonitrile
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HCN + 3,4-dimethoxybenzaldehyde = (R)-2-hydroxy-2-(3,4-dimethoxyphenyl)acetonitrile
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HCN + 3,5-dimethoxybenzaldehyde = (R)-2-hydroxy-2-(3,5-dimethoxyphenyl)acetonitrile
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HCN + 3-methoxycyclohexanone = cis-(1R,3S)-1-hydroxy-3-methoxycyclohexanecarbonitrile
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HCN + 3-methoxycyclohexanone = trans-(1R,3R)-1-hydroxy-3-methoxycyclohexanecarbonitrile
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HCN + 3-methylcyclohexanone = cis-(1R,3S)-1-hydroxy-3-methylcyclohexanecarbonitrile
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HCN + 3-methylcyclohexanone = trans-(1R,3R)-1-hydroxy-3-methylcyclohexanecarbonitrile
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HCN + 3-trifluoromethylbenzaldehyde = (R)-2-hydroxy-2-(3-trifluoro-methylphenyl)acetonitrile
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HCN + 3-trifluoromethylcyclohexanone = cis-(1R,3S)-1-hydroxy-3-trifluoromethylcyclohexanecarbonitrile
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HCN + 3-trifluoromethylcyclohexanone = trans-(1R,3R)-1-hydroxy-3-trifluoromethylcyclohexanecarbonitrile
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HCN + 4-tert-butyldimethylsilyloxybenzaldehyde = (R)-2-hydroxy-2-(4-tert-butyldimethylsilyloxyphenyl)acetonitrile
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HCN + 4-trifluoromethylbenzaldehyde = (R)-2-hydroxy-2-(4-trifluoromethylphenyl)acetonitrile
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HCN + iso-propoxycyclohexanone = cis-(1S,2S)-1-hydroxy-2-iso-propoxycyclohexanecarbonitrile
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HCN + iso-propoxycyclohexanone = trans-(1S,2R)-1-hydroxy-2-iso-propoxycyclohexanecarbonitrile
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cyanide + (2E)-3-(4-hydroxyphenyl)prop-2-enal = (2S,3E)-2-hydroxy-4-(4-hydroxyphenyl)but-3-enenitrile
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cyanide + (4-hydroxyphenyl)acetaldehyde = (2S)-2-hydroxy-3-(4-hydroxyphenyl)propanenitrile
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cyanide + (4R)-2,2-dimethyl-1,3-dioxolane-4-carbaldehyde = (2S)-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl](hydroxy)ethanenitrile + (2R)-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl](hydroxy)ethanenitrile
-
cyanide + (4R,5S)-2,2,5-trimethyl-1,3-dioxolane-4-carbaldehyde = (2S)-hydroxy-[(4S,5S)-2,2,5-trimethyl-1,3-dioxolan-4-yl]ethanenitrile + (2R)-hydroxy-[(4S,5S)-2,2,5-trimethyl-1,3-dioxolan-4-yl]ethanenitrile
-
cyanide + (4R,5S)-2,2-dimethyl-5-phenyl-1,3-dioxolane-4-carbaldehyde = (2S)-[(4S,5S)-2,2-dimethyl-5-phenyl-1,3-dioxolan-4-yl](hydroxy)ethanenitrile + (2R)-[(4S,5S)-2,2-dimethyl-5-phenyl-1,3-dioxolan-4-yl](hydroxy)ethanenitrile
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cyanide + (4S)-2,2-dimethyl-1,3-dioxolane-4-carbaldehyde = (2S)-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl](hydroxy)ethanenitrile + (2R)-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl](hydroxy)ethanenitrile
-
cyanide + (4S,5R)-2,2,5-trimethyl-1,3-dioxolane-4-carbaldehyde = (2S)-hydroxy-[(4R,5R)-2,2,5-trimethyl-1,3-dioxolan-4-yl]ethanenitrile + (2R)-hydroxy-[(4R,5R)-2,2,5-trimethyl-1,3-dioxolan-4-yl]ethanenitrile
-
cyanide + (4S,5R)-2,2-dimethyl-5-phenyl-1,3-dioxolane-4-carbaldehyde = (2S)-[(4R,5R)-2,2-dimethyl-5-phenyl-1,3-dioxolan-4-yl](hydroxy)ethanenitrile + (2R)-[(4R,5R)-2,2-dimethyl-5-phenyl-1,3-dioxolan-4-yl](hydroxy)ethanenitrile
-
cyanide + 1,3-benzodioxole-5-carbaldehyde = (2S)-1,3-benzodioxol-5-yl(hydroxy)acetonitrile
-
cyanide + 1,4-dioxaspiro[4.5]decane-2-carbaldehyde = (S)-2-hydroxy-2-((R)-1,4-dioxaspiro[4.5]decan-2-yl)acetonitrile + (R)-2-hydroxy-2-((R)-1,4-dioxaspiro[4.5]decan-2-yl)acetonitrile + (S)-2-hydroxy-2-((S)-1,4-dioxaspiro[4.5]decan-2-yl)acetonitrile + (R)-2-hydroxy-2-((S)-1,4-dioxaspiro[4.5]decan-2-yl)acetonitrile
-
cyanide + 2,4-dimethylbenzaldehyde = (2S)-(2,4-dimethylphenyl)(hydroxy)ethanenitrile
-
cyanide + 3-(4-hydroxyphenyl)propanal = (2S)-2-hydroxy-4-(4-hydroxyphenyl)butanenitrile
-
cyanide + 3-tetrahydrothiophenone = (S)-3-hydroxytetrahydrothiophene-3-carbonitrile
-
cyanide + 4-methoxycyclohex-3-ene-1-carbaldehyde = (2S)-hydroxy[4-(methoxy)cyclohex-3-en-1-yl]ethanenitrile
-
cyanide + 4-oxocyclohexanecarbaldehyde = (2S)-hydroxy(4-oxocyclohexyl)ethanenitrile
-
cyanide + 4-[(trimethylsilyl)oxy]cyclohex-3-ene-1-carbaldehyde = (2S)-hydroxy[4-((trimethylsilyl)oxy)cyclohex-3-en-1-yl]ethanenitrile
-
cyanide + benzaldehyde = (S)-mandelonitrile
691761, 711749, 684655, 704762, 713464, 747927, 716823, 747534, 5154, 5153, 650854, 714712, 728015, 691373, 746690
-
cyanide + cyclohex-3-ene-1-carbaldehyde = (2S)-2-(cyclohex-3-enyl)-2-hydroxyacetonitrile
-
cyanide + tetrahydro-2H-pyran-2-carbaldehyde = (2S)-hydroxy-[(2R)-tetrahydro-2H-pyran-2-yl]ethanenitrile + (2R)-hydroxy-[(2R)-tetrahydro-2H-pyran-2-yl]ethanenitrile + (2S)-hydroxy-[(2S)-tetrahydro-2H-pyran-2-yl]ethanenitrile + (2R)-hydroxy-[(2S)-tetrahydro-2H-pyran-2-yl]ethanenitrile
-
cyanide + tetrahydrofuran-2-carbaldehyde = (2S)-hydroxy-[(2R)-tetrahydrofuran-2-yl]ethanenitrile + (2R)-hydroxy-[(2R)-tetrahydrofuran-2-yl]ethanenitrile + (2S)-hydroxy-[(2S)-tetrahydrofuran-2-yl]ethanenitrile + (2R)-hydroxy-[(2S)-tetrahydrofuran-2-yl]ethanenitrile
-
HCN + (benzyloxy)acetaldehyde = 3-(benzyloxy)-(2S)-2-hydroxy-propanenitrile + 3-(benzyloxy)-(2R)-2-hydroxy-propanenitrile
-
HCN + 2-methyldihydrothiophen-3(2H)-one = 3-hydroxy-2-methyltetrahydrothiophen-3-carbonitrile
-
HCN + 2-naphthaldehyde = (2S)-2-hydroxynaphthalen-2-yl-acetonitrile + (2R)-2-hydroxynaphthalen-2-yl-acetonitrile
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HCN + 2-naphthylacetaldehyde = (2S)-2-hydroxy-3-naphthalen-1-yl-propionitrile + (2R)-2-hydroxy-3-naphthalen-1-yl-propionitrile
-
HCN + 3-phenoxypropanal = (2S)-2-hydroxy-4-phenoxybutanenitrile + (2S)-2-hydroxy-4-phenoxybutanenitrile
-
HCN + rac-2-methyl-3-phenylpropionaldehyde = (2S,3R)-2-hydroxy-3-methyl-4-phenylbutyronitrile
-
cyanide + 1,3-benzodioxole-5-carbaldehyde = (2S)-1,3-benzodioxol-5-yl(hydroxy)ethanenitrile
-
HCN + H2O = formamide
-
L-cysteine + HCN = H2S + L-3-cyanoalanine
34722, 34716, 34723, 34724, 34727, 34728, 34729, 34725, 34719, 34718, 34720, 34730, 34735, 34726, 704926, 34721, 706135, 34733, 34734, 34736, 34717, 34731, 34732, 682356
-
L-cysteine + HCN = sulfide + L-3-cyanoalanine
-
L-cysteine + hydrogen cyanide = hydrogen sulfide + L-3-cyanoalanine
-
Product in Enzyme-catalyzed Reactions (112 results)
EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
3,5-dibromo-4-hydroxybenzonitrile + 2 NADPH + 2 H+ + O2 = 2,6-dibromo-p-hydroquinone + CN- + 2 NADP+ + H2O
-
1-amino-2-ethylcyclopropane-1-carboxylate + L-ascorbate + O2 + HCO3- = 1-butene + cyanide + dehydroascorbate + CO2 + H2O
-
1-amino-2-ethylcyclopropane-1-carboxylate + L-ascorbate + O2 = 1-butene + cyanide + dehydroascorbate + CO2 + H2O
-
1-aminocyclopropane-1-carboxylate + 5,6-O-isopropylidine L-ascorbate + O2 = ethylene + cyanide + 5,6-O-isopropylidine L-dehydroascorbate + CO2 + H2O
-
1-aminocyclopropane-1-carboxylate + ascorbate + O2 + H+ = ethylene + cyanide + dehydroascorbate + CO2 + H2O
-
1-aminocyclopropane-1-carboxylate + ascorbate + O2 = ethylene + cyanide + dehydroascorbate + CO2 + 2 H2O
-
1-aminocyclopropane-1-carboxylate + ascorbate + O2 = ethylene + cyanide + dehydroascorbate + CO2 + H2O
639305, 639307, 639301, 0, 639300, 639299, 639302, 639310, 639312, 639303, 639308, 639309, 639298, 639296, 639297, 639304, 639311, 639306
-
1-aminocyclopropane-1-carboxylate + D-ascorbate + O2 = ethylene + cyanide + D-dehydroascorbate + CO2 + H2O
-
1-aminocyclopropane-1-carboxylate + L-ascorbate + O2 = ethylene + cyanide + dehydroascorbate + CO2 + H2O
639311, 639299, 639298, 639296, 639297, 639312, 639306, 639309, 639310, 639305, 639307, 639301, 639304, 639300, 639302, 639303, 639308
-
1-aminocyclopropane-1-carboxylic acid + ascorbate + O2 = ethylene + cyanide + dehydroascorbate + CO2 + H2O
-
2-(L-cystein-S-yl)-2-(1H-indol-3-yl)acetonitrile + [reduced NADPH-hemoprotein reductase] + O2 = camalexin + hydrogen cyanide + CO2 + [oxidized NADPH-hemoprotein reductase] + H2O
-
reduced ferredoxin + H+ + SCN- + ATP = oxidized ferredoxin + H2S + HCN + ADP + phosphate
-
glycine + 2,2'-di-(p-nitrophenyl-5,5')-(diphenyl)-3,3'-(3,3'-dimethoxy-4,4'-diphenylene) ditetrazolium chloride = HCN + ?
-
glycine + 2-(p-iodophenyl)-3-(p-nitrophenyl)-5-phenyl-tetrazolium chloride = HCN + CO2 + ?
-
deltamethrin + H2O = 3-phenoxybenzaldehyde + (1R,3R)-3-(2,2-dibromoethenyl)-2,2-dimethylcyclopropanecarboxylate + cyanide
-
(alphaR)-fenpropathrin + H2O = 3-phenoxybenzaldehyde + 2,2,3,3-tetramethylcyclopropanecarboxylate + cyanide
-
(alphaR,2R)-fenvalerate + H2O = 3-phenoxybenzaldehyde + (2R)-2-(4-chlorophenyl)-3-methylbutanoate + cyanide
-
(alphaR,2S)-fenvalerate + H2O = 3-phenoxybenzaldehyde + (2S)-2-(4-chlorophenyl)-3-methylbutanoate + cyanide
-
(alphaS)-fenpropathrin + H2O = 3-phenoxybenzaldehyde + 2,2,3,3-tetramethylcyclopropanecarboxylate + cyanide
-
(alphaS,2R)-fenvalerate + H2O = 3-phenoxybenzaldehyde + (2R)-2-(4-chlorophenyl)-3-methylbutanoate + cyanide
-
(alphaS,2S)-fenvalerate + H2O = 3-phenoxybenzaldehyde + (2S)-2-(4-chlorophenyl)-3-methylbutanoate + cyanide
-
cis-cypermethrin + H2O = 3-phenoxybenzaldehyde + (1S,3S)-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropanecarboxylate + cyanide
-
cyhalothrin + H2O = 3-phenoxybenzaldehyde + 3-[(1Z)-2-chloro-3,3,3-trifluoroprop-1-en-1-yl]-2,2-dimethylcyclopropanecarboxylate + cyanide
-
cypermethrin + H2O = 3-phenoxybenzaldehyde + 3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropanecarboxylate + cyanide
-
deltamethrin + H2O = 3-phenoxybenzaldehyde + (1R,3R)-3-(2,2-dibromoethenyl)-2,2-dimethylcyclopropanecarboxylate + cyanide
-
fenopropathrin + H2O = 3-phenoxybenzaldehyde + 2,2,3,3-tetramethylcyclopropanecarboxylate + cyanide
-
fenpropathrin + H2O = 3-phenoxybenzaldehyde + 2,2,3,3-tetramethylcyclopropanecarboxylate + cyanide
-
fenvalerate + H2O = 3-phenoxybenzaldehyde + 2-(4-chlorophenyl)-3-methylbutanoic acid + cyanide
-
sumicidin + H2O = 3-phenoxybenzaldehyde + 2-(4-chlorophenyl)-3-methylbutanoic acid + cyanide
-
trans-cypermethrin + H2O = 3-phenoxybenzaldehyde + (1S,3R)-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropanecarboxylate + cyanide
-
ethyl N,N-dimethylphosphoramidocyanidate + H2O = ethyl N,N-dimethylphosphoramide + cyanide
-
ethyl dimethylphosphoramidocyanidate + H2O = ethyl hydrogen dimethylphosphoramidate + HCN
-
(R)-alpha-[(6-O-beta-D-glucopyranosyl-beta-D-glucopyranosyl)oxy]benzeneacetonitrile + H2O = HCN + ?
-
cyano(2-methoxy-naphthalen-6-yl)methyl trans-2-(3-propyloxiran-2-yl) acetate + H2O = 6-methoxy-2-naphthaldehyde + CN- + ?
-
cyano(6-methoxy-2-naphthyl)methyl (3,3-dimethyloxiran-2-yl)methyl carbonate + H2O = 6-methoxy-2-naphthaldehyde + CN- + ?
-
cyano(6-methoxy-2-naphthyl)methyl (3-ethyloxiran-2-yl)methyl carbonate + H2O = 6-methoxy-2-naphthaldehyde + CN- + ?
-
cyano(6-methoxy-2-naphthyl)methyl (3-phenyloxiran-2-yl)acetate + H2O = 6-methoxy-2-naphthaldehyde + CN- + ?
-
cyano(6-methoxy-2-naphthyl)methyl (3-phenyloxiran-2-yl)methyl carbonate + H2O = 6-methoxy-2-naphthaldehyde + CN- + ?
-
cyano(6-methoxy-2-naphthyl)methyl (3-propyloxiran-2-yl)methyl carbonate + H2O = 6-methoxy-2-naphthaldehyde + CN- + ?
-
cyano(6-methoxy-2-naphthyl)methyl [3-(4-nitrophenyl)oxiran-2-yl]methyl carbonate + H2O = 6-methoxy-2-naphthaldehyde + CN- + ?
-
[3-(4-chlorophenyl)oxiran-2-yl]methyl cyano(6-methoxy-2-naphthyl)methyl carbonate + H2O = 6-methoxy-2-naphthaldehyde + CN- + ?
-
deltamethrin + H2O = 3-phenoxybenzaldehyde + (1R,3R)-3-(2,2-dibromoethenyl)-2,2-dimethylcyclopropanecarboxylate + cyanide
-
(S)-4-Hydroxymandelonitrile = Cyanide + 4-hydroxybenzaldehyde
-
Activator in Enzyme-catalyzed Reactions (25 results)
EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
suppresses the peculiar endogenous reaction of methanol dehydrogenase, and is also both an activator of substrate-dependent activity and a competitive inhibitor with respect to methanol, the two activities correspond to two distinct binding sites for cyanide, overview
-
stimulates D-lactate dehydrogenase activity at neutral pH, though it inhibits the activity at alkaline pH
-
the enzyme is activated by cyanide concentrations between 0.1 and 1 mM with most efficient activation at 0.5 mM
-
substrate binding is enhanced for metal-loaded enzymes that are supplied with cyanide
-
activates the enzyme in reaction with ferricytochrome c or ferricyanide as electron acceptors, but not with flavin D or FAd
-
SQR isolated from yeast mitochondria reduces decyl-ubiquinone after the addition of sulfide only in the presence of cyanide
-
Inhibitor in Enzyme-catalyzed Reactions (455 results)
EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
competitive with nicotinamide nucleotides. NADH increases cyanide-resistance of ADH II
-
suppresses the peculiar endogenous reaction of methanol dehydrogenase, and is also both an activator of substrate-dependent activity and a competitive inhibitor with respect to methanol, the two activities correspond to two distinct binding sites for cyanide, overview
-
stimulates D-lactate dehydrogenase activity at neutral pH, though it inhibits the activity at alkaline pH. At 1.5 mM, 50% inhibition at pH 9.3
-
cyanide inhibition occurs in both the oxidized and reduced state of 4-HBCR, in the reduced state 4-HBCR is reactivated by simple oxidation, in the oxidized state reactivation is only achieved in the presence of sulfide
-
0.165 mM, 84%, 70%, 100% and 40% inhibition of isoenzymes A, B, C and D, respectively
-
quinol oxidase activity of the membranes from the wild type shows a biphasic dependence on the cyanide concentration; quinol oxidase activity of the membranes from the wild type shows a biphasic dependence on the cyanide concentration
-
competitive. Inhibitor binding occurs at the low-potential heme active site, shifting the resulting catalytic midpoint potential in a negative direction
-
cyanide binding can act as a surrogate for the hydrogen peroxide reaction. Structural features that are important for accelerating cyanide binding are also important for accelerating the rate of hydrogen peroxide binding to the heme iron, equilibrium dissociation constants of wild-type and mutant enzymes, and pH-independent equilibrium dissociation constants for the high- and low-affinity cyanide binding phases of the triple mutants, overview
-
the W51H mutations have a weaker effect on cyanide binding, with the cyanide affinity only 2-8times weaker than for cytochrome c peroxidase. The cyanide association rate constants are between 5 and 85times slower for the W51H mutants, while the cyanide dissociation rate constants range from 3times slower to 6times faster than those of wild-type cytochrome c peroxidase
-
catalase activity at pH 4.5, in comparison to the other two pH optima at 6.5 and 10.0, has lowest sensitivity to cyanide
-
no inhibition if simultaneously incubated with 2-mercaptoethanol, glutathione or dithiothreitol
-
cyanide binds to either cysteamine- or Cys-bound Fe(III)ADO, binding causes the appearance of a dominant low-spin (S = 1/2) EPR signal and a small but noticeable change to the electronic absorption spectrum
-
prebinding of cyanide to the enzyme facilitates L-Trp binding by 22fold but retards its dissociation by 2fold, indicating that cyanide binding to the heme iron introduces structural changes to the protein matrix allowing faster access of the substrate to the active site and slower dissociation from it. Prebinding of L-Trp to the enzyme retards cyanide binding by about 13fold
-
iron chelator strongly inhibits enzyme in reconstituted in vitro assay but not or only slightly in intact chloroplast systems with membrane-bound haemoprotein
-
binding of cyanide results in significant conformational changes and two different rotamers for residue D251
-
0.2 mM, 70% inhibition of catechol oxidation, 63% inhibition of pyrogallol oxidation, 50% inhibition of dopa oxidation
-
cyanide treatment of the enzyme removes about 98% of the copper and about 49% of the iron and abolishes all activity
-
the enzyme inhibited by cyanide but not by carbon monoxide, indicating that it required cytochrome b5
-
contains a cyanide-sensitive enzyme in cytosol and mitochondrial intermembrane space and one cyanide-insensitive enzyme in mitochondrial matrix; Cu,Zn-SOD; no inhibition Mn-SOD
-
no inhibition
-
-
287889, 288085, 288086, 288092, 288093, 288098, 288104, 288109, 288110, 288112, 288115, 288117, 288123
-
irreversible inactivation at low concentrations, faster inactivation at more alkaline pH
-
the ability of AAO1 and AAO3 to reduce 2,6-dichloroindophenol is abrogated when the enzymes are pre-treated with cyanide, NADH oxidation activity of AAO1 and AAO3 is highly sensitive to cyanide treatment
-
molybdenum-containing enzymes are inactivated, tungsten-containing isoenzymes are not inactivated
-
0.2 mM, 17% inhibition in the presence of air, 32% CO and 69% N2, inhibition can be removed by O2 or CO
-
CO, CO2 and COS reverse inhibition; dithionite slows the inhibition, but cannot reactivate the enzyme
-
0.075 mM, reversible, competitive inhibition of reduced CODHII with respect to the substrate carbon monoxide, which protects reduced CODHII against inhibition by cyanide, inhibited CODHII regains initial activity after a 15-25-min incubation at 70°C with dithionite or Ti(III) citrate under CO or N2, while slower and partial reactivation to 30-50% of the initial activity occurs with dithiothreitol or without reductants
-
inactivates tungsten-containing enzyme, molybdenum-containing enzyme is insensitive
-
cyanide ion, membrane-bound enzyme, modest inhibition at high concentrations, greater than 1 mM, partial purified enzyme, sodium cyanide, no or very poor inhibition, 10 mM: 3.5% inhibition
-
inactivation by simultaneous presence of NADH and low concentrations of cyanide, reactivation by incubation with ferricyanide or by a short exposure to light in the presence of FAD
-
mechanism of reactivation of cyanide-inactivated nitrate reductase by flavins in light
-
reactivation by incubation with oxidant systems after inactivation by treatment with NADH and cyanide
-
1 mM, 45% inhibition, no inhibition if enzyme is preincubated with nitrite or NH2OH prior to adding the inhibitor
-
cyanide is a potent inhibitor of NrfA nitrite and hydroxylamine reductase activities
-
two sites for cyanide binding and inhibition, higher affinity of cyanide for reduced versus oxidized forms of nitrite reductase
-
addition of 0.035 mM, 0.085 mM, or 0.35 mM cyanide results in 25%, 50%, and 95% inhibition, respectively
-
inactivation of the enzyme by trapping of the electrophilic imine reaction intermediate, formation of a cyanoalkyl intermediate, reaction with the substrate after proton abstraction but before flavin oxidation
-
the presence of residue Phe159 enhances the interaction energy of the anion with the urate pi system
-
preincubating the enzyme with cyanide increases the extent of inhibition which in turn is intensified when dithionite is present. Although cyanide is a noncompetitive inhibitor with respect to nitrate, nitrate protects against inhibition
-
only when added with NADPH prior to substrate, sulfite prevents NADPH-reduced form from irreversible conversion by CN-; severe inhibition of NADPH-sulfite,-nitrite,-hydroxylamine reductase, no inhibition of methyl viologen-sulfite reductase, small extent of inhibition of NADPH dependent reduction of cytochrome c, ferricyanide, quinones etc.
-
severe inhibition of NADPH-sulfite,-nitrite,-hydroxylamine reductase, no inhibition of methyl viologen-sulfite reductase, small extent of inhibition of NADPH dependent reduction of cytochrome c, ferricyanide, quinones etc.
-
cyanide treatment destabilized human SQOR and leads to its inactivation with concomitant loss of the bridging sulfane sulfur. Addition of sulfide to inactive cyanide treated enzyme leads to recovery of active SQOR, indicating that the oxidation state of the active site cysteines is preserved upon cyanide treatment. Crystallization of SQOR with cyanide led to the capture of a 379Cys N-(201Cys-disulfanyl)-methanimido thioate intermediate. Spectral and kinetic characterization of cyanolysis-induced dismantling followed by sulfide-dependent rebuilding of the trisulfide cofactor, proposed mechanism for cyanolysis and cysteine trisulfide rebuilding in SQOR, overview
-
Tyr-sensitive isozyme, strong inhibition, reactivation by divalent cations only to a small extent
-
autokinase activity of the purified ethylene resistant 1 is completely abolished by 2 mM cyanide
-
inhibitory synergism between cyanide and carbonyl compounds. The effectiveness in descending order: acetaldehyde, acetone, cyclohexanone, methyl ethyl ketone, 3-hexanone, diethyl ketone
-
irreversible, in presence of aldehydes, reversible in abscence of aldehydes, 2-keto-4-hydroxyglutarate cleavage, Ki: 0.57 mM
-
irreversible, in presence of 4-hydroxy-2-oxoglutarate; irreversible loss of activity in presence of glyoxylate, but not in presence of pyruvate
-
-
-
2 mM, oxidation of caldariella quinol and N,N,N',N'-tetramethyl-1,4-phenylenediamine is completely inhibited
-
0.13 mM, 50% inhibition of horse cytochrome c oxidation, 0.08 mM 50% inhibition of horse and Candida krusei cytochrome c oxidation in the presence of cardiolipin, 0.06 mM, 50% inhibition of Candida krusei cytochrome c oxidation, 0.05 mM, 50% inhibition of Nitrosomonas europaea cytochrome c oxidation
-
Pseudomonas fluorescens strain CHA0 can kill Odontotermes obesus by inhibiting cytochrome c oxidase of the termite respiratory chain with the pseudomonad metabolite cyanide after a 2 h incubation period
-
Metals and Ions (17 results)
EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
enzyme contains four cyanides in its active site, one is bound to the Ni2+, the active site is a (enzyme-Cys)2(CN)Ni(micro-enzyme-Cys)2Fe(CN)3(CO) centre, the CN- bound to the nickel ion can be irreversibly removed inducing enzyme inhibition by oxygen
-
enzyme contains four cyanides in its active site, the Ni2+ bound one is responsible for the insensitivity towards oxygen, the active site is a (enzyme-Cys)2(CN)Ni(micro-enzyme-Cys)2Fe(CN)3(CO) centre, the CN- bound to the nickel ion can be irreversibly removed inducing enzyme inhibition by oxygen
-
enzyme contains four cyanides in its active site, one of which is responsible for the insensitivity towards oxygen
-
enhances the affinity for L-tryptophan for the ferric enzyme in reziprocal manner, positive cooperativity
-
Enzyme Kinetic Parameters
kcat Value (Turnover Number) (5 results)
EC NUMBER
TURNOVER NUMBER [1/S]
TURNOVER NUMBER MAXIMUM [1/S]
COMMENTARY
LITERATURE
KM Value (53 results)
EC NUMBER
KM VALUE [MM]
KM VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
Ki Value (53 results)
EC NUMBER
KI VALUE [MM]
KI VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
0.05
-
pH 7, 25 microM H2O2, protein film voltammetry, the midpoint potentials of the turnover signals are used to calculate Michaelis-Menten kinetics
0.68
-
Zn(II)-substituted enzyme, pH and temperature not specified in the publication
0.86
-
isozyme STPCA-2, pH not specified in the publication, temperature not specified in the publication
51.5
-
Co(II)-substituted enzyme, pH and temperature not specified in the publication
IC50 Value (47 results)
EC NUMBER
IC50 VALUE
IC50 VALUE MAXIMUM
COMMENTARY
LITERATURE
0.008
-
quinol oxidase activity of the membranes from the wild type shows a biphasic dependence on the cyanide concentration with the IC50 of 0.008 mM (relative amplitude, 21%) and 0.013 mM (79%), at 25°C in 50 mM potassium phosphate (pH 6.5)
13
-
quinol oxidase activity of the membranes from the wild type shows a biphasic dependence on the cyanide concentration with the IC50 of 0.008 mM (relative amplitude, 21%) and 13 mM (79%), at 25°C in 50 mM potassium phosphate (pH 6.5)
0.012
-
mutant enzyme W105F, at pH 7.0 and 37°C for catalase activity and at pH 6.0 and 25°C for peroxidase activity
0.04
-
mutant enzyme H106C, at pH 7.0 and 37°C for catalase activity and at pH 6.0 and 25°C for peroxidase activity
0.055
-
mutant enzyme R102L, at pH 7.0 and 37°C for catalase activity and at pH 6.0 and 25°C for peroxidase activity
0.065
-
mutant enzyme W105L, at pH 7.0 and 37°C for catalase activity and at pH 6.0 and 25°C for peroxidase activity
0.075
-
mutant enzyme R102C, at pH 7.0 and 37°C for catalase activity and at pH 6.0 and 25°C for peroxidase activity
0.09
-
wild type enzyme, at pH 7.0 and 37°C for catalase activity and at pH 6.0 and 25°C for peroxidase activity
0.21
-
mutant enzyme H106Y, at pH 7.0 and 37°C for catalase activity and at pH 6.0 and 25°C for peroxidase activity
0.39
-
mutant enzyme R102K, at pH 7.0 and 37°C for catalase activity and at pH 6.0 and 25°C for peroxidase activity
1
-
catalase activity, in 50 mM potassium phosphate/sodium citrate buffer, pH 4.5, at 80°C
1
-
peroxidase activity, in 50 mM potassium phosphate/sodium citrate buffer, pH 4.5, at 80°C
0.01
-
using 24-methylenecycloartanol as substrate, at 30°C, pH not specified in the publication
0.05
-
using 24-ethylidenelophenol as substrate, at 30°C, pH not specified in the publication
0.015
-
isozyme CAH8, in 20 mM 4-(2-hydroxyethyl)-1-piperazine propane sulfonic acid, pH 8.0, at 4°C
0.061
-
isozyme CAH7, in 20 mM 4-(2-hydroxyethyl)-1-piperazine propane sulfonic acid, pH 8.0, at 4°C