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Your query returned 24 entries. Printable version
EC | 4.2.1.139 | Relevance: 100% | ||||||||||
Accepted name: | pterocarpan synthase | |||||||||||
Reaction: | a (4R)-4,2′-dihydroxyisoflavan = a pterocarpan + H2O | |||||||||||
For diagram of medicarpin and formononetin derivatives biosynthesis, click here | ||||||||||||
Glossary: | an isoflavan = an isoflavonoid with a 3,4-dihydro-3-aryl-2H-1-benzopyran skeleton. (–)-medicarpin = (6aR,11aR)-9-methoxy-6a,11a-dihydro-6H-[1]benzofuro[3,2-c]chromen-3-ol (+)-medicarpin = (6aS,11aS)-9-methoxy-6a,11a-dihydro-6H-[1]benzofuro[3,2-c]chromen-3-ol (–)-maackiain = (6aR,12aR)-6a,12a-dihydro-6H-[1,3]dioxolo[5,6][1]benzofuro[3,2-c]chromen-3-ol (+)-maackiain = (6aS,12aS)-6a,12a-dihydro-6H-[1,3]dioxolo[5,6][1]benzofuro[3,2-c]chromen-3-ol (+)-pterocarpan = (6aR,11aR)-6a,11a-dihydro-6H-[1]benzofuran[3,2-c][1]benzopyran |
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Other name(s): | medicarpin synthase; medicarpan synthase; 7,2′-dihydroxy-4′-methoxyisoflavanol dehydratase; 2′,7-dihydroxy-4′-methoxyisoflavanol dehydratase; DMI dehydratase; DMID; 2′-hydroxyisoflavanol 4,2′-dehydratase; PTS (gene name); 4′-methoxyisoflavan-2′,4,7-triol hydro-lyase [(–)-medicarpin-forming] | |||||||||||
Systematic name: | (4R)-4,2′-dihydroxyisoflavan hydro-lyase (pterocarpan-forming) | |||||||||||
Comments: | The enzyme catalyses the formation of the additional ring in pterocarpan, the basic structure of phytoalexins produced by leguminous plants, including (–)-medicarpin, (+)-medicarpin, (–)-maackiain and (+)-maackiain. The enzyme requires that the hydroxyl group at C-4 of the substrate is in the (4R) configuration. The configuration of the hydrogen atom at C-3 determines whether the pterocarpan is the (+)- or (–)-enantiomer. The enzyme contains amino acid motifs characteristic of dirigent proteins. | |||||||||||
Links to other databases: | BRENDA, EXPASY, KEGG, MetaCyc, PDB | |||||||||||
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EC | 1.1.1.246 | |||||||||||
Transferred entry: | pterocarpin synthase. This activity is now known to be catalysed by two enzymes, vestitone reductase (EC 1.1.1.348) and medicarpin synthase (EC 4.2.1.139). | |||||||||||
EC | 1.14.13.52 | |||||||||||
Transferred entry: | isoflavone 3′-hydroxylase. Now EC 1.14.14.88, isoflavone 3′-hydroxylase | |||||||||||
EC | 1.1.1.348 | Relevance: 78.9% | ||||||||||
Accepted name: | (3R)-2′-hydroxyisoflavanone reductase | |||||||||||
Reaction: | a (4R)-4,2′-dihydroxyisoflavan + NADP+ = a (3R)-2′-hydroxyisoflavanone + NADPH + H+ | |||||||||||
For diagram of medicarpin and formononetin derivatives biosynthesis, click here | ||||||||||||
Glossary: | (3R)-vestitone = (3R)-2′,7-dihydroxy-4′-methoxyisoflavanone | |||||||||||
Other name(s): | vestitone reductase; pterocarpin synthase (incorrect); pterocarpan synthase (incorrect) | |||||||||||
Systematic name: | (3R)-2′-hydroxyisoflavanone:NADP+ 4-oxidoreductase | |||||||||||
Comments: | This plant enzyme participates in the biosynthesis of the pterocarpan phytoalexins medicarpin, maackiain, and several forms of glyceollin. The enzyme has a strict stereo specificity for the 3R-isoflavanones. | |||||||||||
Links to other databases: | BRENDA, EXPASY, KEGG, MetaCyc, PDB, CAS registry number: 118477-70-6 | |||||||||||
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EC | 1.14.13.53 | |||||||||||
Transferred entry: | 4′-methoxyisoflavone 2′-hydroxylase. Now EC 1.14.14.89, 4′-methoxyisoflavone 2′-hydroxylase | |||||||||||
EC | 1.14.14.88 | Relevance: 77.2% | ||||||||||
Accepted name: | isoflavone 3′-hydroxylase | |||||||||||
Reaction: | formononetin + [reduced NADPH—hemoprotein reductase] + O2 = calycosin + [oxidized NADPH—hemoprotein reductase] + H2O | |||||||||||
For diagram of medicarpin and formononetin derivatives biosynthesis, click here | ||||||||||||
Glossary: | calycosin = 3′-hydroxyformononetin | |||||||||||
Other name(s): | isoflavone 3′-monooxygenase; CYP81E9 | |||||||||||
Systematic name: | formononetin,[reduced NADPH—hemoprotein reductase]:oxygen oxidoreductase (3′-hydroxylating) | |||||||||||
Comments: | A cytochrome P-450 (heme-thiolate) protein. Also acts on biochanin A and other isoflavones with a 4′-methoxy group. Involved in the biosynthesis of the pterocarpin phytoalexins medicarpin and maackiain. | |||||||||||
Links to other databases: | BRENDA, EXPASY, KEGG, MetaCyc, CAS registry number: 110183-50-1 | |||||||||||
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EC | 1.14.13.89 | |||||||||||
Transferred entry: | isoflavone 2-hydroxylase. Now EC 1.14.14.90, isoflavone 2-hydroxylase | |||||||||||
EC | 5.3.3.11 | Relevance: 50.2% | ||||||||||
Accepted name: | isopiperitenone Δ-isomerase | |||||||||||
Reaction: | isopiperitenone = piperitenone | |||||||||||
For diagram of (–)-carvone, perillyl aldehyde and pulegone biosynthesis, click here | ||||||||||||
Systematic name: | isopiperitenone Δ8-Δ4-isomerase | |||||||||||
Comments: | Involved in the biosynthesis of menthol and related monoterpenes in peppermint (Mentha piperita) leaves. | |||||||||||
Links to other databases: | BRENDA, EXPASY, KEGG, MetaCyc, CAS registry number: 96595-07-2 | |||||||||||
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EC | 1.3.1.45 | Relevance: 49.3% | ||||||||||
Accepted name: | 2′-hydroxyisoflavone reductase | |||||||||||
Reaction: | vestitone + NADP+ = 2′-hydroxyformononetin + NADPH + H+ | |||||||||||
For diagram of the biosynthesis of formononetin and derivatives, click here | ||||||||||||
Other name(s): | NADPH:2′-hydroxyisoflavone oxidoreductase; isoflavone reductase; 2′,7-dihydroxy-4′,5′-methylenedioxyisoflavone reductase | |||||||||||
Systematic name: | vestitone:NADP+ oxidoreductase | |||||||||||
Comments: | In the reverse reaction, a 2′-hydroxyisoflavone is reduced to an isoflavanone; 2′-hydroxypseudobaptigenin also acts. Involved in the biosynthesis of the pterocarpin phytoalexins medicarpin and maackiain. | |||||||||||
Links to other databases: | BRENDA, EXPASY, KEGG, MetaCyc, PDB, CAS registry number: 128449-69-4 | |||||||||||
References: |
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EC | 1.1.1.243 | Relevance: 47% | ||||||||||
Accepted name: | carveol dehydrogenase | |||||||||||
Reaction: | (–)-trans-carveol + NADP+ = (–)-carvone + NADPH + H+ | |||||||||||
For diagram of (–)-carvone, perillyl aldehyde and pulegone biosynthesis, click here | ||||||||||||
Other name(s): | (–)-trans-carveol dehydrogenase | |||||||||||
Systematic name: | (–)-trans-carveol:NADP+ oxidoreductase | |||||||||||
Links to other databases: | BRENDA, EAWAG-BBD, EXPASY, KEGG, MetaCyc, CAS registry number: 122653-66-1 | |||||||||||
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EC | 5.5.1.28 | Relevance: 45% | ||||||||||
Accepted name: | (–)-kolavenyl diphosphate synthase | |||||||||||
Reaction: | geranylgeranyl diphosphate = (–)-kolavenyl diphosphate | |||||||||||
For diagram of (–)-kolavenyl diphosphate derived diterpenoids, click here | ||||||||||||
Glossary: | (–)-kolavenyl diphosphate = (2E)-5-[(1R,2S,4aS,8aS)-1,2,4a,5-tetramethyl-1,2,3,4,4a,7,8,8a-octahydronaphthalen-1-yl]-3-methylpent-2-en-1-yl diposphate | |||||||||||
Other name(s): | SdKPS; TwTPS14; TwTPS10/KPS; SdCPS2; clerodienyl diphosphate synthase; CLPP | |||||||||||
Systematic name: | (–)-kolavenyl diphosphate lyase (ring-opening) | |||||||||||
Comments: | Isolated from the hallucinogenic plant Salvia divinorum (seer’s sage) and the medicinal plant Tripterygium wilfordii (thunder god vine). | |||||||||||
Links to other databases: | BRENDA, EXPASY, KEGG, MetaCyc | |||||||||||
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EC | 4.2.3.186 | Relevance: 45% | ||||||||||
Accepted name: | ent-13-epi-manoyl oxide synthase | |||||||||||
Reaction: | ent-8α-hydroxylabd-13-en-15-yl diphosphate = ent-13-epi-manoyl oxide + diphosphate | |||||||||||
For diagram of (–)-kolavenyl diphosphate derived diterpenoids, click here | ||||||||||||
Glossary: | Ent-13-epi-manoyl oxide = (13R)-ent-8,13-epoxylabd-14-ene | |||||||||||
Other name(s): | SmKSL2; ent-LDPP synthase | |||||||||||
Systematic name: | ent-8α-hydroxylabd-13-en-15-yl-diphosphate diphosphate-lyase (cyclizing, ent-13-epi-manoyl-oxide-forming) | |||||||||||
Comments: | Isolated from the plant Salvia miltiorrhiza (red sage). | |||||||||||
Links to other databases: | BRENDA, EXPASY, KEGG, MetaCyc | |||||||||||
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EC | 4.2.3.95 | Relevance: 44.7% | ||||||||||
Accepted name: | (-)-α-cuprenene synthase | |||||||||||
Reaction: | (2E,6E)-farnesyl diphosphate = (-)-α-cuprenene + diphosphate | |||||||||||
For diagram of biosynthesis of bicyclic sesquiterpenoids derived from bisabolyl cation, click here and for diagram of trichodiene and (–)-α-cuprenene biosynthesis, click here | ||||||||||||
Other name(s): | Cop6 | |||||||||||
Systematic name: | (-)-α-cuprenene hydrolase [cyclizing, (-)-α-cuprenene-forming] | |||||||||||
Comments: | The enzyme from the fungus Coprinopsis cinerea produces (-)-α-cuprenene with high selectivity. | |||||||||||
Links to other databases: | BRENDA, EXPASY, KEGG, MetaCyc | |||||||||||
References: |
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EC | 4.2.3.6 | Relevance: 43.2% | ||||||||||
Accepted name: | trichodiene synthase | |||||||||||
Reaction: | (2E,6E)-farnesyl diphosphate = trichodiene + diphosphate | |||||||||||
For diagram of biosynthesis of bicyclic sesquiterpenoids derived from bisabolyl cation, click here and for diagram of trichodiene and (–)-α-cuprenene biosynthesis, click here | ||||||||||||
Other name(s): | trichodiene synthetase; sesquiterpene cyclase; trans,trans-farnesyl-diphosphate sesquiterpenoid-lyase | |||||||||||
Systematic name: | (2E,6E)-farnesyl-diphosphate diphosphate-lyase (cyclizing, trichodiene-forming) | |||||||||||
Links to other databases: | BRENDA, EXPASY, KEGG, MetaCyc, PDB, CAS registry number: 101915-76-8 | |||||||||||
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EC | 1.14.13.104 | |||||||||||
Transferred entry: | (+)-menthofuran synthase. Now EC 1.14.14.143, (+)-menthofuran synthase | |||||||||||
EC | 1.3.99.25 | Relevance: 42.7% | ||||||||||
Accepted name: | carvone reductase | |||||||||||
Reaction: | (1) (+)-dihydrocarvone + acceptor = (–)-carvone + reduced acceptor (2) (–)-isodihydrocarvone + acceptor = (+)-carvone + reduced acceptor |
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For diagram of (–)-carvone catabolism, click here | ||||||||||||
Glossary: | (+)-dihydrocarvone = (1S,4R)-menth-8-en-2-one (+)-isodihydrocarvone = (1S,4R)-menth-8-en-2-one (–)-carvone = (4R)-mentha-1(6),8-dien-6-one = (5R)-2-methyl-5-(prop-1-en-2-yl)cyclohex-2-en-1-one |
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Systematic name: | (+)-dihydrocarvone:acceptor 1,6-oxidoreductase | |||||||||||
Comments: | This enzyme participates in the carveol and dihydrocarveol degradation pathway of the Gram-positive bacterium Rhodococcus erythropolis DCL14. The enzyme has not been purified, and requires an unknown cofactor, which is different from NAD+, NADP+ or a flavin. | |||||||||||
Links to other databases: | BRENDA, EXPASY, KEGG, MetaCyc | |||||||||||
References: |
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EC | 1.1.1.296 | Relevance: 42.4% | ||||||||||
Accepted name: | dihydrocarveol dehydrogenase | |||||||||||
Reaction: | menth-8-en-2-ol + NAD+ = menth-8-en-2-one + NADH + H+ | |||||||||||
For diagram of (–)-carvone catabolism, click here | ||||||||||||
Glossary: | (+)-dihydrocarveol = (1S,2S,4S)-menth-8-en-2-ol (+)-isodihydrocarveol = (1S,2S,4R)-menth-8-en-2-ol (+)-neoisodihydrocarveol = (1S,2R,4R)-menth-8-en-2-ol (–)-dihydrocarvone = (1S,4S)-menth-8-en-2-one (+)-isodihydrocarvone = (1S,4R)-menth-8-en-2-one |
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Other name(s): | carveol dehydrogenase (ambiguous) | |||||||||||
Systematic name: | menth-8-en-2-ol:NAD+ oxidoreductase | |||||||||||
Comments: | This enzyme from the Gram-positive bacterium Rhodococcus erythropolis DCL14 forms part of the carveol and dihydrocarveol degradation pathway. The enzyme accepts all eight stereoisomers of menth-8-en-2-ol as substrate, although some isomers are converted faster than others. The preferred substrates are (+)-neoisodihydrocarveol, (+)-isodihydrocarveol, (+)-dihydrocarveol and (–)-isodihydrocarveol. | |||||||||||
Links to other databases: | BRENDA, EXPASY, KEGG, MetaCyc | |||||||||||
References: |
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EC | 1.14.14.89 | Relevance: 41.7% | ||||||||||
Accepted name: | 4′-methoxyisoflavone 2′-hydroxylase | |||||||||||
Reaction: | formononetin + [reduced NADPH—hemoprotein reductase] + O2 = 2′-hydroxyformononetin + [oxidized NADPH—hemoprotein reductase] + H2O | |||||||||||
For diagram of the biosynthesis of formononetin and derivatives, click here | ||||||||||||
Other name(s): | CYP81E1 (gene name); CYP81E3 (gene name); CYP81E7 (gene name); isoflavone 2′-monooxygenase (ambiguous); isoflavone 2′-hydroxylase (ambiguous) | |||||||||||
Systematic name: | formononetin,[reduced NADPH—hemoprotein reductase]:oxygen oxidoreductase (2′-hydroxylating) | |||||||||||
Comments: | A cytochrome P-450 (heme-thiolate) protein. Acts on isoflavones with a 4′-methoxy group, such as formononetin and biochanin A. Involved in the biosynthesis of the pterocarpin phytoalexins medicarpin and maackiain. EC 1.14.14.90, isoflavone 2′-hydroxylase, is less specific and acts on other isoflavones as well as 4′-methoxyisoflavones. | |||||||||||
Links to other databases: | BRENDA, EXPASY, KEGG, MetaCyc, CAS registry number: 110183-49-8 | |||||||||||
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EC | 1.23.1.3 | Relevance: 41% | ||||||||||
Accepted name: | (–)-pinoresinol reductase | |||||||||||
Reaction: | (–)-lariciresinol + NADP+ = (–)-pinoresinol + NADPH + H+ | |||||||||||
For diagram of (–)-lariciresinol biosynthesis, click here | ||||||||||||
Glossary: | (–)-lariciresinol = 4-[(2R,3S,4S)-4-[(4-hydroxy-3-methoxyphenyl)methyl]-3-(hydroxymethyl)oxolan-2-yl]-2-methoxyphenol (–)-pinoresinol = (1R,3aS,4R,6aS)-4,4′-(tetrahydro-1H,3H-furo[3,4-c]furan-1,4-diyl)bis(2-methoxyphenol) |
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Other name(s): | pinoresinol/lariciresinol reductase; pinoresinol-lariciresinol reductases; (–)-pinoresinol-(–)-lariciresinol reductase; PLR | |||||||||||
Systematic name: | (–)-lariciresinol:NADP+ oxidoreductase | |||||||||||
Comments: | The reaction is catalysed in vivo in the opposite direction to that shown. A multifunctional enzyme that usually further reduces the product to (+)-secoisolariciresinol [EC 1.23.1.4, (–)-lariciresinol reductase]. Isolated from the plants Thuja plicata (western red cedar) [1], Linum perenne (perennial flax) [2] and Arabidopsis thaliana (thale cress) [3]. | |||||||||||
Links to other databases: | BRENDA, EXPASY, KEGG, MetaCyc, PDB | |||||||||||
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EC | 1.14.13.47 | |||||||||||
Transferred entry: | (S)-limonene 3-monooxygenase. Now EC 1.14.14.99, (S)-limonene 3-monooxygenase | |||||||||||
EC | 3.1.1.83 | Relevance: 40.1% | ||||||||||
Accepted name: | monoterpene ε-lactone hydrolase | |||||||||||
Reaction: | (1) isoprop(en)ylmethyloxepan-2-one + H2O = 6-hydroxyisoprop(en)ylmethylhexanoate (general reaction) (2) 4-isopropenyl-7-methyloxepan-2-one + H2O = 6-hydroxy-3-isopropenylheptanoate (3) 7-isopropyl-4-methyloxepan-2-one + H2O = 6-hydroxy-3,7-dimethyloctanoate |
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For diagram of (–)-carvone catabolism, click here and for diagram of menthol biosynthesis, click here | ||||||||||||
Other name(s): | MLH | |||||||||||
Systematic name: | isoprop(en)ylmethyloxepan-2-one lactonohydrolase | |||||||||||
Comments: | The enzyme catalyses the ring opening of ε-lactones which are formed during degradation of dihydrocarveol by the Gram-positive bacterium Rhodococcus erythropolis DCL14. The enzyme also acts on ethyl caproate, indicating that it is an esterase with a preference for lactones (internal cyclic esters). The enzyme is not stereoselective. | |||||||||||
Links to other databases: | BRENDA, EXPASY, KEGG, MetaCyc | |||||||||||
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EC | 1.14.13.48 | |||||||||||
Transferred entry: | (S)-limonene 6-monooxygenase. Now classified as EC 1.14.14.51, (S)-limonene 6-monooxygenase | |||||||||||
EC | 1.14.13.49 | |||||||||||
Transferred entry: | (S)-limonene 7-monooxygenase. Now classified as EC 1.14.14.52, (S)-limonene 7-monooxygenase | |||||||||||
EC | 1.14.13.105 | Relevance: 33.9% | ||||||||||
Accepted name: | monocyclic monoterpene ketone monooxygenase | |||||||||||
Reaction: | (1) (–)-menthone + NADPH + H+ + O2 = (4R,7S)-7-isopropyl-4-methyloxepan-2-one + NADP+ + H2O (2) dihydrocarvone + NADPH + H+ + O2 = 4-isopropenyl-7-methyloxepan-2-one + NADP+ + H2O (3) (iso)-dihydrocarvone + NADPH + H+ + O2 = 6-isopropenyl-3-methyloxepan-2-one + NADP+ + H2O (4a) 1-hydroxymenth-8-en-2-one + NADPH + H+ + O2 = 7-hydroxy-4-isopropenyl-7-methyloxepan-2-one + NADP+ + H2O (4b) 7-hydroxy-4-isopropenyl-7-methyloxepan-2-one = 3-isopropenyl-6-oxoheptanoate (spontaneous) |
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For diagram of (–)-carvone catabolism, click here, for diagram of limonene catabolism, click here and for diagram of menthol biosynthesis, click here | ||||||||||||
Other name(s): | 1-hydroxy-2-oxolimonene 1,2-monooxygenase; dihydrocarvone 1,2-monooxygenase; MMKMO | |||||||||||
Systematic name: | (–)-menthone,NADPH:oxygen oxidoreductase | |||||||||||
Comments: | A flavoprotein (FAD). This Baeyer-Villiger monooxygenase enzyme from the Gram-positive bacterium Rhodococcus erythropolis DCL14 has wide substrate specificity, catalysing the lactonization of a large number of monocyclic monoterpene ketones and substituted cyclohexanones [2]. Both (1R,4S)- and (1S,4R)-1-hydroxymenth-8-en-2-one are metabolized, with the lactone product spontaneously rearranging to form 3-isopropenyl-6-oxoheptanoate [1]. | |||||||||||
Links to other databases: | BRENDA, EXPASY, KEGG, MetaCyc | |||||||||||
References: |
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