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Your query returned 34 entries. Printable version
EC | 1.14.13.47 | |||||||||||||||||||||||||||||
Transferred entry: | (S)-limonene 3-monooxygenase. Now EC 1.14.14.99, (S)-limonene 3-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 | 1.14.13.48 | |||||||||||||||||||||||||||||
Transferred entry: | (S)-limonene 6-monooxygenase. Now classified as EC 1.14.14.51, (S)-limonene 6-monooxygenase | |||||||||||||||||||||||||||||
EC | 1.14.13.107 | Relevance: 92.1% | ||||||||||||||||||||||||||||
Accepted name: | limonene 1,2-monooxygenase | |||||||||||||||||||||||||||||
Reaction: | (1) (S)-limonene + NAD(P)H + H+ + O2 = 1,2-epoxymenth-8-ene + NAD(P)+ + H2O (2) (R)-limonene + NAD(P)H + H+ + O2 = 1,2-epoxymenth-8-ene + NAD(P)+ + H2O |
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For diagram of limonene catabolism, click here | ||||||||||||||||||||||||||||||
Glossary: | limonene = a monoterpenoid (S)-limonene = (-)-limonene (R)-limonene = (+)-limonene limonene-1,2-epoxide = 1,2-epoxymenth-8-ene = 1-methyl-4-(prop-1-en-2-yl)-7-oxabicyclo[4.1.0]heptane |
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Systematic name: | limonene,NAD(P)H:oxygen oxidoreductase | |||||||||||||||||||||||||||||
Comments: | A flavoprotein (FAD). Limonene is the most widespread terpene and is formed by more than 300 plants. Rhodococcus erythropolis DCL14, a Gram-positive bacterium, is able to grow on both (S)-limonene and (R)-limonene as the sole source of carbon and energy. NADPH can act instead of NADH, although more slowly. It has not been established if the product formed is optically pure or a mixture of two enantiomers. | |||||||||||||||||||||||||||||
Links to other databases: | BRENDA, EAWAG-BBD, EXPASY, KEGG, MetaCyc, PDB | |||||||||||||||||||||||||||||
References: |
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EC | 1.14.13.80 | |||||||||||||||||||||||||||||
Transferred entry: | (R)-limonene 6-monooxygenase. Now classified as EC 1.14.14.53, (R)-limonene 6-monooxygenase | |||||||||||||||||||||||||||||
EC | 1.14.14.99 | Relevance: 78.4% | ||||||||||||||||||||||||||||
Accepted name: | (S)-limonene 3-monooxygenase | |||||||||||||||||||||||||||||
Reaction: | (S)-limonene + [reduced NADPH—hemoprotein reductase] + O2 = (–)-trans-isopiperitenol + [oxidized NADPH—hemoprotein reductase] + H2O | |||||||||||||||||||||||||||||
For diagram of perillyl alcohol, isopiperitol and carveol biosynthesis, click here | ||||||||||||||||||||||||||||||
Glossary: | limonene = a monoterpenoid (S)-limonene = (–)-limonene |
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Other name(s): | (–)-limonene 3-hydroxylase; (–)-limonene 3-monooxygenase; CYP71D15 (gene name) | |||||||||||||||||||||||||||||
Systematic name: | (S)-limonene,[reduced NADPH—hemoprotein reductase]:oxygen oxidoreductase (3-hydroxylating) | |||||||||||||||||||||||||||||
Comments: | A cytochrome P-450 (heme-thiolate) protein from peppermint (Mentha piperita). | |||||||||||||||||||||||||||||
Links to other databases: | BRENDA, EAWAG-BBD, EXPASY, KEGG, MetaCyc, CAS registry number: 138066-92-9 | |||||||||||||||||||||||||||||
References: |
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EC | 1.14.14.53 | Relevance: 77.7% | ||||||||||||||||||||||||||||
Accepted name: | (R)-limonene 6-monooxygenase | |||||||||||||||||||||||||||||
Reaction: | (R)-limonene + [reduced NADPH—hemoprotein reductase] + O2 = (+)-trans-carveol + [oxidized NADPH—hemoprotein reductase] + H2O | |||||||||||||||||||||||||||||
For diagram of carvone biosynthesis, click here | ||||||||||||||||||||||||||||||
Glossary: | limonene = a monoterpenoid (R)-limonene = (+)-limonene |
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Other name(s): | (+)-limonene-6-hydroxylase; (+)-limonene 6-monooxygenase | |||||||||||||||||||||||||||||
Systematic name: | (R)-limonene,[reduced NADPH—hemoprotein reductase]:oxygen oxidoreductase (6-hydroxylating) | |||||||||||||||||||||||||||||
Comments: | The reaction is stereospecific with over 95% yield of (+)-trans-carveol from (R)-limonene. (S)-Limonene, the substrate for EC 1.14.14.51, (S)-limonene 6-monooxygenase, is not a substrate. Forms part of the carvone biosynthesis pathway in Carum carvi (caraway) seeds. | |||||||||||||||||||||||||||||
Links to other databases: | BRENDA, EXPASY, KEGG, MetaCyc, PDB, CAS registry number: 221461-49-0 | |||||||||||||||||||||||||||||
References: |
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EC | 4.2.3.16 | Relevance: 76.2% | ||||||||||||||||||||||||||||
Accepted name: | (4S)-limonene synthase | |||||||||||||||||||||||||||||
Reaction: | geranyl diphosphate = (S)-limonene + diphosphate | |||||||||||||||||||||||||||||
For diagram of perillyl alcohol, isopiperitol and carveol biosynthesis, click here | ||||||||||||||||||||||||||||||
Glossary: | limonene = a monoterpenoid (S)-limonene = (-)-limonene |
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Other name(s): | (-)-(4S)-limonene synthase; 4S-(-)-limonene synthase; geranyldiphosphate diphosphate lyase (limonene forming); geranyldiphosphate diphosphate lyase [cyclizing, (4S)-limonene-forming]; geranyl-diphosphate diphosphate-lyase [cyclizing; (-)-(4S)-limonene-forming] | |||||||||||||||||||||||||||||
Systematic name: | geranyl-diphosphate diphosphate-lyase [cyclizing; (S)-limonene-forming] | |||||||||||||||||||||||||||||
Comments: | A recombinant enzyme (also known as a monoterpene synthase or cyclase) from the grand fir (Abies grandis) requires Mn2+ and K+ for activity. Mg2+ is essentially ineffective as the divalent metal ion cofactor. | |||||||||||||||||||||||||||||
Links to other databases: | BRENDA, EXPASY, KEGG, MetaCyc, CAS registry number: 110639-20-8 | |||||||||||||||||||||||||||||
References: |
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EC | 1.14.14.51 | Relevance: 72.5% | ||||||||||||||||||||||||||||
Accepted name: | (S)-limonene 6-monooxygenase | |||||||||||||||||||||||||||||
Reaction: | (S)-limonene + [reduced NADPH—hemoprotein reductase] + O2 = (–)-trans-carveol + [oxidized NADPH—hemoprotein reductase] + H2O | |||||||||||||||||||||||||||||
For diagram of perillyl alcohol, isopiperitol and carveol biosynthesis, click here | ||||||||||||||||||||||||||||||
Glossary: | limonene = a monoterpenoid (S)-limonene = (–)-limonene |
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Other name(s): | (–)-limonene 6-hydroxylase; (–)-limonene 6-monooxygenase; (–)-limonene,NADPH:oxygen oxidoreductase (6-hydroxylating) | |||||||||||||||||||||||||||||
Systematic name: | (S)-limonene,[reduced NADPH—hemoprotein reductase]:oxygen oxidoreductase (6-hydroxylating) | |||||||||||||||||||||||||||||
Comments: | A cytochrome P-450 (heme thiolate) enzyme. The enzyme participates in the biosynthesis of (–)-carvone, which is responsible for the aroma of spearmint. | |||||||||||||||||||||||||||||
Links to other databases: | BRENDA, EAWAG-BBD, EXPASY, KEGG, MetaCyc, PDB, CAS registry number: 138066-93-0 | |||||||||||||||||||||||||||||
References: |
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EC | 4.2.3.20 | Relevance: 70.2% | ||||||||||||||||||||||||||||
Accepted name: | (R)-limonene synthase | |||||||||||||||||||||||||||||
Reaction: | geranyl diphosphate = (R)-limonene + diphosphate | |||||||||||||||||||||||||||||
For diagram of carvone biosynthesis, click here | ||||||||||||||||||||||||||||||
Glossary: | (R)-limonene = (+)-limonene | |||||||||||||||||||||||||||||
Other name(s): | (+)-limonene synthase; geranyldiphosphate diphosphate lyase [(+)-(R)-limonene-forming]; geranyl-diphosphate diphosphate-lyase [cyclizing, (+)-(4R)-limonene-forming] | |||||||||||||||||||||||||||||
Systematic name: | geranyl-diphosphate diphosphate-lyase [cyclizing, (R)-limonene-forming] | |||||||||||||||||||||||||||||
Comments: | Forms the first step of carvone biosynthesis in caraway. The enzyme from Carum carvi (caraway) seeds requires a divalent metal ion (preferably Mn2+) for catalysis. This enzyme occurs in Citrus, Carum (caraway) and Anethum (dill); (-)-limonene, however, is made in the fir, Abies, and mint, Mentha, by EC 4.2.3.16, (4S)-limonene synthase. | |||||||||||||||||||||||||||||
Links to other databases: | BRENDA, EXPASY, KEGG, MetaCyc, PDB, CAS registry number: 155807-65-1 | |||||||||||||||||||||||||||||
References: |
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EC | 1.14.14.52 | Relevance: 68.7% | ||||||||||||||||||||||||||||
Accepted name: | (S)-limonene 7-monooxygenase | |||||||||||||||||||||||||||||
Reaction: | (S)-limonene + [reduced NADPH—hemoprotein reductase] + O2 = (–)-perillyl alcohol + [oxidized NADPH—hemoprotein reductase] + H2O | |||||||||||||||||||||||||||||
For diagram of perillyl alcohol, isopiperitol and carveol biosynthesis, click here | ||||||||||||||||||||||||||||||
Glossary: | limonene = a monoterpenoid (S)-limonene = (–)-limonene |
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Other name(s): | (–)-limonene 7-monooxygenase; (–)-limonene hydroxylase; (–)-limonene monooxygenase; (–)-limonene,NADPH:oxygen oxidoreductase (7-hydroxylating) | |||||||||||||||||||||||||||||
Systematic name: | (S)-limonene,[reduced NADPH—hemoprotein reductase]:oxygen oxidoreductase (7-hydroxylating) | |||||||||||||||||||||||||||||
Comments: | A cytochrome P-450 (heme thiolate) enzyme. The enzyme, characterized from the plant Perilla frutescens, participates in the biosynthesis of perillyl aldehyde, the major constituent of the essential oil that accumulates in the glandular trichomes of this plant. Some forms of the enzyme also catalyse the oxidation of (–)-perillyl alcohol to (–)-perillyl aldehyde. | |||||||||||||||||||||||||||||
Links to other databases: | BRENDA, EAWAG-BBD, EXPASY, KEGG, MetaCyc, PDB, CAS registry number: 122653-75-2 | |||||||||||||||||||||||||||||
References: |
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EC | 1.17.99.8 | Relevance: 65.6% | ||||||||||||||||||||||||||||
Accepted name: | limonene dehydrogenase | |||||||||||||||||||||||||||||
Reaction: | (1) (S)-limonene + H2O + acceptor = (–)-perillyl alcohol + reduced acceptor (2) (R)-limonene + H2O + acceptor = (+)-perillyl alcohol + reduced acceptor |
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Glossary: | limonene = 1-methyl-4-(prop-1-en-2-yl)cyclohex-1-ene perillyl alcohol = [4-(prop-1-en-2-yl)cyclohex-1-en-1-yl]methanol (–)-perillyl alcohol = (S)-perillyl alcohol = [(4S)-4-(prop-1-en-2-yl)cyclohex-1-en-1-yl]methanol (+)-perillyl alcohol = (R)-perillyl alcohol = [(4R)-4-(prop-1-en-2-yl)cyclohex-1-en-1-yl]methanol (–)-limonene = (S)-limonene = (4S)-1-methyl-4-(prop-1-en-2-yl)cyclohexene (+)-limonene = (R)-limonene = (4R)-1-methyl-4-(prop-1-en-2-yl)cyclohexene |
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Other name(s): | ctmAB (gene names) | |||||||||||||||||||||||||||||
Systematic name: | limonene:acceptor oxidoreductase (7-hydroxylating) | |||||||||||||||||||||||||||||
Comments: | Contains FAD. The enzyme, characterized from the bacterium Castellaniella defragrans 65Phen, hydroxylates the R- and S-enantiomers at a similar rate. The in vivo electron acceptor may be a heterodimeric electron transfer flavoprotein (ETF). | |||||||||||||||||||||||||||||
Links to other databases: | BRENDA, EXPASY, KEGG, MetaCyc | |||||||||||||||||||||||||||||
References: |
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EC | 3.3.2.8 | Relevance: 62.1% | ||||||||||||||||||||||||||||
Accepted name: | limonene-1,2-epoxide hydrolase | |||||||||||||||||||||||||||||
Reaction: | 1,2-epoxymenth-8-ene + H2O = menth-8-ene-1,2-diol | |||||||||||||||||||||||||||||
For diagram of limonene catabolism, click here | ||||||||||||||||||||||||||||||
Glossary: | limonene = a monoterpenoid limonene-1,2-epoxide = 1,2-epoxymenth-8-ene limonene-1,2-diol = menth-8-ene-1,2-diol |
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Other name(s): | limonene oxide hydrolase | |||||||||||||||||||||||||||||
Systematic name: | 1,2-epoxymenth-8-ene hydrolase | |||||||||||||||||||||||||||||
Comments: | Involved in the monoterpene degradation pathway of the actinomycete Rhodococcus erythropolis. The enzyme hydrolyses several alicyclic and 1-methyl-substituted epoxides, such as 1-methylcyclohexene oxide, indene oxide and cyclohexene oxide. It differs from the previously described epoxide hydrolases [EC 3.3.2.4 (trans-epoxysuccinate hydrolase), EC 3.3.2.6 (leukotriene-A4 hydrolase), EC 3.3.2.7 (hepoxilin-epoxide hydrolase), EC 3.3.2.9 (microsomal epoxide hydrolase) and EC 3.3.2.10 (soluble epoxide hydrolase)] as it is not inhibited by 2-bromo-4′-nitroacetophenone, diethyl dicarbonate, 4-fluorochalcone oxide or 1,10-phenanthroline. Both enantiomers of menth-8-ene-1,2-diol [i.e. (1R,2R,4S)-menth-8-ene-1,2-diol and (1S,2S,4R)-menth-8-ene-1,2-diol] are metabolized. | |||||||||||||||||||||||||||||
Links to other databases: | BRENDA, EAWAG-BBD, EXPASY, KEGG, MetaCyc, PDB, CAS registry number: 216503-88-7 | |||||||||||||||||||||||||||||
References: |
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EC | 1.1.1.297 | Relevance: 56.1% | ||||||||||||||||||||||||||||
Accepted name: | limonene-1,2-diol dehydrogenase | |||||||||||||||||||||||||||||
Reaction: | menth-8-ene-1,2-diol + NAD+ = 1-hydroxymenth-8-en-2-one + NADH + H+ (general reaction) (1) (1S,2S,4R)-menth-8-ene-1,2-diol + NAD+ = (1S,4R)-1-hydroxymenth-8-en-2-one + NADH + H+ (2) (1R,2R,4S)-menth-8-ene-1,2-diol + NAD+ = (1R,4S)-1-hydroxymenth-8-en-2-one + NADH + H+ |
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For diagram of limonene catabolism, click here | ||||||||||||||||||||||||||||||
Glossary: | limonene-1,2-diol = menth-8-ene-1,2-diol = 1-methyl-4-(prop-1-en-2-yl)cyclohexane-1,2-diol | |||||||||||||||||||||||||||||
Other name(s): | NAD+-dependent limonene-1,2-diol dehydrogenase | |||||||||||||||||||||||||||||
Systematic name: | menth-8-ene-1,2-diol:NAD+ oxidoreductase | |||||||||||||||||||||||||||||
Comments: | While the enzyme from the Gram-positive bacterium Rhodococcus erythropolis DCL14 can use both (1S,2S,4R)- and (1R,2R,4S)-menth-8-ene-1,2-diol as substrate, activity is higher with (1S,2S,4R)-menth-8-ene-1,2-diol as substrate. | |||||||||||||||||||||||||||||
Links to other databases: | BRENDA, EXPASY, KEGG, MetaCyc | |||||||||||||||||||||||||||||
References: |
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EC | 1.14.13.104 | |||||||||||||||||||||||||||||
Transferred entry: | (+)-menthofuran synthase. Now EC 1.14.14.143, (+)-menthofuran synthase | |||||||||||||||||||||||||||||
EC | 4.2.3.112 | Relevance: 43.5% | ||||||||||||||||||||||||||||
Accepted name: | (+)-α-terpineol synthase | |||||||||||||||||||||||||||||
Reaction: | geranyl diphosphate + H2O = (+)-α-terpineol + diphosphate | |||||||||||||||||||||||||||||
For diagram of menthane monoterpenoid biosynthesis, click here | ||||||||||||||||||||||||||||||
Systematic name: | geranyl-diphosphate diphosphate-lyase [cyclizing, (+)-α-terpineol-forming] | |||||||||||||||||||||||||||||
Comments: | The enzyme has been characterized from Santalum album (sandalwood). Also forms some (-)-limonene and traces of other monoterpenoids. See EC 4.2.3.16 (4S)-limonene synthase. | |||||||||||||||||||||||||||||
Links to other databases: | BRENDA, EXPASY, KEGG, MetaCyc | |||||||||||||||||||||||||||||
References: |
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EC | 4.2.3.105 | Relevance: 41.8% | ||||||||||||||||||||||||||||
Accepted name: | tricyclene synthase | |||||||||||||||||||||||||||||
Reaction: | geranyl diphosphate = tricyclene + diphosphate | |||||||||||||||||||||||||||||
For diagram of bornane and related monoterpenoids, click here | ||||||||||||||||||||||||||||||
Other name(s): | TPS3 | |||||||||||||||||||||||||||||
Systematic name: | geranyl-diphosphate diphosphate-lyase (cyclizing; tricyclene-forming) | |||||||||||||||||||||||||||||
Comments: | The enzyme from Solanum lycopersicum (tomato) gives a mixture of tricyclene, camphene, β-myrcene, limonene, and traces of several other monoterpenoids. See EC 4.2.3.117. (-)-camphene synthase, EC 4.2.3.15, myrcene synthase and EC 4.2.3.16, (4S)-limonene synthase. | |||||||||||||||||||||||||||||
Links to other databases: | BRENDA, EXPASY, KEGG, MetaCyc | |||||||||||||||||||||||||||||
References: |
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EC | 1.14.13.105 | Relevance: 40% | ||||||||||||||||||||||||||||
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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EC | 4.2.3.38 | Relevance: 38.3% | ||||||||||||||||||||||||||||
Accepted name: | α-bisabolene synthase | |||||||||||||||||||||||||||||
Reaction: | (2E,6E)-farnesyl diphosphate = (E)-α-bisabolene + diphosphate | |||||||||||||||||||||||||||||
For diagram of bisabolene-derived sesquiterpenoid biosynthesis, click here | ||||||||||||||||||||||||||||||
Other name(s): | bisabolene synthase | |||||||||||||||||||||||||||||
Systematic name: | (2E,6E)-farnesyl-diphosphate diphosphate-lyase [(E)-α-bisabolene-forming] | |||||||||||||||||||||||||||||
Comments: | This cytosolic sesquiterpenoid synthase requires a divalent cation cofactor (Mg2+ or, to a lesser extent, Mn2+) to neutralize the negative charge of the diphosphate leaving group. While unlikely to encounter geranyl diphosphate (GDP) in vivo as it is localized to plastids, the enzyme can use GDP as a substrate in vitro to produce (+)-(4R)-limonene [cf. EC 4.2.3.20, (R)-limonene synthase]. The enzyme is induced as part of a defense mechanism in the grand fir Abies grandis as a response to stem wounding. | |||||||||||||||||||||||||||||
Links to other databases: | BRENDA, EXPASY, KEGG, MetaCyc, PDB | |||||||||||||||||||||||||||||
References: |
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EC | 4.2.3.117 | Relevance: 37.9% | ||||||||||||||||||||||||||||
Accepted name: | (-)-camphene synthase | |||||||||||||||||||||||||||||
Reaction: | geranyl diphosphate = (-)-camphene + diphosphate | |||||||||||||||||||||||||||||
Glossary: | (-)-camphene = (1S,4R)-2,2-dimethyl-3-methylenebicyclo[2.2.1]heptane | |||||||||||||||||||||||||||||
Other name(s): | CS | |||||||||||||||||||||||||||||
Systematic name: | geranyl-diphosphate diphosphate-lyase [cyclizing, (-)-camphene-forming] | |||||||||||||||||||||||||||||
Comments: | (-)-Camphene is the major product in Abies grandis (grand fir) with traces of other monoterpenoids [1]. In Pseudotsuga menziesii (Douglas-fir) there are about equal parts of (-)-camphene and (-)-α-pinene with traces of four other monoterpenoids [2,3]. In Solanum lycopersicum (tomato) tricyclene, β-myrcene, limonene, and traces of several other monoterpenoids are also formed [4]. See also EC 4.2.3.15 myrcene synthase, EC 4.2.3.16 (4S)-limonene synthase, EC 4.2.3.119 (-)-α-pinene synthase and EC 4.2.3.105 tricyclene synthase. | |||||||||||||||||||||||||||||
Links to other databases: | BRENDA, EXPASY, KEGG, MetaCyc | |||||||||||||||||||||||||||||
References: |
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EC | 5.3.3.11 | Relevance: 30.7% | ||||||||||||||||||||||||||||
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 | |||||||||||||||||||||||||||||
References: |
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EC | 4.2.3.119 | Relevance: 29.3% | ||||||||||||||||||||||||||||
Accepted name: | (-)-α-pinene synthase | |||||||||||||||||||||||||||||
Reaction: | geranyl diphosphate = (-)-α-pinene + diphosphate | |||||||||||||||||||||||||||||
For diagram of pinene and related monoterpenoids, click here | ||||||||||||||||||||||||||||||
Glossary: | (-)-α-pinene = (1S,5S)-2,6,6-trimethylbicyclo[3.1.1]hept-2-ene | |||||||||||||||||||||||||||||
Other name(s): | (-)-α-pinene/(-)-camphene synthase; (-)-α-pinene cyclase | |||||||||||||||||||||||||||||
Systematic name: | geranyl-diphosphate diphosphate-lyase [cyclizing, (-)-α-pinene-forming] | |||||||||||||||||||||||||||||
Comments: | Cyclase II of Salvia officinalis (sage) gives about equal parts (-)-α-pinene, (-)-β-pinene and (-)-camphene, plus traces of other monoterpenoids. (3S)-Linalyl diphosphate can also be used by the enzyme in preference to (3R)-linalyl diphosphate. The 4-pro-S-hydrogen of geranyl diphosphate is lost. Requires Mg2+ (preferred to Mn2+) [1-6]. The enzyme from Abies grandis (grand fir) gives roughly equal parts (-)-α-pinene and (-)-β-pinene. However the clone ag11 gave 35% (-)-limonene, 24% (-)-α-pinene and 20% (-)-β-phellandrene. It requires Mn2+ and K+ (Mg2+ is ineffective) [7-10]. Synthase I from Pinus taeda (loblolly pine) produces (-)-α-pinene with traces of (-)-β-pinene and requires Mn2+ (preferred to Mg2+) [11,12]. The enzyme from Picea sitchensis (Sika spruce) forms 70% (-)-α-pinene and 30% (-)-β-pinene [13]. The recombinant PmeTPS1 enzyme from Pseudotsuga menziesii (Douglas fir) gave roughly equal proportions of (-)-α-pinene and (-)-camphene plus traces of other monoterpenoids [14]. See also EC 4.2.3.120, (-)-β-pinene synthase; EC 4.2.3.117, (-)-camphene synthase; EC 4.2.3.16, (-)-limonene synthase; and EC 4.2.3.52, (-)-β-phellandrene synthase. | |||||||||||||||||||||||||||||
Links to other databases: | BRENDA, EXPASY, KEGG, MetaCyc | |||||||||||||||||||||||||||||
References: |
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EC | 1.1.1.243 | Relevance: 28.8% | ||||||||||||||||||||||||||||
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 | |||||||||||||||||||||||||||||
References: |
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EC | 5.5.1.28 | Relevance: 27.6% | ||||||||||||||||||||||||||||
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 | |||||||||||||||||||||||||||||
References: |
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EC | 4.2.3.186 | Relevance: 27.6% | ||||||||||||||||||||||||||||
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 | |||||||||||||||||||||||||||||
References: |
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EC | 4.2.3.95 | Relevance: 27.4% | ||||||||||||||||||||||||||||
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: 26.5% | ||||||||||||||||||||||||||||
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 | |||||||||||||||||||||||||||||
References: |
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EC | 1.3.99.25 | Relevance: 26.2% | ||||||||||||||||||||||||||||
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: 26% | ||||||||||||||||||||||||||||
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 | 1.23.1.3 | Relevance: 25.1% | ||||||||||||||||||||||||||||
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 | |||||||||||||||||||||||||||||
References: |
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EC | 3.1.1.83 | Relevance: 24.6% | ||||||||||||||||||||||||||||
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 | |||||||||||||||||||||||||||||
References: |
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EC | 1.14.13.207 | |||||||||||||||||||||||||||||
Transferred entry: | ipsdienol synthase. Now EC 1.14.14.31, ipsdienol synthase | |||||||||||||||||||||||||||||
EC | 1.14.14.31 | Relevance: 22% | ||||||||||||||||||||||||||||
Accepted name: | ipsdienol synthase | |||||||||||||||||||||||||||||
Reaction: | myrcene + [reduced NADPH—hemoprotein reductase] + O2 = (R)-ipsdienol + [oxidized NADPH—hemoprotein reductase] + H2O | |||||||||||||||||||||||||||||
For diagram of acyclic monoterpenoid biosynthesis, click here | ||||||||||||||||||||||||||||||
Glossary: | myrcene = 7-methyl-3-methyleneocta-1,6-diene ipsdienol = 2-methyl-6-methyleneocta-2,7-dien-4-ol |
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Other name(s): | myrcene hydroxylase; CYP9T2; CYP9T3 | |||||||||||||||||||||||||||||
Systematic name: | myrcene,NADPH—hemoprotein reductase:O2 oxidoreductase (hydroxylating) | |||||||||||||||||||||||||||||
Comments: | A cytochrome P-450 heme-thiolate protein. Involved in the insect aggregation pheromone production. Isolated from the pine engraver beetle, Ips pini. A small amount of (S)-ipsdienol is also formed. In vitro it also hydroxylated (+)- and (–)-α-pinene, 3-carene, and (+)-limonene, but not α-phellandrene, (–)-β-pinene, γ-terpinene, or terpinolene. | |||||||||||||||||||||||||||||
Links to other databases: | BRENDA, EXPASY, KEGG, MetaCyc | |||||||||||||||||||||||||||||
References: |
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EC | 1.14.14.143 | Relevance: 21.9% | ||||||||||||||||||||||||||||
Accepted name: | (+)-menthofuran synthase | |||||||||||||||||||||||||||||
Reaction: | (+)-pulegone + [reduced NADPH—hemoprotein reductase] + O2 = (+)-menthofuran + [oxidized NADPH—hemoprotein reductase] + H2O | |||||||||||||||||||||||||||||
For diagram of (–)-carvone, perillyl aldehyde and pulegone biosynthesis, click here and for mechanism of reaction, click here | ||||||||||||||||||||||||||||||
Other name(s): | menthofuran synthase; (+)-pulegone 9-hydroxylase; (+)-MFS; cytochrome P450 menthofuran synthase | |||||||||||||||||||||||||||||
Systematic name: | (+)-pulegone,[reduced NADPH—hemoprotein reductase]:oxygen oxidoreductase (9-hydroxylating) | |||||||||||||||||||||||||||||
Comments: | A cytochrome P-450 (heme-thiolate) protein. The conversion of substrate into product involves the hydroxylation of the syn-methyl (C9), intramolecular cyclization to the hemiketal and dehydration to the furan [1]. This is the second cytochrome P-450-mediated step of monoterpene metabolism in peppermint, with the other step being catalysed by EC 1.14.14.99, (S)-limonene 3-monooxygenase [1]. | |||||||||||||||||||||||||||||
Links to other databases: | BRENDA, EXPASY, KEGG, MetaCyc | |||||||||||||||||||||||||||||
References: |
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