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Farnesol
germacrene D
Conditions | Yield |
---|---|
With sodium carbonate; magnesium chloride In terpene synthase buffer at 25℃; for 18h; pH=10; Enzymatic reaction; | 91.1% |
Farnesol
A
delta-cadinene
B
germacrene D
Conditions | Yield |
---|---|
With sodium acetate; magnesium chloride In terpene synthase buffer at 25℃; for 18h; pH=5; Enzymatic reaction; | A 12.32% B 84.3% |
Farnesol
C
delta-cadinene
D
germacrene D
Conditions | Yield |
---|---|
With potassium chloride In terpene synthase buffer at 25℃; for 18h; pH=8; Enzymatic reaction; | A 10.7% B 34.2% C 15% D 19.4% E 10.3% |
Farnesol
D
delta-cadinene
E
germacrene D
Conditions | Yield |
---|---|
With potassium chloride In terpene synthase buffer at 37℃; for 18h; pH=8; Enzymatic reaction; | A 5.3% B 7.1% C 22.3% D 13.3% E 22.3% F 12.3% |
farnesyl pyrophosphate
germacrene D
Conditions | Yield |
---|---|
With germacradienol synthase SC9B1.20; 2-hydroxyethanethiol In pentane at 30℃; for 24h; | 1.6 mg |
With (S)-germacrene D synthase; 3-[(3-cholamidopropyl)dimethylammonio]propanesulfonate; glycerol; 2-amino-2-hydroxymethyl-1,3-propanediol; 2-hydroxyethanethiol; magnesium chloride In chloroform-d1; water at 25℃; for 24h; pH=7.5; Enzymatic reaction; | |
With Y406F-GDS-His6 In pentane at 20℃; for 120h; pH=7.5; Kinetics; Enzymatic reaction; |
(2E,6E)-<1,1-2H2>-farnesyl diphosphate
D
germacrene D
Conditions | Yield |
---|---|
With Streptomyces coelicolor germacradienol synthase; Tris-Cl; magnesium chloride In water-d2 at 30℃; Enzymatic reaction; |
farnesyl pyrophosphate
B
(-)-geosmin
C
germacrene D
Conditions | Yield |
---|---|
With Streptomyces coelicolor germacradienol synthase; Tris-Cl; magnesium chloride In water at 30℃; for 4h; Enzymatic reaction; |
farnesyl pyrophosphate
A
4α-hydroxygermacra-1(10),5-diene
B
alloaromadendrene
C
germacrene D
Conditions | Yield |
---|---|
With recombinant (His)8-tagged Medicago truncatula MtTPS5 sesquiterpene synthase Y526F mutant; water; magnesium chloride In pentane at 30℃; for 1.5h; pH=7.5; Mechanism; aq. buffer; Enzymatic reaction; optical yield given as %ee; stereospecific reaction; |
farnesyl pyrophosphate
A
δ-cadinol
C
germacrene D
D
(-)-(1R,4S,5R,6R,7S,10R)-7-isopropyl-4,10-dimethyl-tricyclo[4.4.0.01,5]decane-4-ol
Conditions | Yield |
---|---|
With recombinant (His)8-tagged Medicago truncatula MtTPS5 sesquiterpene synthase; water; magnesium chloride In pentane at 30℃; for 1.5h; pH=7.5; Mechanism; aq. buffer; Enzymatic reaction; optical yield given as %ee; stereospecific reaction; |
3-methyl-2-buten-1-ol
germacrene D
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: Escherichia coli hydroxyethylthiazole kinase; ATP; pyruvate kinase / aq. buffer / 16 h / 20 °C / pH 8 / Enzymatic reaction 2: isopentenyl phosphate kinase from Methanocaldococcus jannaschii; ATP; pyruvate kinase / aq. buffer / 16 h / 20 °C / pH 8 / Enzymatic reaction 3: (2E,6E)-FDP synthase from Geobacillus stearothermophilus; (-)-germacrene D synthase from Solidago canadensis; 1,4-dithio-L-threitol; magnesium chloride / aq. buffer / 16 h / 20 °C / pH 8 / Enzymatic reaction View Scheme |
2-methyl-1-buten-4-ol
germacrene D
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: Escherichia coli hydroxyethylthiazole kinase; ATP; pyruvate kinase / aq. buffer / 16 h / 20 °C / pH 8 / Enzymatic reaction 2: isopentenyl phosphate kinase from Methanocaldococcus jannaschii; ATP; pyruvate kinase / aq. buffer / 16 h / 20 °C / pH 8 / Enzymatic reaction 3: (2E,6E)-FDP synthase from Geobacillus stearothermophilus; (-)-germacrene D synthase from Solidago canadensis; 1,4-dithio-L-threitol; magnesium chloride / aq. buffer / 16 h / 20 °C / pH 8 / Enzymatic reaction View Scheme |
3-methylbut-2-enyl hydrogen phosphate
germacrene D
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: isopentenyl phosphate kinase from Methanocaldococcus jannaschii; ATP; pyruvate kinase / aq. buffer / 16 h / 20 °C / pH 8 / Enzymatic reaction 2: (2E,6E)-FDP synthase from Geobacillus stearothermophilus; (-)-germacrene D synthase from Solidago canadensis; 1,4-dithio-L-threitol; magnesium chloride / aq. buffer / 16 h / 20 °C / pH 8 / Enzymatic reaction View Scheme |
phosphoric acid mono(3-methylbut-3-enyl) ester
germacrene D
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: isopentenyl phosphate kinase from Methanocaldococcus jannaschii; ATP; pyruvate kinase / aq. buffer / 16 h / 20 °C / pH 8 / Enzymatic reaction 2: (2E,6E)-FDP synthase from Geobacillus stearothermophilus; (-)-germacrene D synthase from Solidago canadensis; 1,4-dithio-L-threitol; magnesium chloride / aq. buffer / 16 h / 20 °C / pH 8 / Enzymatic reaction View Scheme |
Conditions | Yield |
---|---|
With 1,4-dithio-L-threitol; (-)-germacrene D synthase from Solidago canadensis; (2E,6E)-FDP synthase from Geobacillus stearothermophilus; magnesium chloride In aq. buffer at 20℃; for 16h; pH=8; Enzymatic reaction; |
germacrene D
(-)-Mintsulfide
Conditions | Yield |
---|---|
With hydrocarbon solvent; sulfur Irradiation; | 50% |
germacrene D
(1S,3aS,4S,7aR)-4-Bromo-3a-methyl-7-methylene-1-(2-methyl-propenyl)-octahydro-indene
((3R,3aS,8S,8aS)-8-Bromo-3-isopropyl-8a-methyl-1,2,3,3a,6,7,8,8a-octahydro-azulen-5-yl)-methanol
1-((1S,3aR,4R,7aS)-4-Bromo-3a-methyl-7-methylene-octahydro-inden-1-yl)-2-methyl-propan-1-ol
(1R,4R,4aS,8aS)-6-Bromomethyl-4-isopropyl-1-methyl-1,2,3,4,4a,7,8,8a-octahydro-naphthalen-1-ol
Conditions | Yield |
---|---|
With N-Bromosuccinimide In tetrahydrofuran; water for 0.5h; Ambient temperature; Further byproducts given; | A 4.2% B 11% C 13.3% D 7.2% |
germacrene D
((3R,3aS,8S,8aS)-8-Bromo-3-isopropyl-8a-methyl-1,2,3,3a,6,7,8,8a-octahydro-azulen-5-yl)-methanol
1-((1S,3aR,4R,7aS)-4-Bromo-3a-methyl-7-methylene-octahydro-inden-1-yl)-2-methyl-propan-1-ol
1-((1R,3aR,4R,7aS)-4-Bromo-3a-methyl-7-methylene-octahydro-inden-1-yl)-2-methyl-propan-2-ol
(1R,4R,4aS,8aS)-6-Bromomethyl-4-isopropyl-1-methyl-1,2,3,4,4a,7,8,8a-octahydro-naphthalen-1-ol
Conditions | Yield |
---|---|
With N-Bromosuccinimide In tetrahydrofuran; water for 0.5h; Ambient temperature; Further byproducts given; | A 11% B 13.3% C 2.7% D 7.2% |
germacrene D
((3R,3aS,8S,8aS)-8-Bromo-3-isopropyl-8a-methyl-1,2,3,3a,6,7,8,8a-octahydro-azulen-5-yl)-methanol
1-((1S,3aR,4R,7aS)-4-Bromo-3a-methyl-7-methylene-octahydro-inden-1-yl)-2-methyl-propan-1-ol
(1S,2S,4aR,5R,8aS)-5-Bromo-2-isopropyl-4a-methyl-8-methylene-decahydro-naphthalen-1-ol
(1R,4R,4aS,8aS)-6-Bromomethyl-4-isopropyl-1-methyl-1,2,3,4,4a,7,8,8a-octahydro-naphthalen-1-ol
Conditions | Yield |
---|---|
With N-Bromosuccinimide In tetrahydrofuran; water for 0.5h; Ambient temperature; Further byproducts given; | A 11% B 13.3% C 4.9% D 7.2% |
germacrene D
((3R,3aS,8S,8aS)-8-Bromo-3-isopropyl-8a-methyl-1,2,3,3a,6,7,8,8a-octahydro-azulen-5-yl)-methanol
1-((1S,3aR,4R,7aS)-4-Bromo-3a-methyl-7-methylene-octahydro-inden-1-yl)-2-methyl-propan-1-ol
(1S,4R,4aS,8aS)-6-Bromomethyl-4-isopropyl-1-methyl-1,2,3,4,4a,7,8,8a-octahydro-naphthalen-1-ol
(1R,4R,4aS,8aS)-6-Bromomethyl-4-isopropyl-1-methyl-1,2,3,4,4a,7,8,8a-octahydro-naphthalen-1-ol
Conditions | Yield |
---|---|
With N-Bromosuccinimide In tetrahydrofuran; water for 0.5h; Ambient temperature; Further byproducts given; | A 11% B 13.3% C 7% D 7.2% |
With N-Bromosuccinimide In tetrahydrofuran; water for 0.5h; Ambient temperature; Further byproducts given; | A 11% B 13.3% C 7% D 7.2% |
diazomethane
germacrene D
(+/-)-2-isopropyl-4-acetyl-butyric acid methyl ester
Conditions | Yield |
---|---|
(i) O3, (ii) /BRN= 102415/; Multistep reaction; |
germacrene D
D-germacrene
Conditions | Yield |
---|---|
(hydrogenation); |
germacrene D
(8R)-Isopropyl-(1,5Ξ)-dimethyl-cyclodeca-1-trans,6-trans-dien
Conditions | Yield |
---|---|
With hydrogen; palladium on barium sulfate In ethanol |
germacrene D
γ-muurolene
germacrene D
(+)-γ-cadinene
germacrene D
(1S,3aS,3bR,6aS,6bR)-1-Isopropyl-3a-methyl-6-methylene-decahydro-cyclobutadicyclopentene
Conditions | Yield |
---|---|
(photolysis); |
germacrene D
α-bourbonene
Conditions | Yield |
---|---|
(photolysis); |
germacrene D
(-)-germacrene D
Conditions | Yield |
---|---|
With hydrogen; palladium on barium sulfate In ethanol |
germacrene D
Conditions | Yield |
---|---|
With hydrogen; palladium on barium sulfate In ethanol |
germacrene D
Conditions | Yield |
---|---|
(photolysis); |
germacrene D
ω-cadinene
germacrene D
torilensulfat
Conditions | Yield |
---|---|
With sulfuric acid In diethyl ether at 0℃; for 0.333333h; | 450 mg |
germacrene D
Conditions | Yield |
---|---|
With manganese(IV) oxide In diethyl ether for 1h; | 5 mg |
germacrene D
(E)-(1R,4S,10R)-4-Isopropyl-1-methyl-7-methylene-11-oxa-bicyclo[8.1.0]undec-5-ene
Conditions | Yield |
---|---|
With 3-chloro-benzenecarboperoxoic acid In diethyl ether at -10 - -4℃; | 150 mg |
With 3-chloro-benzenecarboperoxoic acid In diethyl ether at -5 - 0℃; for 1h; |
germacrene D
(1R,7S,E)-7-isopropyl-4,10-dimethylenecyclodec-5-enol
Conditions | Yield |
---|---|
With 3-chloro-benzenecarboperoxoic acid; lithium diisopropyl amide Multistep reaction; | |
Multi-step reaction with 2 steps 1: m-chloroperoxybenzoic acid / diethyl ether / 1 h / -5 - 0 °C 2: 14.8 g / LDA / cyclohexane; diethyl ether / 1) -60 deg C -> room temperature, 2) room temperature, 10 h View Scheme | |
Multi-step reaction with 2 steps 1: 150 mg / m-CPBA / diethyl ether / -10 - -4 °C 2: 17 mg / lithium diisopropylamide / diethyl ether / 1.) 1 h, -74 deg C, 2.) 2 h, r.t. View Scheme |
germacrene D
germacra-4(15),5,10(14)-trien-1-one
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: m-chloroperoxybenzoic acid / diethyl ether / 1 h / -5 - 0 °C 2: 14.8 g / LDA / cyclohexane; diethyl ether / 1) -60 deg C -> room temperature, 2) room temperature, 10 h 3: 39 percent / tert-butyl hydroperoxide, SeO2 / H2O; CH2Cl2 / 24 h / 30 - 35 °C View Scheme | |
Multi-step reaction with 2 steps 1: 1.) MCPBA, 2.) LDA 2: 30 percent / TBHP, SeO2 View Scheme |
germacrene D
(E)-(7S,9S)-9-Hydroxy-7-isopropyl-4,10-dimethylene-cyclodec-5-enone
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: m-chloroperoxybenzoic acid / diethyl ether / 1 h / -5 - 0 °C 2: 14.8 g / LDA / cyclohexane; diethyl ether / 1) -60 deg C -> room temperature, 2) room temperature, 10 h 3: 21 percent / tert-butyl hydroperoxide, SeO2 / H2O; CH2Cl2 / 24 h / 30 - 35 °C View Scheme | |
Multi-step reaction with 2 steps 1: 1.) MCPBA, 2.) LDA 2: 21 percent / TBHP, SeO2 View Scheme |
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