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(10,11R)-dihydrogeranylgeranyl diphosphate
(1S,12R)-11,12-dihydroisocembrene + diphosphate
-
-
-
-
?
(10,11S)-dihydrogeranylgeranyl diphosphate
(1S,12S)-11,12-dihydroisocembrene + diphosphate
-
-
-
-
?
(2E,6E,10Z)-geranylgeranyl diphosphate
(1S,11,12Z)-isocembrene + diphosphate
-
-
-
-
?
(E,E,E)-geranylgeranyl diphosphate
taxa-4(5),11(12)-diene + diphosphate
-
first committed step of taxol biosynthesis
-
-
?
(E,E,E)-geranylgeranyl diphosphate
taxa-4,11-diene + diphosphate
-
mechanism of cyclization. Incubation of (R)-[4-2H1]geranylgeranyl diphosphate gives a 10:10:80 mixture of [5beta-2H1]taxa-3(4),11(12)-diens, [5beta-2H1]taxa-4(20),11(12)-diene and unlabeled taxa-4(5),11(12)-diene
-
-
?
11-desmethylgeranylgeranyl diphosphate
(1S)-12-desmethylisocembrene + diphosphate
-
-
-
-
?
7-desmethylgeranylgeranyl diphosphate
(1S,4E,8E,14R,15S)-1,8,14,15-tetramethylbicyclo[9.3.1]pentadeca-4,8,11-triene + diphosphate
-
-
-
-
?
7-desmethylgeranylgeranyl diphosphate
(3E,7E,11S,12R)-4,11,12,15-tetramethylbicyclo[9.3.1]pentadeca-1(15),3,7-triene + diphosphate
-
-
-
-
?
7-desmethylgeranylgeranyl diphosphate
(6E,10E)-11,15-dimethyl-3-methylidenehexadeca-1,6,10,14-tetraene + diphosphate
-
product may be an artefact, but non is formed when enzyme is not present
-
-
?
7-fluorogeranylgeranyl diphosphate
(1R,3E,7Z,11R)-7-fluoro-4,8,12,15,15-pentamethyl-bicyclo[9.3.1]pentadeca-3,7,12-triene
-
-
i.e. endo-7-fluoroverticillene, 25% yield
-
?
7-fluorogeranylgeranyl diphosphate
(1S,3E,7Z,11R)-7-fluoro-4,8,15,15-tetramethyl-12-methylene-bicyclo[9.3.1]pentadeca-3,7-diene
-
verticille-12-yl carbocation intermediate with an 11R stereocenter, the reaction gives three main products and two further isomers
i.e. exo-7-fluoroverticillene, 37% yield
-
?
7-fluorogeranylgeranyl diphosphate
4(20)-methylene-7-fluoroverticillene
-
-
i.e. 4(20)-methylene-7-fluoroverticillene, 26% yield
-
?
cyclopropylidene
?
-
-
-
-
?
geranylgeranyl diphosphate
taxa-4(20),11(12)-diene + diphosphate
-
taxa-4(20),11(12)-diene is formed as a small amount
-
?
geranylgeranyl diphosphate
taxa-4(5),11(12)-diene + diphosphate
geranylgeranyl diphosphate
taxa-4,11-diene + diphosphate
additional information
?
-
geranylgeranyl diphosphate
taxa-4(5),11(12)-diene + diphosphate
-
-
-
?
geranylgeranyl diphosphate
taxa-4(5),11(12)-diene + diphosphate
-
-
-
?
geranylgeranyl diphosphate
taxa-4(5),11(12)-diene + diphosphate
-
-
-
?
geranylgeranyl diphosphate
taxa-4(5),11(12)-diene + diphosphate
-
-
-
?
geranylgeranyl diphosphate
taxa-4(5),11(12)-diene + diphosphate
-
-
-
?
geranylgeranyl diphosphate
taxa-4(5),11(12)-diene + diphosphate
-
-
-
?
geranylgeranyl diphosphate
taxa-4(5),11(12)-diene + diphosphate
-
-
-
?
geranylgeranyl diphosphate
taxa-4(5),11(12)-diene + diphosphate
-
-
?
geranylgeranyl diphosphate
taxa-4(5),11(12)-diene + diphosphate
-
-
-
?
geranylgeranyl diphosphate
taxa-4(5),11(12)-diene + diphosphate
-
taxadiene biosynthetic pathway
precursor of the chemotherapeutic agent taxol
-
ir
geranylgeranyl diphosphate
taxa-4(5),11(12)-diene + diphosphate
-
-
product is biochemically synthesized using truncated TS recombinant protein from Escherichia coli, labeling reveals that 10% substrate is converted to the product
-
?
geranylgeranyl diphosphate
taxa-4,11-diene + diphosphate
-
-
-
-
?
geranylgeranyl diphosphate
taxa-4,11-diene + diphosphate
-
-
-
-
?
geranylgeranyl diphosphate
taxa-4,11-diene + diphosphate
-
-
-
-
?
geranylgeranyl diphosphate
taxa-4,11-diene + diphosphate
-
-
-
-
?
geranylgeranyl diphosphate
taxa-4,11-diene + diphosphate
-
-
-
?
geranylgeranyl diphosphate
taxa-4,11-diene + diphosphate
-
-
-
?
geranylgeranyl diphosphate
taxa-4,11-diene + diphosphate
-
the first committed step toward taxanes and taxol biosynthesis involves taxadiene synthase which promotes the cyclization of geranylgeranyl diphosphate leading to the taxane skeleton
the product of the biosynthetic step is not a limiting substrate in taxol formation
-
?
geranylgeranyl diphosphate
taxa-4,11-diene + diphosphate
-
-
-
?
geranylgeranyl diphosphate
taxa-4,11-diene + diphosphate
-
-
-
-
?
geranylgeranyl diphosphate
taxa-4,11-diene + diphosphate
-
-
-
?
geranylgeranyl diphosphate
taxa-4,11-diene + diphosphate
-
-
-
-
?
geranylgeranyl diphosphate
taxa-4,11-diene + diphosphate
-
-
-
?
geranylgeranyl diphosphate
taxa-4,11-diene + diphosphate
-
catalyzes the first step in taxol biosynthesis
-
?
geranylgeranyl diphosphate
taxa-4,11-diene + diphosphate
-
catalyzes the first step in taxol biosynthesis
-
?
geranylgeranyl diphosphate
taxa-4,11-diene + diphosphate
-
catalyzes the first step in taxol biosynthesis
-
?
geranylgeranyl diphosphate
taxa-4,11-diene + diphosphate
-
catalyzes the first step in taxol biosynthesis
-
?
geranylgeranyl diphosphate
taxa-4,11-diene + diphosphate
-
catalyzes the first step in taxol biosynthesis
-
?
geranylgeranyl diphosphate
taxa-4,11-diene + diphosphate
-
catalyzes the first step in taxol biosynthesis
-
?
geranylgeranyl diphosphate
taxa-4,11-diene + diphosphate
catalyzes the first step in taxol biosynthesis
-
?
geranylgeranyl diphosphate
taxa-4,11-diene + diphosphate
-
isocembrenyl cation is possibly an intermediate in the cyclization of geranylgeranyl diphosphate to taxadiene
-
-
?
geranylgeranyl diphosphate
taxa-4,11-diene + diphosphate
-
catalyzes the first step in taxol biosynthesis
-
?
geranylgeranyl diphosphate
taxa-4,11-diene + diphosphate
-
-
-
?
geranylgeranyl diphosphate
taxa-4,11-diene + diphosphate
-
-
-
-
?
additional information
?
-
-
the wild-type enzyme forms cembrene A as a side product, while enzyme mutant W753H produces cembrene A as main product
-
-
?
additional information
?
-
the wild-type enzyme forms cembrene A as a side product, while enzyme mutant W753H produces cembrene A as main product
-
-
?
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(E,E,E)-geranylgeranyl diphosphate
taxa-4(5),11(12)-diene + diphosphate
-
first committed step of taxol biosynthesis
-
-
?
geranylgeranyl diphosphate
taxa-4(5),11(12)-diene + diphosphate
-
taxadiene biosynthetic pathway
precursor of the chemotherapeutic agent taxol
-
ir
geranylgeranyl diphosphate
taxa-4,11-diene + diphosphate
geranylgeranyl diphosphate
taxa-4,11-diene + diphosphate
-
-
-
-
?
geranylgeranyl diphosphate
taxa-4,11-diene + diphosphate
-
-
-
-
?
geranylgeranyl diphosphate
taxa-4,11-diene + diphosphate
-
-
-
-
?
geranylgeranyl diphosphate
taxa-4,11-diene + diphosphate
-
-
-
-
?
geranylgeranyl diphosphate
taxa-4,11-diene + diphosphate
-
-
-
?
geranylgeranyl diphosphate
taxa-4,11-diene + diphosphate
-
-
-
?
geranylgeranyl diphosphate
taxa-4,11-diene + diphosphate
-
the first committed step toward taxanes and taxol biosynthesis involves taxadiene synthase which promotes the cyclization of geranylgeranyl diphosphate leading to the taxane skeleton
the product of the biosynthetic step is not a limiting substrate in taxol formation
-
?
geranylgeranyl diphosphate
taxa-4,11-diene + diphosphate
-
-
-
?
geranylgeranyl diphosphate
taxa-4,11-diene + diphosphate
-
-
-
-
?
geranylgeranyl diphosphate
taxa-4,11-diene + diphosphate
-
-
-
?
geranylgeranyl diphosphate
taxa-4,11-diene + diphosphate
-
-
-
-
?
geranylgeranyl diphosphate
taxa-4,11-diene + diphosphate
-
-
-
?
geranylgeranyl diphosphate
taxa-4,11-diene + diphosphate
-
catalyzes the first step in taxol biosynthesis
-
?
geranylgeranyl diphosphate
taxa-4,11-diene + diphosphate
-
catalyzes the first step in taxol biosynthesis
-
?
geranylgeranyl diphosphate
taxa-4,11-diene + diphosphate
-
catalyzes the first step in taxol biosynthesis
-
?
geranylgeranyl diphosphate
taxa-4,11-diene + diphosphate
-
catalyzes the first step in taxol biosynthesis
-
?
geranylgeranyl diphosphate
taxa-4,11-diene + diphosphate
-
catalyzes the first step in taxol biosynthesis
-
?
geranylgeranyl diphosphate
taxa-4,11-diene + diphosphate
-
catalyzes the first step in taxol biosynthesis
-
?
geranylgeranyl diphosphate
taxa-4,11-diene + diphosphate
catalyzes the first step in taxol biosynthesis
-
?
geranylgeranyl diphosphate
taxa-4,11-diene + diphosphate
-
catalyzes the first step in taxol biosynthesis
-
?
geranylgeranyl diphosphate
taxa-4,11-diene + diphosphate
-
-
-
?
geranylgeranyl diphosphate
taxa-4,11-diene + diphosphate
-
-
-
-
?
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Hezari, M.; Ketchum, R.E.B.; Gibson, D.M.; Croteau, R.
Taxol production and taxadiene synthase activity in Taxus canadensis cell suspension cultures
Arch. Biochem. Biophys.
337
185-190
1997
Taxus brevifolia, Taxus canadensis
brenda
Wildung, M.R.; Croteau, R.
A cDNA clone for taxadiene synthase, the diterpene cyclase that catalyzes the committed step of taxol biosynthesis
J. Biol. Chem.
271
9201-9204
1996
Taxus brevifolia (Q41594), Taxus brevifolia
brenda
Koepp, A.E.; Hezari, M.; Zajicek, J.; Stofer Vogel, B.; LaFever, R.; Lewis, N.G.; Croteau, R.
Cyclization of geranylgeranyl diphosphateto taxa-4(5),-11(12)-diene is the comitted step of taxol biosynthesis in pacific yew
J. Biol. Chem.
270
8686-8690
1995
Taxus brevifolia
brenda
Lin, X.; Hezari, M.; Koepp, A.E.; Floss, H.G.; Croteau, R.
Mechanism of taxadiene synthase, a diterpene cyclase that catalyzes the first step of taxol biosynthesis in pacific yew
Biochemistry
35
2968-2977
1996
Taxus brevifolia
brenda
Williams, D.C.; Carroll, B.J.; Jin, Q.; Rithner, C.D.; Lenger, S.R.; Floss, H.G.; Coates, R.M.; Williams, R.M.; Croteau, R.
Intramolecular proton transfer in the cyclization of geranylgeranyl diphosphate to the taxadiene precursor of taxol catalyzed by recombinant taxadiene synthase
Chem. Biol.
7
969-977
2000
Taxus brevifolia
brenda
Williams, D.C.; Wildung, M.R.; Jin, A.Q.; Dalal, D.; Oliver, J.S.; Coates, R.M.; Croteau, R.
Heterologous xpression and characterization of a "Pseudomature" form of taxadiene synthase involved in paclitaxel (taxol) biosynthesis and evaluation of a potential intermediate and inhibitors of the multistep diterpene cyclization reaction
Arch. Biochem. Biophys.
379
137-146
2000
Taxus brevifolia
brenda
Huang, Q.; Roessner, C.A.; Croteau, R.; Scott, A.I.
Engineering Escherichia coli for the synthesis of taxadiene, a key intermediate in the biosynthesis of taxol
Bioorg. Med. Chem.
9
2237-2242
2001
Taxus brevifolia
brenda
Huang, Q.; Williams, H.J.; Roessner, C.A.; Scott, A.I.
Sesquiterpenes produced by truncated taxadiene synthase
Tetrahedron Lett.
41
9701-9704
2000
Taxus brevifolia
-
brenda
Jin, Y.; Williams, D.C.; Croteau, R.; Coates, R.M.
Taxadiene synthase-catalyzed cyclization of 6-fluorogeranylgeranyl diphosphate to 7-fluoroverticillenes
J. Am. Chem. Soc.
127
7834-7842
2005
Taxus brevifolia
brenda
Jin, Q.; Williams, D.C.; Hezari, M.; Croteau, R.; Coates, R.M.
Stereochemistry of the macrocyclization and elimination steps in taxadiene biosynthesis through deuterium labeling
J. Org. Chem.
70
4667-4675
2005
Taxus brevifolia
brenda
Chow, S.Y.; Williams, H.J.; Huang, Q.; Nanda, S.; Scott, A.I.
Studies on taxadiene synthase: interception of the cyclization cascade at the isocembrene stage with GGPP analogues
J. Org. Chem.
70
9997-10003
2005
Taxus brevifolia
brenda
Zhou, X.; Wang, Z.; Jiang, K.; Wei, Y.; Lin, J.; Sun, X.; Tang, K.
Screening of taxol-producing endophytic fungi from Taxus chinensis var. mairei
Appl. Biochem. Microbiol.
43
439-443
2007
Alternaria sp., Mucor sp., Ozonium
-
brenda
Hu, F.; Huang, J.; Xu, Y.; Qian, X.; Zhong, J.J.
Responses of defense signals, biosynthetic gene transcription and taxoid biosynthesis to elicitation by a novel synthetic jasmonate in cell cultures of Taxus chinensis
Biotechnol. Bioeng.
94
1064-1071
2006
Taxus chinensis (Q9FT37), Taxus chinensis
brenda
Chow, S.Y.; Williams, H.J.; Pennington, J.D.; Nanda, S.; Reibenspies, J.H.; Scott, A.I.
Studies on taxadiene synthase: interception of the cyclization cascade at the verticillene stage and rearrangement to phomactatriene
Tetrahedron
63
6204-6209
2007
Phoma sp.
-
brenda
Kovacs, K.; Zhang, L.; Linforth, R.S.; Whittaker, B.; Hayes, C.J.; Fray, R.G.
Redirection of carotenoid metabolism for the efficient production of taxadiene [taxa-4(5),11(12)-diene] in transgenic tomato fruit
Transgenic Res.
16
121-126
2007
Taxus baccata (Q93YA3)
brenda
Rontein, D.; Onillon, S.; Herbette, G.; Lesot, A.; Werck-Reichhart, D.; Sallaud, C.; Tissier, A.
CYP725A4 from yew catalyzes complex structural rearrangement of taxa-4(5),11(12)-diene into the yclic ether 5(12)-oxa-3(11)-cyclotaxane
J. Biol. Chem.
283
6067-6075
2008
Taxus cuspidata
brenda
Engels, B.; Dahm, P.; Jennewein, S.
Metabolic engineering of taxadiene biosynthesis in yeast as a first step towards Taxol (Paclitaxel) production
Metab. Eng.
10
201-206
2008
Taxus chinensis
brenda
Exposito, O.; Bonfill, M.; Onrubia, M.; Jane, A.; Moyano, E.; Cusido, R.M.; Palazon, J.; Pinol, M.T.
Effect of taxol feeding on taxol and related taxane production in Taxus baccata suspension cultures
N. Biotechnol.
25
252-259
2008
Taxus baccata
brenda
Staniek, A.; Woerdenbag, H.J.; Kayser, O.
Taxomyces andreanae: a presumed paclitaxel producer demystified?
Planta Med.
75
1561-1566
2009
Taxomyces andreanae, Taxomyces andreanae CBS 27992
brenda
Anterola, A.; Shanle, E.; Perroud, P.F.; Quatrano, R.
Production of taxa-4(5),11(12)-diene by transgenic Physcomitrella patens
Transgenic Res.
18
655-660
2009
Taxus brevifolia
brenda
Koeksal, M.; Jin, Y.; Coates, R.M.; Croteau, R.; Christianson, D.W.
Taxadiene synthase structure and evolution of modular architecture in terpene biosynthesis
Nature
469
116-120
2011
Taxus brevifolia (Q41594), Taxus brevifolia
brenda
Cha, M.; Shim, S.H.; Kim, S.H.; Kim, O.T.; Lee, S.W.; Kwon, S.Y.; Baek, K.H.
Production of taxadiene from cultured ginseng roots transformed with taxadiene synthase gene
BMB Rep.
45
589-594
2012
Taxus brevifolia (Q41594), Taxus brevifolia
brenda
Hasan, M.M.; Kim, H.S.; Jeon, J.H.; Kim, S.H.; Moon, B.; Song, J.Y.; Shim, S.H.; Baek, K.H.
Metabolic engineering of Nicotiana benthamiana for the increased production of taxadiene
Plant Cell Rep.
33
895-904
2014
Taxus brevifolia (Q41594), Taxus brevifolia
brenda
Edgar, S.; Li, F.S.; Qiao, K.; Weng, J.K.; Stephanopoulos, G.
Engineering of taxadiene synthase for improved selectivity and yield of a key taxol biosynthetic intermediate
ACS Synth. Biol.
6
201-205
2017
Taxus brevifolia (Q41594)
brenda
Freud, Y.; Ansbacher, T.; Major, D.
Catalytic control in the facile proton transfer in taxadiene synthase
ACS Catal.
7
7653-7657
2017
Taxus brevifolia (Q41594)
-
brenda
Pemberton, T.A.; Chen, M.; Harris, G.G.; Chou, W.K.; Duan, L.; Koeksal, M.; Genshaft, A.S.; Cane, D.E.; Christianson, D.W.
Exploring the influence of domain architecture on the catalytic function of diterpene synthases
Biochemistry
56
2010-2023
2017
Taxus brevifolia
brenda
Ansbacher, T.; Freud, Y.; Major, D.
Slow-starter enzymes role of active-site architecture in the catalytic control of the biosynthesis of taxadiene by taxadiene synthase
Biochemistry
57
3773-3779
2018
Taxus brevifolia, Taxus brevifolia (Q41594)
brenda
Li, M.; Jiang, F.; Yu, X.; Miao, Z.
Engineering isoprenoid biosynthesis in Artemisia annua L. for the production of taxadiene a key intermediate of taxol
BioMed Res. Int.
2015
504932
2015
Taxus brevifolia (Q41594)
brenda
Soliman, S.; Tang, Y.
Natural and engineered production of taxadiene with taxadiene synthase
Biotechnol. Bioeng.
112
229-235
2015
Taxus brevifolia
brenda
Escorcia, A.M.; van Rijn, J.P.M.; Cheng, G.J.; Schrepfer, P.; Brueck, T.B.; Thiel, W.
Molecular dynamics study of taxadiene synthase catalysis
J. Comput. Chem.
39
1215-1225
2018
Taxus brevifolia (Q41594)
brenda
Syklowska-Baranek, K.; Pilarek, M.; Bonfill, M.; Kafel, K.; Pietrosiuk, A.
Perfluorodecalin-supported system enhances taxane production in hairy root cultures of Taxus xxa0media var. Hicksii carrying a taxadiene synthase transgene
Plant Cell Tissue Organ Cult.
120
1051-1059
2015
Taxus baccata (Q6TBY0)
-
brenda