Any feedback?
Please rate this page
(literature.php)
(0/150)

BRENDA support

Literature summary extracted from

  • 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 (2008), J. Biol. Chem., 283, 6067-6075.
    View publication on PubMed

Application

EC Number Application Comment Organism
1.14.14.176 drug development paclitaxel is a successful anticancer drug Taxus cuspidata
4.2.3.17 drug development paclitaxel is a successful anticancer drug Taxus cuspidata

Cloned(Commentary)

EC Number Cloned (Comment) Organism
1.14.14.176 cDNAs encoding taxa-4(5),11(12)-diene synthase and CYP725A4 are introduced in Nicotiana sylvestris for specific expression in trichome cells. Production of truncated TS in Escherichia coli. The TS cDNA coding for a protein truncated at the N-terminus at amino acid position 75 is cloned in the pET-30b expression vector. Furthermore, CYP725A4 is expressed in yeast. Taxus cuspidata
1.14.14.176 CYP725A4, DNA and amino acid sequence determination and analysis, expression in the Saccharomyces cerevisiae WAT11 strain containing the Arabidopsis reductase ATR1, and co-expression in Nicotiana sylvestris with taxa-4(5),11(12)-diene synthase, which does not lead to 5alpha-hydroxytaxa-4(20),11(12)-diene, but to formation of 5(12)-oxa-3(11)-cyclotaxane, a tritiated oxidized taxane, structural analysis of the compound, phenotype, overview Taxus cuspidata
4.2.3.17 cDNA encoding taxa-4(5),11(12)-diene synthase is introduced in Nicotiana sylvestris for specific expression in trichome cells. Taxus cuspidata

KM Value [mM]

EC Number KM Value [mM] KM Value Maximum [mM] Substrate Comment Organism Structure
1.14.14.176 0.0069
-
 taxa-4(5),11(12)-diene
-
 Taxus cuspidata

Natural Substrates/ Products (Substrates)

EC Number Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
1.14.14.176 additional information Taxus cuspidata cDNAs encoding taxa-4(5),11(12)-diene synthase and CYP725A4 are introduced in Nicotiana sylvestris for specific expression in trichome cells. The co-expression does not lead to the production of the expected 5-hydroxytaxa-4(20),11(12)-diene. Instead, taxa-4(5),11(12)-diene is quantitatively converted to a novel taxane ?
-
 ?
1.14.14.176 taxa-4(5),11(12)-diene + [reduced NADPH-hemoprotein reductase] + O2 Taxus cuspidata hydroxylation of the C-5alpha is the first of the oxidations resulting in taxol 5(12)-oxa-3(11)-cyclotaxane + [oxidized NADPH-hemoprotein reductase] + H2O OCT is a cyclic ether ?
1.14.14.176 taxa-4,11-diene + [reduced NADPH-hemoprotein reductase] + O2 Taxus cuspidata
-
 taxa-4(20),11-dien-5alpha-ol + [oxidized NADPH-hemoprotein reductase] + H2O
-
 ?
4.2.3.17 geranylgeranyl diphosphate Taxus cuspidata
-
 taxa-4,11-diene + diphosphate
-
 ?

Organism

EC Number Organism UniProt Comment Textmining
1.14.14.176 Taxus cuspidata Q6WG30
-
-
4.2.3.17 Taxus cuspidata
-
-
-

Purification (Commentary)

EC Number Purification (Comment) Organism
4.2.3.17 Purification of the recombinant truncated TS protein as histag is performed using nickel-nitrilotriacetic acid affinity chromatography Taxus cuspidata

Reaction

EC Number Reaction Comment Organism Reaction ID
1.14.14.176 taxa-4,11-diene + [reduced NADPH-hemoprotein reductase] + O2 = taxa-4(20),11-dien-5alpha-ol + [oxidized NADPH-hemoprotein reductase] + H2O reaction mechanism Taxus cuspidata
a

Source Tissue

EC Number Source Tissue Comment Organism Textmining
1.14.14.176 leaf
-
 Taxus cuspidata
-

Substrates and Products (Substrate)

EC Number Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
1.14.14.176 additional information the recombinant enzyme produces 5(12)-oxa-3(11)-cyclotaxane, a tritiated oxidized taxane, instead of taxa-4(20),11-dien-5alpha-ol, structural analysis of the compound, overview Taxus cuspidata ?
-
 ?
1.14.14.176 additional information cDNAs encoding taxa-4(5),11(12)-diene synthase and CYP725A4 are introduced in Nicotiana sylvestris for specific expression in trichome cells. The co-expression does not lead to the production of the expected 5-hydroxytaxa-4(20),11(12)-diene. Instead, taxa-4(5),11(12)-diene is quantitatively converted to a novel taxane Taxus cuspidata ?
-
 ?
1.14.14.176 taxa-4(5),11(12)-diene + [reduced NADPH-hemoprotein reductase] + O2 hydroxylation of the C-5alpha is the first of the oxidations resulting in taxol Taxus cuspidata 5(12)-oxa-3(11)-cyclotaxane + [oxidized NADPH-hemoprotein reductase] + H2O OCT is a cyclic ether ?
1.14.14.176 taxa-4,11-diene + [reduced NADPH-hemoprotein reductase] + O2
-
 Taxus cuspidata taxa-4(20),11-dien-5alpha-ol + [oxidized NADPH-hemoprotein reductase] + H2O
-
 ?
4.2.3.17 geranylgeranyl diphosphate
-
 Taxus cuspidata 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 ?
4.2.3.17 geranylgeranyl diphosphate
-
 Taxus cuspidata taxa-4,11-diene + diphosphate
-
 ?

Synonyms

EC Number Synonyms Comment Organism
1.14.14.176 CYP725A4
-
 Taxus cuspidata
1.14.14.176 taxa-4(5),11(12)-diene 5-hydroxylase
-
 Taxus cuspidata
1.14.14.176 taxa-4(5),11(12)-diene 5alpha-hydroxylase
-
 Taxus cuspidata
4.2.3.17 taxa-4(5),11(12)-diene synthase
-
 Taxus cuspidata

Temperature Optimum [°C]

EC Number Temperature Optimum [°C] Temperature Optimum Maximum [°C] Comment Organism
1.14.14.176 30
-
 assay at Taxus cuspidata

Cofactor

EC Number Cofactor Comment Organism Structure
1.14.14.176 NADPH
-
 Taxus cuspidata