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Literature summary for 1.14.14.86 extracted from

  • Mafu, S.; Jia, M.; Zi, J.; Morrone, D.; Wu, Y.; Xu, M.; Hillwig, M.L.; Peters, R.J.
    Probing the promiscuity of ent-kaurene oxidases via combinatorial biosynthesis (2016), Proc. Natl. Acad. Sci. USA, 113, 2526-2531 .
    View publication on PubMedView publication on EuropePMC
Search for more literature for 1.14.14.86

Application

Application Comment Organism
synthesis when KO2 is coexpressed in Escherichia coli engineered to produce ent-kaurene, turnover to entkauren-19-oic acid is observed. In addition, KO2 reacts with ent-isokaurene, and the closely related ent-trachylobane, converting the C4alpha methyl to a mixture of the alcohol and further oxidized carboxylic acid with each substrate Arabidopsis thaliana
synthesis when KO2 is coexpressed in Escherichia coli engineered to produce ent-kaurene, turnover to entkauren-19-oic acid is observed. In addition, KO2 reacts with ent-isokaurene, and the closely related ent-trachylobane, converting the C4alpha methyl to a mixture of the alcohol and further oxidized carboxylic acid with each substrate Oryza sativa Japonica Group

Cloned(Commentary)

Cloned (Comment) Organism
expression in Escherichia coli Arabidopsis thaliana
expression in Escherichia coli Oryza sativa Japonica Group
gene CYP701A3, phylogenetic analysis Arabidopsis thaliana
gene CYP701A6, phylogenetic analysis Oryza sativa Japonica Group

KM Value [mM]

KM Value [mM] KM Value Maximum [mM] Substrate Comment Organism Structure
0.03
-
 isopimara-7,15-diene pH and temperature not specified in the publication Arabidopsis thaliana
0.03
-
 isopimara-8,15-diene pH not specified in the publication, temperature not specified in the publication Arabidopsis thaliana
0.046
-
 ent-sandaracopimaradiene pH and temperature not specified in the publication Arabidopsis thaliana
0.046
-
 ent-sandaracopimaradiene pH not specified in the publication, temperature not specified in the publication Arabidopsis thaliana
0.05
-
 ent-cassadiene pH and temperature not specified in the publication Arabidopsis thaliana
0.05
-
 syn-aphidicolene pH and temperature not specified in the publication Arabidopsis thaliana
0.05
-
 ent-cassadiene pH not specified in the publication, temperature not specified in the publication Arabidopsis thaliana
0.05
-
 syn-aphidicolene pH not specified in the publication, temperature not specified in the publication Arabidopsis thaliana

Localization

Localization Comment Organism GeneOntology No. Textmining
chloroplast
-
 Arabidopsis thaliana 9507
-

Natural Substrates/ Products (Substrates)

Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
ent-kaur-16-en-19-al + [reduced NADPH-hemoprotein reductase] + O2 Arabidopsis thaliana
-
 ent-kaur-16-en-19-oate + [oxidized NADPH-hemoprotein reductase] + H2O
-
 ?
ent-kaur-16-en-19-al + [reduced NADPH-hemoprotein reductase] + O2 Oryza sativa Japonica Group
-
 ent-kaur-16-en-19-oate + [oxidized NADPH-hemoprotein reductase] + H2O
-
 ?
ent-kaur-16-en-19-ol + [reduced NADPH-hemoprotein reductase] + O2 Arabidopsis thaliana
-
 ent-kaur-16-en-19-al + [oxidized NADPH-hemoprotein reductase] + H2O
-
 ?
ent-kaur-16-en-19-ol + [reduced NADPH-hemoprotein reductase] + O2 Oryza sativa Japonica Group
-
 ent-kaur-16-en-19-al + [oxidized NADPH-hemoprotein reductase] + H2O
-
 ?
ent-kaur-16-ene + 3 [reduced NADPH-hemoprotein reductase] + 3 O2 Arabidopsis thaliana overall reaction ent-kaur-16-en-19-oate + 3 [oxidized NADPH-hemoprotein reductase] + 4 H2O
-
 ?
ent-kaur-16-ene + 3 [reduced NADPH-hemoprotein reductase] + 3 O2 Oryza sativa Japonica Group overall reaction ent-kaur-16-en-19-oate + 3 [oxidized NADPH-hemoprotein reductase] + 4 H2O
-
 ?
ent-kaur-16-ene + [reduced NADPH-hemoprotein reductase] + O2 Arabidopsis thaliana
-
 ent-kaur-16-en-19-ol + [oxidized NADPH-hemoprotein reductase] + H2O
-
 ?
ent-kaur-16-ene + [reduced NADPH-hemoprotein reductase] + O2 Oryza sativa Japonica Group
-
 ent-kaur-16-en-19-ol + [oxidized NADPH-hemoprotein reductase] + H2O
-
 ?

Organism

Organism UniProt Comment Textmining
Arabidopsis thaliana Q93ZB2
-
-
Oryza sativa Japonica Group Q5Z5R4
-
-

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
ent-beyerene + [reduced NADPH-hemoprotein reductase] + O2
-
 Arabidopsis thaliana ?
-
 ?
ent-cassadiene + 3 [reduced NADPH-hemoprotein reductase] + 3 O2
-
 Arabidopsis thaliana ent-cassadien-19-oic acid + 3 [oxidized NADPH-hemoprotein reductase] + 4 H2O
-
 ?
ent-cassadiene + [reduced NADPH-hemoprotein reductase] + O2
-
 Arabidopsis thaliana ?
-
 ?
ent-isokaur-16-ene + [reduced NADPH-hemoprotein reductase] + O2
-
 Arabidopsis thaliana ent-isokaur-16-en-19-oate + [oxidized NADPH-hemoprotein reductase] + H2O
-
 ?
ent-isokaur-16-ene + [reduced NADPH-hemoprotein reductase] + O2
-
 Oryza sativa Japonica Group ent-isokaur-16-en-19-oate + [oxidized NADPH-hemoprotein reductase] + H2O
-
 ?
ent-isokaurene + 3 [reduced NADPH-hemoprotein reductase] + 3 O2
-
 Arabidopsis thaliana ent-isokauren-19-oic acid + 3 [oxidized NADPH-hemoprotein reductase] + 4 H2O
-
 ?
ent-isokaurene + 3 [reduced NADPH-hemoprotein reductase] + 3 O2
-
 Oryza sativa Japonica Group ent-isokauren-19-oic acid + 3 [oxidized NADPH-hemoprotein reductase] + 4 H2O
-
 ?
ent-kaur-16-en-19-al + [reduced NADPH-hemoprotein reductase] + O2
-
 Arabidopsis thaliana ent-kaur-16-en-19-oate + [oxidized NADPH-hemoprotein reductase] + H2O
-
 ?
ent-kaur-16-en-19-al + [reduced NADPH-hemoprotein reductase] + O2
-
 Oryza sativa Japonica Group ent-kaur-16-en-19-oate + [oxidized NADPH-hemoprotein reductase] + H2O
-
 ?
ent-kaur-16-en-19-ol + [reduced NADPH-hemoprotein reductase] + O2
-
 Arabidopsis thaliana ent-kaur-16-en-19-al + [oxidized NADPH-hemoprotein reductase] + H2O
-
 ?
ent-kaur-16-en-19-ol + [reduced NADPH-hemoprotein reductase] + O2
-
 Oryza sativa Japonica Group ent-kaur-16-en-19-al + [oxidized NADPH-hemoprotein reductase] + H2O
-
 ?
ent-kaur-16-ene + 3 [reduced NADPH-hemoprotein reductase] + 3 O2
-
 Arabidopsis thaliana ent-kaur-16-en-19-oate + 3 [oxidized NADPH-hemoprotein reductase] + 4 H2O
-
 ?
ent-kaur-16-ene + 3 [reduced NADPH-hemoprotein reductase] + 3 O2
-
 Oryza sativa Japonica Group ent-kaur-16-en-19-oate + 3 [oxidized NADPH-hemoprotein reductase] + 4 H2O
-
 ?
ent-kaur-16-ene + 3 [reduced NADPH-hemoprotein reductase] + 3 O2 overall reaction Arabidopsis thaliana ent-kaur-16-en-19-oate + 3 [oxidized NADPH-hemoprotein reductase] + 4 H2O
-
 ?
ent-kaur-16-ene + 3 [reduced NADPH-hemoprotein reductase] + 3 O2 overall reaction Oryza sativa Japonica Group ent-kaur-16-en-19-oate + 3 [oxidized NADPH-hemoprotein reductase] + 4 H2O
-
 ?
ent-kaur-16-ene + [reduced NADPH-hemoprotein reductase] + O2
-
 Arabidopsis thaliana ent-kaur-16-en-19-ol + [oxidized NADPH-hemoprotein reductase] + H2O
-
 ?
ent-kaur-16-ene + [reduced NADPH-hemoprotein reductase] + O2
-
 Oryza sativa Japonica Group ent-kaur-16-en-19-ol + [oxidized NADPH-hemoprotein reductase] + H2O
-
 ?
ent-sandaracopimaradiene + 3 [reduced NADPH-hemoprotein reductase] + 3 O2
-
 Arabidopsis thaliana ent-sandaracopimaradien-19-oic acid + 3 [oxidized NADPH-hemoprotein reductase] + 4 H2O
-
 ?
ent-sandaracopimaradiene + [reduced NADPH-hemoprotein reductase] + O2
-
 Arabidopsis thaliana ?
-
 ?
ent-trachylobane + 3 [reduced NADPH-hemoprotein reductase] + 3 O2
-
 Arabidopsis thaliana ent-trachyloban-19-oic acid + 3 [oxidized NADPH-hemoprotein reductase] + 4 H2O
-
 ?
ent-trachylobane + 3 [reduced NADPH-hemoprotein reductase] + 3 O2
-
 Oryza sativa Japonica Group ent-trachyloban-19-oic acid + 3 [oxidized NADPH-hemoprotein reductase] + 4 H2O
-
 ?
ent-trachylobane + [reduced NADPH-hemoprotein reductase] + O2
-
 Arabidopsis thaliana ?
-
 ?
ent-trachylobane + [reduced NADPH-hemoprotein reductase] + O2 low activity Oryza sativa Japonica Group ?
-
 ?
isopimara-7,15-diene + [reduced NADPH-hemoprotein reductase] + O2
-
 Arabidopsis thaliana ?
-
 ?
isopimara-8,15-diene + 3 [reduced NADPH-hemoprotein reductase] + 3 O2
-
 Arabidopsis thaliana 3beta-hydroxyisopimara-8,15-diene + 2alpha-hydroxysandaracopimaradiene + 3 [oxidized NADPH-hemoprotein reductase] + 4 H2O
-
 ?
isopimara-8,15-diene + [reduced NADPH-hemoprotein reductase] + O2
-
 Arabidopsis thaliana ?
-
 ?
additional information use of combinatorial biosynthesis enabled analysis of more than 20 potential substrates, starting with (E,E,E)-geranylgeranyl diphosphate, as well as structural characterization of 12 resulting unknown products, determination of hydroxylation positions, structure-function relationship for the activity, and substrate specificity, overview. No activity with ent-pimara-8(14),15-diene, pimara-8,15-diene, miltiradiene, abietaenol, sclarene, labdadienol, and ent-kauran-16beta-ol Arabidopsis thaliana ?
-
 ?
additional information use of combinatorial biosynthesis enabled analysis of more than 20 potential substrates, starting with (E,E,E)-geranylgeranyl diphosphate, as well as structural characterization of 12 resulting unknown products, determination of hydroxylation positions, structure-function relationship for the activity, and substrate specificity, overview. No activity with ent-pimara-8(14),15-diene, pimara-8,15-diene, miltiradiene, abietaenol, sclarene, labdadienol, ent-kauran-16beta-ol, ent-cassadiene, ent-sandaracopimaradiene, syn-aphidicolene, isopimara-7,15-diene, ent-beyerene, syn-pimara-7,15-diene, syn-stemarene, syn-stemodene, syn-labdatriene, syn-pimara-9(11),15-diene, isopimara-8,15-diene, sandaracopimaradiene Oryza sativa Japonica Group ?
-
 ?
sandaracopimaradiene + 3 [reduced NADPH-hemoprotein reductase] + 3 O2
-
 Arabidopsis thaliana 3beta-hydroxysandaracopimaradiene + 2alpha-hydroxysandaracopimaradiene + 3 [oxidized NADPH-hemoprotein reductase] + 4 H2O
-
 ?
sandaracopimaradiene + [reduced NADPH-hemoprotein reductase] + O2
-
 Arabidopsis thaliana ?
-
 ?
syn-aphidicolene + 3 [reduced NADPH-hemoprotein reductase] + 3 O2
-
 Arabidopsis thaliana 3beta-hydroxy-syn-aphidicolene + 2alpha-hydroxysandaracopimaradiene + 3 [oxidized NADPH-hemoprotein reductase] + 4 H2O
-
 ?
syn-aphidicolene + [reduced NADPH-hemoprotein reductase] + O2
-
 Arabidopsis thaliana ?
-
 ?
syn-labdatriene + [reduced NADPH-hemoprotein reductase] + O2
-
 Arabidopsis thaliana ?
-
 ?
syn-pimara-7,15-diene + 3 [reduced NADPH-hemoprotein reductase] + 3 O2
-
 Arabidopsis thaliana 3beta-hydroxy-syn-pimaradiene + 2alpha-hydroxy-syn-pimaradiene + 3 [oxidized NADPH-hemoprotein reductase] + 4 H2O
-
 ?
syn-pimara-7,15-diene + [reduced NADPH-hemoprotein reductase] + O2
-
 Arabidopsis thaliana ?
-
 ?
syn-pimara-9(11),15-diene + [reduced NADPH-hemoprotein reductase] + O2 low activity Arabidopsis thaliana ?
-
 ?
syn-stemarene + [reduced NADPH-hemoprotein reductase] + O2
-
 Arabidopsis thaliana ?
-
 ?
syn-stemodene + [reduced NADPH-hemoprotein reductase] + O2
-
 Arabidopsis thaliana ?
-
 ?

Synonyms

Synonyms Comment Organism
AtKO
-
 Arabidopsis thaliana
CYP701A6
-
 Oryza sativa Japonica Group
ent-kaurene oxidase 2
-
 Oryza sativa Japonica Group
KO2
-
 Arabidopsis thaliana
KO2
-
 Oryza sativa Japonica Group
OsKO2
-
 Oryza sativa Japonica Group

Cofactor

Cofactor Comment Organism Structure
cytochrome P450
-
 Arabidopsis thaliana
cytochrome P450
-
 Oryza sativa Japonica Group
NADPH
-
 Arabidopsis thaliana
NADPH
-
 Oryza sativa Japonica Group

General Information

General Information Comment Organism
additional information a modular metabolic engineering system is used in a combinatorial biosynthetic approach to detect substrates of ent-kaurene oxidase, overview Arabidopsis thaliana
additional information a modular metabolic engineering system is used in a combinatorial biosynthetic approach to detect substrates of ent-kaurene oxidase, overview Oryza sativa Japonica Group
physiological function the multiply reactive cytochrome P450, ent-kaurene oxidase (KO), is involved in production of the diterpenoid plant hormone gibberellin Arabidopsis thaliana
physiological function the multiply reactive cytochrome P450, ent-kaurene oxidase (KO), is involved in production of the diterpenoid plant hormone gibberellin Oryza sativa Japonica Group