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Literature summary for 4.2.3.19 extracted from

  • Mafu, S.; Potter, K.C.; Hillwig, M.L.; Schulte, S.; Criswell, J.; Peters, R.J.
    Efficient heterocyclisation by (di)terpene synthases (2015), Chem. Commun. (Camb.), 51, 13485-13487 .
    View publication on PubMedView publication on EuropePMC
Search for more literature for 4.2.3.19

Cloned(Commentary)

Cloned (Comment) Organism
recombinant expression of enzyme mutant H212A in Escherichia coli Fusarium fujikuroi
recombinant expression of enzyme mutant H302A in Escherichia coli Physcomitrium patens

Protein Variants

Protein Variants Comment Organism
H212A the mutant shows altered substrate specificity compared to wild-type, the single histidine to alanine mutation converts FfCPS/KS into a bifunctional ent-13-epi-manoyl oxide synthase Fusarium fujikuroi
H302A the mutant efficiently produces ent-13-epi-manoyl oxide from geranylgeranyl diphosphate Physcomitrium patens
H302A the mutant shows altered substrate specificity compared to wild-type, the single histidine to alanine mutation converts PpCPS/KS into a bifunctional ent-13-epi-manoyl oxide synthase Physcomitrium patens

Natural Substrates/ Products (Substrates)

Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
ent-copalyl diphosphate Arabidopsis thaliana
-
 ent-kaurene + diphosphate
-
 ?
ent-copalyl diphosphate Oryza sativa
-
 ent-kaurene + diphosphate
-
 ?
ent-copalyl diphosphate Sinorhizobium fredii
-
 ent-kaurene + diphosphate
-
 ?
ent-copalyl diphosphate Physcomitrium patens
-
 ent-kaurene + diphosphate
-
 ?
ent-copalyl diphosphate Fusarium fujikuroi
-
 ent-kaurene + diphosphate
-
 ?
ent-copalyl diphosphate Fusarium fujikuroi CBS 195.34 / IMI 58289 / NRRL A-6831
-
 ent-kaurene + diphosphate
-
 ?

Organism

Organism UniProt Comment Textmining
Arabidopsis thaliana
-
-
-
Fusarium fujikuroi S0EA85 i.e. Gibberella fujikuroi
-
Fusarium fujikuroi CBS 195.34 / IMI 58289 / NRRL A-6831 S0EA85 i.e. Gibberella fujikuroi
-
Oryza sativa
-
-
-
Physcomitrium patens
-
-
-
Physcomitrium patens A5A8G0
-
-
Sinorhizobium fredii
-
-
-

Purification (Commentary)

Purification (Comment) Organism
recombinant enzyme mutant H212A from Escherichia coli Fusarium fujikuroi
recombinant enzyme mutant H302A from Escherichia coli Physcomitrium patens

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
8alpha-hydroxy-copalyl diphosphate produced by recombinant Arabidopsis thaliana ent-copalyl diphosphate synthase mutant H263A Physcomitrium patens ent-13-epi-manoyl oxide + diphosphate
-
 ?
8beta-hydroxy-ent-copalyl diphosphate
-
 Arabidopsis thaliana ent-13-epi-manoyl oxide + ent-kaurene + diphosphate
-
 ?
8beta-hydroxy-ent-copalyl diphosphate
-
 Oryza sativa ent-13-epi-manoyl oxide + ent-kaurene + diphosphate
-
 ?
ent-copalyl diphosphate
-
 Arabidopsis thaliana ent-kaurene + diphosphate
-
 ?
ent-copalyl diphosphate
-
 Oryza sativa ent-kaurene + diphosphate
-
 ?
ent-copalyl diphosphate
-
 Sinorhizobium fredii ent-kaurene + diphosphate
-
 ?
ent-copalyl diphosphate
-
 Physcomitrium patens ent-kaurene + diphosphate
-
 ?
ent-copalyl diphosphate
-
 Fusarium fujikuroi ent-kaurene + diphosphate
-
 ?
ent-copalyl diphosphate
-
 Fusarium fujikuroi CBS 195.34 / IMI 58289 / NRRL A-6831 ent-kaurene + diphosphate
-
 ?

Synonyms

Synonyms Comment Organism
bifunctional CPS/KS
-
 Physcomitrium patens
bifunctional CPS/KS
-
 Fusarium fujikuroi
copalyl diphosphate/kaurene synthase
-
 Physcomitrium patens
copalyl diphosphate/kaurene synthase
-
 Fusarium fujikuroi
FfCPS/KS
-
 Fusarium fujikuroi
PpCPS/KS
-
 Physcomitrium patens

General Information

General Information Comment Organism
evolution the enzyme is a class I diterpene cyclase Physcomitrium patens
evolution the enzyme is a class I diterpene cyclase Fusarium fujikuroi
additional information the production of manoyl oxide proceeds from a substrate wherein oxygen is already present in the form of a hydroxyl group added during bicyclization of the general diterpenoid precursor (E,E,E)-geranylgeranyl diphosphate (GGPP) to 8alpha-hydroxy-copalyl diphosphate catalysed by recombinant Arabidopsis thaliana ent-copalyl diphosphate synthase mutant H263A, EC 5.5.1.13. 8alpha-Hydroxy-copalyl diphosphate is then converted to ent-13-epi-manoyl oxide by the modified ent-kaurene synthase function of enzyme FfCPS/KS mutant H212A Fusarium fujikuroi
additional information the production of manoyl oxide proceeds from a substrate wherein oxygen is already present in the form of a hydroxyl group added during bicyclization of the general diterpenoid precursor (E,E,E)-geranylgeranyl diphosphate (GGPP) to 8alpha-hydroxy-copalyl diphosphate catalysed by recombinant Arabidopsis thaliana ent-copalyl diphosphate synthase mutant H263A, EC 5.5.1.13. 8alpha-Hydroxy-copalyl diphosphate is then converted to ent-13-epi-manoyl oxide by the modified ent-kaurene synthase function of enzyme PpCPS/KS mutant H302A Physcomitrium patens