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Literature summary extracted from

  • Chen, X.; Zhang, C.; Too, H.
    Multienzyme biosynthesis of dihydroartemisinic acid (2017), Molecules, 22, 1422-1433 .
    View publication on PubMedView publication on EuropePMC

Application

EC Number Application Comment Organism
1.14.14.114 synthesis Saccharomyces cerevisiae expressing the native Artemisia annua cytochrome P450 monooxygenase (CYP71AV1) and artemisinic aldehyde D11(13) reductase (DBR2) is used as a whole-cell biocatalyst to produce the immediate artemisinin precursor, dihydroartemisinic acid (DHAA) Artemisia annua

Cloned(Commentary)

EC Number Cloned (Comment) Organism
1.14.14.114 gene cyp71av1, recombinant expression of cytochrome P450 CYP71AV1 in Saccharomyces cerevisiae, coexpression with artemisinic aldehyde D11(13) reductase (DBR2), and artemisinic aldehyde dehydrogenase (ALDH1), which recycles NADPH Artemisia annua

Protein Variants

EC Number Protein Variants Comment Organism
1.14.14.114 additional information Saccharomyces cerevisiae expressing the native Artemisia annua cytochrome P450 monooxygenase (CYP71AV1) and artemisinic aldehyde D11(13) reductase (DBR2) is used as a whole-cell biocatalyst to produce the immediate artemisinin precursor, dihydroartemisinic acid (DHAA). Introducing artemisinic aldehyde dehydrogenase (ALDH1) from Artemisia annua, which recycles NADPH, results in a significant enhancement in artemisinate titer. Method optimization and evaluation, host screening and cofactor engineering, overview. The co-expression of DBR2 and modulation of abiotic conditions result in a higher yield. Optimal condition are 80 OD yeast cells in 0.05 ml reaction at pH 8.0. Growing the yeast cells at 20°C in galactose medium increases the dihydroartemisinate titer by 50% Artemisia annua

Natural Substrates/ Products (Substrates)

EC Number Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
1.14.14.114 amorpha-4,11-diene + 3 O2 + [reduced NADPH-hemoprotein reductase] Artemisia annua overall reaction, multistep process artemisinate + [oxidized NADPH-hemoprotein reductase] + 4 H2O
-
 ?
1.14.14.114 amorpha-4,11-diene + O2 + [reduced NADPH-hemoprotein reductase] Artemisia annua
-
 artemisinic alcohol + [oxidized NADPH-hemoprotein reductase] + H2O
-
 ?
1.14.14.114 artemisinic alcohol + O2 + [reduced NADPH-hemoprotein reductase] Artemisia annua
-
 artemisinic aldehyde + [oxidized NADPH-hemoprotein reductase] + 2 H2O
-
 ?
1.14.14.114 artemisinic aldehyde + O2 + [reduced NADPH-hemoprotein reductase] Artemisia annua
-
 artemisinate + [oxidized NADPH-hemoprotein reductase] + H2O
-
 ?

Organism

EC Number Organism UniProt Comment Textmining
1.14.14.114 Artemisia annua Q1PS23
-
-

Substrates and Products (Substrate)

EC Number Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
1.14.14.114 amorpha-4,11-diene + 3 O2 + [reduced NADPH-hemoprotein reductase] overall reaction, multistep process Artemisia annua artemisinate + [oxidized NADPH-hemoprotein reductase] + 4 H2O
-
 ?
1.14.14.114 amorpha-4,11-diene + O2 + [reduced NADPH-hemoprotein reductase]
-
 Artemisia annua artemisinic alcohol + [oxidized NADPH-hemoprotein reductase] + H2O
-
 ?
1.14.14.114 artemisinic alcohol + O2 + [reduced NADPH-hemoprotein reductase]
-
 Artemisia annua artemisinic aldehyde + [oxidized NADPH-hemoprotein reductase] + 2 H2O
-
 ?
1.14.14.114 artemisinic aldehyde + O2 + [reduced NADPH-hemoprotein reductase]
-
 Artemisia annua artemisinate + [oxidized NADPH-hemoprotein reductase] + H2O
-
 ?

Synonyms

EC Number Synonyms Comment Organism
1.14.14.114 CYP71AV1
-
 Artemisia annua

pH Optimum

EC Number pH Optimum Minimum pH Optimum Maximum Comment Organism
1.14.14.114 8
-
 recombinant enzyme Artemisia annua

Cofactor

EC Number Cofactor Comment Organism Structure
1.14.14.114 cytochrome P450
-
 Artemisia annua
1.14.14.114 heme a heme catalytic site situated at the C-terminal domain Artemisia annua
1.14.14.114 NADPH-hemoprotein reductase A flavoprotein containing both FMN and FAD. This enzyme catalyses the transfer of electrons from NADPH, an obligatory two-electron donor, to microsomal P-450 monooxygenases, EC 1.14.14._ Artemisia annua

General Information

EC Number General Information Comment Organism
1.14.14.114 metabolism the first oxidation step by cytochrome P450 (CYP71AV1) is the main rate-limiting step in the dihydroartemisinic acid (DHAA) pathway Artemisia annua
1.14.14.114 physiological function enzyme CYP71AV1 is the critical enzyme that is capable of catalyzing three consecutive oxidation reactions at C-12 position of amorpha-4,11-diene to artemisinate. The heme catalytic site is situated at the C-terminal domain Artemisia annua