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Literature summary extracted from

  • Frey, M.; Schmauder, K.; Pateraki, I.; Spring, O.
    Biosynthesis of eupatolide-A metabolic route for sesquiterpene lactone formation involving the P450 enzyme CYP71DD6 (2018), ACS Chem. Biol., 13, 1536-1543 .
    View publication on PubMed

Cloned(Commentary)

EC Number Cloned (Comment) Organism
1.14.14.168 coexpression of HaG8H with the enzyme combination HaGAS1 + HaGAO in Nicotiana benthamiana leaves results in the formation of the lactonized version inunolide Helianthus annuus

Natural Substrates/ Products (Substrates)

EC Number Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
1.14.14.168 germacra-1(10),4,11(13)-trien-12-oate + [reduced NADPH-hemoprotein reductase] + O2 Helianthus annuus
-
 8beta-hydroxygermacra-1(10),4,11(13)-trien-12-oate + [oxidized NADPH-hemoprotein reductase] + H2O
-
 ?
1.14.14.169 8beta-hydroxygermacra-1(10),4,11(13)-trien-12-oate + [reduced NADPH-hemoprotein reductase] + O2 Helianthus annuus overall reaction. The product 6alpha,8beta-dihydroxygermacra-1(10),4,11(13)-trien-12-oate spontaneously lactonizes to eupatolide eupatolide + [oxidized NADPH-hemoprotein reductase] + 2 H2O
-
 ?

Organism

EC Number Organism UniProt Comment Textmining
1.14.14.168 Helianthus annuus F8S1H3
-
-
1.14.14.169 Helianthus annuus
-
-
-

Substrates and Products (Substrate)

EC Number Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
1.14.14.168 germacra-1(10),4,11(13)-trien-12-oate + [reduced NADPH-hemoprotein reductase] + O2
-
 Helianthus annuus 8beta-hydroxygermacra-1(10),4,11(13)-trien-12-oate + [oxidized NADPH-hemoprotein reductase] + H2O
-
 ?
1.14.14.168 germacra-1(10),4,11(13)-trien-12-oate + [reduced NADPH-hemoprotein reductase] + O2 germacra-1(10),4,11(13)-trien-12-oate i.e. germacrene A acid Helianthus annuus 8beta-hydroxygermacra-1(10),4,11(13)-trien-12-oate + [oxidized NADPH-hemoprotein reductase] + H2O
-
 ?
1.14.14.169 8beta-hydroxygermacra-1(10),4,11(13)-trien-12-oate + [reduced NADPH-hemoprotein reductase] + O2 overall reaction. The product 6alpha,8beta-dihydroxygermacra-1(10),4,11(13)-trien-12-oate spontaneously lactonizes to eupatolide Helianthus annuus eupatolide + [oxidized NADPH-hemoprotein reductase] + 2 H2O
-
 ?
1.14.14.169 8beta-hydroxygermacra-1(10),4,11(13)-trien-12-oate + [reduced NADPH-hemoprotein reductase] + O2 6alpha,8beta-dihydroxygermacra-1(10),4,11(13)-trien-12-oate spontaneously lactonizes to eupatolide Helianthus annuus 6alpha,8beta-dihydroxygermacra-1(10),4,11(13)-trien-12-oate + [oxidized NADPH-hemoprotein reductase] + H2O
-
 ?

Synonyms

EC Number Synonyms Comment Organism
1.14.14.168 CYP71BL1
-
 Helianthus annuus
1.14.14.168 GAA 8beta-hydroxylase
-
 Helianthus annuus
1.14.14.168 HaG8H
-
 Helianthus annuus
1.14.14.169 CYP71DD6
-
 Helianthus annuus
1.14.14.169 HaES
-
 Helianthus annuus

Cofactor

EC Number Cofactor Comment Organism Structure
1.14.14.168 cytochrome P-450 heme-thiolate protein Helianthus annuus
1.14.14.169 cytochrome P-450 heme-thiolate protein Helianthus annuus