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Literature summary extracted from

  • Wriessnegger, T.; Augustin, P.; Engleder, M.; Leitner, E.; Mueller, M.; Kaluzna, I.; Schuermann, M.; Mink, D.; Zellnig, G.; Schwab, H.; Pichler, H.
    Production of the sesquiterpenoid (+)-nootkatone by metabolic engineering of Pichia pastoris (2014), Metab. Eng., 24, 18-29 .
    View publication on PubMed

Cloned(Commentary)

EC Number Cloned (Comment) Organism
1.14.14.151 co-expression of C-terminally FLAG-tagged premnaspirodiene oxygenase of Hyoscyamus muticus (HPO) and the Arabidopsis thaliana cytochrome P450 reductase (CPR) in Pichia pastoris strains ADH-C1 and -C3 Hyoscyamus muticus

Protein Variants

EC Number Protein Variants Comment Organism
1.14.14.151 additional information production of the sesquiterpenoid (+)-nootkatone by metabolic engineering of Pichia pastoris by generation of a strain co-expressing the premnaspirodiene oxygenase of Hyoscyamus muticus (HPO) and the Arabidopsis thaliana cytochrome P450 reductase (CPR) that hydroxylates extracellularly added (+)-valencene. Intracellular production of (+)-valencene by co-expression of valencene synthase from Callitropsis nootkatensis resolves the phase-transfer issues of (+)-valencene. Bi-phasic cultivations of Pichia pastoris result in the production of trans-nootkatol, which is oxidized to (+)-nootkatone by an intrinsic Pichia pastoris activity. Additional overexpression of a Pichia pastoris alcohol dehydrogenase and truncated hydroxy-methylglutaryl-CoA reductase (tHmg1p) significantly enhances the (+)-nootkatone yield to 208 mg/l cell culture in bioreactor cultivations. After 12 h of biotransformation about 50% of added (+)-valencene is converted to (+)-nootkatone without residual trans-nootkatol or ot herby-products, but with a moderate overall yield of 48% due to high substrate loss overtime. HPO,CPR and ADH-C3 protein levels are only marginally decreased by co-overexpression of tHMG1 Hyoscyamus muticus

Natural Substrates/ Products (Substrates)

EC Number Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
1.14.14.151 (+)-valencene + [reduced NADPH-hemoprotein reductase] + O2 Hyoscyamus muticus enzyme HPO-mediated biohydroxylation of (+)-valencene alpha-nootkatol + beta-nootkatol + [oxidized NADPH-hemoprotein reductase] + H2O
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 ?
1.14.14.151 additional information Hyoscyamus muticus co-expression of enzyme HPO and cytochrome P450 reductase (CPR) leads to the hydroxylation of externally added (+)-valencene to trans-nootkatol in Pichia pastoris cells ?
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 ?

Organism

EC Number Organism UniProt Comment Textmining
1.14.14.151 Hyoscyamus muticus A6YIH8
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-

Substrates and Products (Substrate)

EC Number Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
1.14.14.151 (+)-valencene + [reduced NADPH-hemoprotein reductase] + O2 enzyme HPO-mediated biohydroxylation of (+)-valencene Hyoscyamus muticus alpha-nootkatol + beta-nootkatol + [oxidized NADPH-hemoprotein reductase] + H2O
-
 ?
1.14.14.151 additional information co-expression of enzyme HPO and cytochrome P450 reductase (CPR) leads to the hydroxylation of externally added (+)-valencene to trans-nootkatol in Pichia pastoris cells Hyoscyamus muticus ?
-
 ?

Synonyms

EC Number Synonyms Comment Organism
1.14.14.151 CYP71D55 gene name, UniProt Hyoscyamus muticus
1.14.14.151 HPO
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 Hyoscyamus muticus

Cofactor

EC Number Cofactor Comment Organism Structure
1.14.14.151 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._ Hyoscyamus muticus