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discounted EARLY registration ends Dec 31, 2014
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discounted EARLY registration ends Dec 31, 2014
Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
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MetaCyc Enzyme: epi-isozizaene 5-monooxygenase

Gene: SCO5223 Accession Number: G-10612 (MetaCyc)

Synonyms: SC7E4.20, CYP170A1, cytochrome P450 170A1

Species: Streptomyces coelicolor A3(2)

Summary:
The subunit structure of this enzyme has not been reported.

Recombinant, soluble, N-terminally his-tagged enzyme was expressed in Escherichia coli and purified to homogeneity. The purified protein showed a unique carbon monoxide difference spectrum with a maximum at ~440 nm rather than the usual cytochrome P450 difference absorption maximum at ~450 nm [Zhao08].

This enzyme belongs to the cytochrome P450 superfamily of heme-containing monooxygenases.

Map Position: [5,682,098 -> 5,683,483]

Molecular Weight of Polypeptide: 50.938 kD (from nucleotide sequence)

Unification Links: Entrez-gene:1100664 , Protein Model Portal:Q9K498 , String:100226.SCO5223 , UniProt:Q9K498

Relationship Links: InterPro:IN-FAMILY:IPR001128 , InterPro:IN-FAMILY:IPR002401 , PDB:Structure:3DBG , PDB:Structure:3EL3 , Pfam:IN-FAMILY:PF00067 , Prints:IN-FAMILY:PR00385 , Prints:IN-FAMILY:PR00463

Gene-Reaction Schematic: ?

Credits:
Created 23-Apr-2008 by Fulcher CA , SRI International


Enzymatic reaction of: (5R)-albaflavenol monooxygenase (epi-isozizaene 5-monooxygenase)

(5R)-albaflavenol + NADPH + oxygen + H+ <=> albaflavenone + NADP+ + 2 H2O

The reaction direction shown, that is, A + B ↔ C + D versus C + D ↔ A + B, is in accordance with the direction in which it was curated.

The reaction is favored in the direction shown.

In Pathways: albaflavenone biosynthesis

Summary:
This enzyme catalyzes a two-step allylic oxidation of (+)-epi-isozizaene to form the 5-keto derivative albaflavenone via an epimeric mixture of (5S)-albaflavenol and (5R)-albaflavenol intermediates. All four compounds were detected in extracts of Streptomyces coelicolor A3(2) by gas chromatography/mass spectrometry [Zhao08].

The enzyme was assayed in vitro by reconstituting the enzyme with Escherichia coli flavodoxin and flavodoxin reductase in buffer containing the (+)-epi-isozizaene substrate. The reaction was started by adding NADPH and an NADPH-regenerating system. In vitro products and in vivo products produced by wild-type Streptomyces coelicolor A3(2) and a SCO5223 knock out strain were identified by GC/MS [Zhao08].


Enzymatic reaction of: (5S)-albaflavenol monooxygenase (epi-isozizaene 5-monooxygenase)

(5S)-albaflavenol + NADPH + oxygen + H+ <=> albaflavenone + NADP+ + 2 H2O

The reaction direction shown, that is, A + B ↔ C + D versus C + D ↔ A + B, is in accordance with the direction in which it was curated.

The reaction is favored in the direction shown.

In Pathways: albaflavenone biosynthesis

Summary:
This enzyme catalyzes a two-step allylic oxidation of (+)-epi-isozizaene to form the 5-keto derivative albaflavenone via an epimeric mixture of (5S)-albaflavenol and (5R)-albaflavenol intermediates. All four compounds were detected in extracts of Streptomyces coelicolor A3(2) by gas chromatography/mass spectrometry [Zhao08].

The enzyme was assayed in vitro by reconstituting the enzyme with Escherichia coli flavodoxin and flavodoxin reductase in buffer containing the (+)-epi-isozizaene substrate. The reaction was started by adding NADPH and an NADPH-regenerating system. In vitro products and in vivo products produced by wild-type Streptomyces coelicolor A3(2) and a SCO5223 knock out strain were identified by GC/MS [Zhao08].


Enzymatic reaction of: (5R)-albaflavenol synthase (epi-isozizaene 5-monooxygenase)

(+)-epi-isozizaene + NADPH + oxygen + H+ <=> (5R)-albaflavenol + NADP+ + H2O

The reaction direction shown, that is, A + B ↔ C + D versus C + D ↔ A + B, is in accordance with the direction in which it was curated.

The reaction is favored in the direction shown.

In Pathways: albaflavenone biosynthesis

Summary:
This enzyme catalyzes a two-step allylic oxidation of (+)-epi-isozizaene to form the 5-keto derivative albaflavenone via an epimeric mixture of (5S)-albaflavenol and (5R)-albaflavenol intermediates. All four compounds were detected in extracts of Streptomyces coelicolor A3(2) by gas chromatography/mass spectrometry [Zhao08].

The enzyme was assayed in vitro by reconstituting the enzyme with Escherichia coli flavodoxin and flavodoxin reductase in buffer containing the (+)-epi-isozizaene substrate. The reaction was started by adding NADPH and an NADPH-regenerating system. In vitro products and in vivo products produced by wild-type Streptomyces coelicolor A3(2) and a SCO5223 knock out strain were identified by GC/MS [Zhao08].


Enzymatic reaction of: (5S)-albaflavenol synthase (epi-isozizaene 5-monooxygenase)

(+)-epi-isozizaene + NADPH + oxygen + H+ <=> (5S)-albaflavenol + NADP+ + H2O

The reaction direction shown, that is, A + B ↔ C + D versus C + D ↔ A + B, is in accordance with the direction in which it was curated.

The reaction is favored in the direction shown.

In Pathways: albaflavenone biosynthesis

Summary:
This enzyme catalyzes a two-step allylic oxidation of (+)-epi-isozizaene to form the 5-keto derivative albaflavenone via an epimeric mixture of (5S)-albaflavenol and (5R)-albaflavenol intermediates. All four compounds were detected in extracts of Streptomyces coelicolor A3(2) by gas chromatography/mass spectrometry [Zhao08].

The enzyme was assayed in vitro by reconstituting the enzyme with Escherichia coli flavodoxin and flavodoxin reductase in buffer containing the (+)-epi-isozizaene substrate. The reaction was started by adding NADPH and an NADPH-regenerating system. In vitro products and in vivo products produced by wild-type Streptomyces coelicolor A3(2) and a SCO5223 knock out strain were identified by GC/MS [Zhao08].


References

Zhao08: Zhao B, Lin X, Lei L, Lamb DC, Kelly SL, Waterman MR, Cane DE (2008). "Biosynthesis of the Sesquiterpene Antibiotic Albaflavenone in Streptomyces coelicolor A3(2)." J Biol Chem 283(13);8183-9. PMID: 18234666


Report Errors or Provide Feedback
Please cite the following article in publications resulting from the use of MetaCyc: Caspi et al, Nucleic Acids Research 42:D459-D471 2014
Page generated by SRI International Pathway Tools version 18.5 on Fri Nov 28, 2014, BIOCYC13B.