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Literature summary extracted from

  • Seo, J.; Ryu, J.Y.; Han, J.; Ahn, J.H.; Sadowsky, M.J.; Hur, H.G.; Chong, Y.
    Amino acid substitutions in naphthalene dioxygenase from Pseudomonas sp. strain NCIB 9816-4 result in regio- and stereo-specific hydroxylation of flavanone and isoflavanone (2013), Appl. Microbiol. Biotechnol., 97, 693-704.
    View publication on PubMed

Crystallization (Commentary)

EC Number Crystallization (Comment) Organism
1.14.12.12 modeling of structure with naphthalene bound at the active site. The mononuclear iron is coordinated by amino acid residues His208, His213, and Asp362 and a dioxygen molecule is bound in a side-on fashion. The substrate, naphthalene, is found 2.7 to 3.0 A below the dioxygen molecule and is confined in a small substrate binding site which is surrounded by several hydrophobic residues. The amino acid residues with aromatic side chains, including Phe224, Phe202, Phe352, Trp358, and His295 form a small, but rigid, substrate binding site Pseudomonas sp.

Protein Variants

EC Number Protein Variants Comment Organism
1.14.12.12 F224A 6.8% of wild-type activity with substrate naphthalene Pseudomonas sp.
1.14.12.12 F224C 9.1% of wild-type activity with substrate naphthalene Pseudomonas sp.
1.14.12.12 F224D 85.2% of wild-type activity with substrate naphthalene Pseudomonas sp.
1.14.12.12 F224E 94.7% of wild-type activity with substrate naphthalene Pseudomonas sp.
1.14.12.12 F224G 2.1% of wild-type activity with substrate naphthalene Pseudomonas sp.
1.14.12.12 F224H 92% of wild-type activity with substrate naphthalene Pseudomonas sp.
1.14.12.12 F224I 41.9% of wild-type activity with substrate naphthalene Pseudomonas sp.
1.14.12.12 F224K 95.3% of wild-type activity with substrate naphthalene Pseudomonas sp.
1.14.12.12 F224L 92.58% of wild-type activity with substrate naphthalene Pseudomonas sp.
1.14.12.12 F224M 97.5% of wild-type activity with substrate naphthalene Pseudomonas sp.
1.14.12.12 F224N 94.7% of wild-type activity with substrate naphthalene Pseudomonas sp.
1.14.12.12 F224P 15.1% of wild-type activity with substrate naphthalene Pseudomonas sp.
1.14.12.12 F224Q 20.4% of wild-type activity with substrate naphthalene Pseudomonas sp.
1.14.12.12 F224R 0.7% of wild-type activity with substrate naphthalene Pseudomonas sp.
1.14.12.12 F224S 2% of wild-type activity with substrate naphthalene Pseudomonas sp.
1.14.12.12 F224T 4.9% of wild-type activity with substrate naphthalene Pseudomonas sp.
1.14.12.12 F224V 13.2% of wild-type activity with substrate naphthalene Pseudomonas sp.
1.14.12.12 F224W 91.8% of wild-type activity with substrate naphthalene Pseudomonas sp.
1.14.12.12 F224Y 97% of wild-type activity with substrate naphthalene Pseudomonas sp.

Organism

EC Number Organism UniProt Comment Textmining
1.14.12.12 Pseudomonas sp.
-
-
-
1.14.12.12 Pseudomonas sp. NCIB 9816-4
-
-
-

Substrates and Products (Substrate)

EC Number Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
1.14.12.12 (2S)-flavanone + NADH + H+ + O2 no substrate for wild-type, substrate for mutants F224C, F224K, F224Q, F224Y Pseudomonas sp. 8-hydroxy-(2S)-flavanone + NAD+ + ? product has an oxygen atom directly attached to the aromatic ring. Upon completion of the dihydroxylation, the oxygen atom on the C-ring is believed to expel the 7-OH group through donation of its lone pair electrons and the charged intermediate. Once formed this readily re-aromatizes to provide 8-hydroxyflavanones or 8-hydroxyisoflavanones ?
1.14.12.12 (2S)-flavanone + NADH + H+ + O2 no substrate for wild-type, substrate for mutants F224C, F224K, F224Q, F224Y Pseudomonas sp. NCIB 9816-4 8-hydroxy-(2S)-flavanone + NAD+ + ? product has an oxygen atom directly attached to the aromatic ring. Upon completion of the dihydroxylation, the oxygen atom on the C-ring is believed to expel the 7-OH group through donation of its lone pair electrons and the charged intermediate. Once formed this readily re-aromatizes to provide 8-hydroxyflavanones or 8-hydroxyisoflavanones ?
1.14.12.12 (3S)-isoflavanone + NADH + H+ + O2 no substrate for wild-type, substrate for mutants F224K, F224Y Pseudomonas sp. 8-hydroxy-(3S)-isoflavanone + NAD+ + ? product has an oxygen atom directly attached to the aromatic ring. Upon completion of the dihydroxylation, the oxygen atom on the C-ring is believed to expel the 7-OH group through donation of its lone pair electrons and the charged intermediate. Once formed this readily re-aromatizes to provide 8-hydroxyflavanones or 8-hydroxyisoflavanones ?
1.14.12.12 (3S)-isoflavanone + NADH + H+ + O2 no substrate for wild-type, substrate for mutants F224K, F224Y Pseudomonas sp. NCIB 9816-4 8-hydroxy-(3S)-isoflavanone + NAD+ + ? product has an oxygen atom directly attached to the aromatic ring. Upon completion of the dihydroxylation, the oxygen atom on the C-ring is believed to expel the 7-OH group through donation of its lone pair electrons and the charged intermediate. Once formed this readily re-aromatizes to provide 8-hydroxyflavanones or 8-hydroxyisoflavanones ?
1.14.12.12 naphthalene + NADH + H+ + O2
-
 Pseudomonas sp. (1R,2S)-1,2-dihydronaphthalene-1,2-diol + NAD+
-
 ?
1.14.12.12 naphthalene + NADH + H+ + O2
-
 Pseudomonas sp. NCIB 9816-4 (1R,2S)-1,2-dihydronaphthalene-1,2-diol + NAD+
-
 ?