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Literature summary for 1.14.14.1 extracted from

  • Roiban, G.; Agudo, R.; Ilie, A.; Lonsdale, R.; Reetz, M.
    CH-activating oxidative hydroxylation of 1-tetralones and related compounds with high regio- and stereoselectivity (2014), Chem. Commun. (Camb.), 50, 14310-14313 .
    View publication on PubMed
Search for more literature for 1.14.14.1

Application

Application Comment Organism
synthesis P450-BM3 enzyme mutants are ueful for CH-activating oxidative hydroxylation of readily available 1-tetralone derivatives with high degrees of regio- and stereoselectivity, e.g. oxidative hydroxylation of indane and tetralin, an approach which is currently not possible using chiral synthetic CH-activating transition metal catalysts Priestia megaterium

Protein Variants

Protein Variants Comment Organism
A328F site-directed mutagenesis, the mutant shows altered enantioselectivity compared to the wild-type enzyme Priestia megaterium
A328K site-directed mutagenesis, the mutant shows altered enantioselectivity compared to the wild-type enzyme Priestia megaterium
A328R site-directed mutagenesis, the mutant shows altered enantioselectivity compared to the wild-type enzyme Priestia megaterium
A328Y site-directed mutagenesis, the mutant shows altered enantioselectivity compared to the wild-type enzyme Priestia megaterium
additional information mutants of enzyme P450-BM3 evolved by directed evolution are excellent catalysts in the CH-activating oxidative hydroxylation of 1-tetralone derivatives and of indanone, with unusually high regio- and enantioselectivity Priestia megaterium

Natural Substrates/ Products (Substrates)

Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
indane + [reduced NADPH-hemoprotein reductase] + O2 Priestia megaterium
-
 (S)-3-hydroxy-indane + [oxidized NADPH-hemoprotein reductase] + H2O
-
 ?
indane + [reduced NADPH-hemoprotein reductase] + O2 Priestia megaterium ATCC 14581
-
 (S)-3-hydroxy-indane + [oxidized NADPH-hemoprotein reductase] + H2O
-
 ?
tetralin + [reduced NADPH-hemoprotein reductase] + O2 Priestia megaterium
-
 (S)-4-hydroxy-tetralin + [oxidized NADPH-hemoprotein reductase] + H2O
-
 ?
tetralin + [reduced NADPH-hemoprotein reductase] + O2 Priestia megaterium ATCC 14581
-
 (S)-4-hydroxy-tetralin + [oxidized NADPH-hemoprotein reductase] + H2O
-
 ?

Organism

Organism UniProt Comment Textmining
Priestia megaterium P14779
-
-
Priestia megaterium ATCC 14581 P14779
-
-

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
1-indanone + [reduced NADPH-hemoprotein reductase] + O2
-
 Priestia megaterium (S)-3-hydroxy-1-indanone + [oxidized NADPH-hemoprotein reductase] + H2O
-
 ?
1-indanone + [reduced NADPH-hemoprotein reductase] + O2
-
 Priestia megaterium ATCC 14581 (S)-3-hydroxy-1-indanone + [oxidized NADPH-hemoprotein reductase] + H2O
-
 ?
1-tetralone + [reduced NADPH-hemoprotein reductase] + O2
-
 Priestia megaterium (S)-4-hydroxy-1-tetralone + [oxidized NADPH-hemoprotein reductase] + H2O
-
 ?
1-tetralone + [reduced NADPH-hemoprotein reductase] + O2
-
 Priestia megaterium ATCC 14581 (S)-4-hydroxy-1-tetralone + [oxidized NADPH-hemoprotein reductase] + H2O
-
 ?
6-methoxy-1-tetralone + [reduced NADPH-hemoprotein reductase] + O2
-
 Priestia megaterium (S)-4-hydroxy-6-methoxy-1-tetralone + [oxidized NADPH-hemoprotein reductase] + H2O
-
 ?
7-methoxy-1-tetralone + [reduced NADPH-hemoprotein reductase] + O2
-
 Priestia megaterium (S)-4-hydroxy-7-methoxy-1-tetralone + [oxidized NADPH-hemoprotein reductase] + H2O
-
 ?
7-methoxy-1-tetralone + [reduced NADPH-hemoprotein reductase] + O2
-
 Priestia megaterium ATCC 14581 (S)-4-hydroxy-7-methoxy-1-tetralone + [oxidized NADPH-hemoprotein reductase] + H2O
-
 ?
indane + [reduced NADPH-hemoprotein reductase] + O2
-
 Priestia megaterium (S)-3-hydroxy-indane + [oxidized NADPH-hemoprotein reductase] + H2O
-
 ?
indane + [reduced NADPH-hemoprotein reductase] + O2
-
 Priestia megaterium ATCC 14581 (S)-3-hydroxy-indane + [oxidized NADPH-hemoprotein reductase] + H2O
-
 ?
tetralin + [reduced NADPH-hemoprotein reductase] + O2
-
 Priestia megaterium (S)-4-hydroxy-tetralin + [oxidized NADPH-hemoprotein reductase] + H2O
-
 ?
tetralin + [reduced NADPH-hemoprotein reductase] + O2
-
 Priestia megaterium ATCC 14581 (S)-4-hydroxy-tetralin + [oxidized NADPH-hemoprotein reductase] + H2O
-
 ?

Synonyms

Synonyms Comment Organism
BG04_163
-
 Priestia megaterium
CYP102A1
-
 Priestia megaterium
P450-BM3
-
 Priestia megaterium

Cofactor

Cofactor Comment Organism Structure
NADPH
-
 Priestia megaterium