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Literature summary for 1.14.13.16 extracted from

  • Clouthier, C.M.; Kayser, M.M.
    Increasing the enantioselectivity of cyclopentanone monooxygenase (CPMO): profile of new CPMO mutants (2006), Tetrahedron Asymmetry, 17, 2649-2653.
No PubMed abstract available
Search for more literature for 1.14.13.16

Cloned(Commentary)

Cloned (Comment) Organism
overexpression of wild-type and mutant enzymes in Escherichia coli Acinetobacter sp.

Protein Variants

Protein Variants Comment Organism
F156H/G157L site-directed mutagenesis, the mutant shows altered substrate specificity and stereoselectivity compared to the wild-type enzyme Acinetobacter sp.
F156L/G157F site-directed mutagenesis, the mutations improve the hydrophobic active site pocket increasing enzyme selectivity and stereospecificity Acinetobacter sp.
F156N/G157Y site-directed mutagenesis, the mutant shows altered substrate specificity and stereoselectivity compared to the wild-type enzyme Acinetobacter sp.
F450C site-directed mutagenesis, the mutant shows altered substrate specificity and stereoselectivity compared to the wild-type enzyme Acinetobacter sp.
F450I site-directed mutagenesis, the mutant shows altered substrate specificity and stereoselectivity compared to the wild-type enzyme Acinetobacter sp.
G119S/F450Y site-directed mutagenesis, the mutant shows altered substrate specificity and stereoselectivity compared to the wild-type enzyme Acinetobacter sp.
additional information active site mutations to improve enantioselectivity of the enzyme towards 4-substituted cyclohexanone substrates, method evaluation, overview, the effect of mutation of residues 449 and 450 does not have a full impact on the improvement of the hydrophobic pocket Acinetobacter sp.

Natural Substrates/ Products (Substrates)

Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
cyclopentanone + NADPH + O2 Acinetobacter sp.
-
 5-valerolactone + NADP+ + H2O
-
 ?
cyclopentanone + NADPH + O2 Acinetobacter sp. NCIB 9871
-
 5-valerolactone + NADP+ + H2O
-
 ?

Organism

Organism UniProt Comment Textmining
Acinetobacter sp.
-
-
-
Acinetobacter sp. NCIB 9871
-
-
-

Reaction

Reaction Comment Organism Reaction ID
cyclopentanone + NADPH + H+ + O2 = 5-valerolactone + NADP+ + H2O residues Phe450 and Phe156 are important for reaction stereospecificity Acinetobacter sp.
a

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
4-acetoxy-cyclohexanone + NADPH + O2
-
 Acinetobacter sp. 4-acetoxy-hexano-6-lactone + NADP+ + H2O
-
 ?
4-acetoxy-cyclohexanone + NADPH + O2
-
 Acinetobacter sp. NCIB 9871 4-acetoxy-hexano-6-lactone + NADP+ + H2O
-
 ?
4-allyl-cyclohexanone + NADPH + O2
-
 Acinetobacter sp. 4-allyl-hexano-6-lactone + NADP+ + H2O
-
 ?
4-allyl-cyclohexanone + NADPH + O2
-
 Acinetobacter sp. NCIB 9871 4-allyl-hexano-6-lactone + NADP+ + H2O
-
 ?
4-ethoxy-cyclohexanone + NADPH + O2
-
 Acinetobacter sp. 4-ethoxy-hexano-6-lactone + NADP+ + H2O
-
 ?
4-ethyl-cyclohexanone + NADPH + O2
-
 Acinetobacter sp. 4-ethyl-hexano-6-lactone + NADP+ + H2O
-
 ?
4-hydroxy-4-allyl-cyclohexanone + NADPH + O2
-
 Acinetobacter sp. ?
-
 ?
4-hydroxy-4-ethyl-cyclohexanone + NADPH + O2
-
 Acinetobacter sp. ?
-
 ?
4-hydroxy-4-methyl-cyclohexanone + NADPH + O2
-
 Acinetobacter sp. ?
-
 ?
4-hydroxy-cyclohexanone + NADPH + O2
-
 Acinetobacter sp. 4-hydroxy-hexano-6-lactone + NADP+ + H2O
-
 ?
4-hydroxy-cyclohexanone + NADPH + O2
-
 Acinetobacter sp. NCIB 9871 4-hydroxy-hexano-6-lactone + NADP+ + H2O
-
 ?
4-methoxy-cyclohexanone + NADPH + O2
-
 Acinetobacter sp. 4-methoxy-hexano-6-lactone + NADP+ + H2O
-
 ?
4-methyl-cyclohexanone + NADPH + O2
-
 Acinetobacter sp. 4-methyl-hexano-6-lactone + NADP+ + H2O
-
 ?
4-n-propyl-cyclohexanone + NADPH + O2
-
 Acinetobacter sp. 4-n-propyl-hexano-6-lactone + NADP+ + H2O
-
 ?
cyclopentanone + NADPH + O2
-
 Acinetobacter sp. 5-valerolactone + NADP+ + H2O
-
 ?
cyclopentanone + NADPH + O2
-
 Acinetobacter sp. NCIB 9871 5-valerolactone + NADP+ + H2O
-
 ?
additional information the enzyme acts as Baeyer-Villiger monooxygenase, substrate specificity and enantioselectivity of wild-type and mutant enzymes, structure-function analysis and comparison to cyclohexanone monooxygenase, EC 1.14.13.22, residues Phe450 and Phe156 are important, overview Acinetobacter sp. ?
-
 ?
additional information the enzyme acts as Baeyer-Villiger monooxygenase, substrate specificity and enantioselectivity of wild-type and mutant enzymes, structure-function analysis and comparison to cyclohexanone monooxygenase, EC 1.14.13.22, residues Phe450 and Phe156 are important, overview Acinetobacter sp. NCIB 9871 ?
-
 ?

Synonyms

Synonyms Comment Organism
CPMO
-
 Acinetobacter sp.

Cofactor

Cofactor Comment Organism Structure
FAD bound Acinetobacter sp.
NADPH
-
 Acinetobacter sp.