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Literature summary extracted from

  • Doo, E.H.; Lee, W.H.; Seo, H.S.; Seo, J.H.; Park, J.B.
    Productivity of cyclohexanone oxidation of the recombinant Corynebacterium glutamicum expressing chnB of Acinetobacter calcoaceticus (2009), J. Biotechnol., 142, 164-169.
    View publication on PubMed

Application

EC Number Application Comment Organism
1.14.13.22 biotechnology biocatalysis system for Baeyer-Villiger oxidations, the average specific oxidation rate and product molar yield based on reaction substrate reaches 0.15 g/g dry cells/h (21.9 micromol/min/g of dry cells), at high cell densities (20 g dry cells/l) the specific product formation rate is lower with 0.12 g/g dry cells/h and 17.5 micromol/min/g of dry cells (probably due to low availability of the energy source glucose), though absolute yield is 2fold higher Acinetobacter calcoaceticus

Cloned(Commentary)

EC Number Cloned (Comment) Organism
1.14.13.22 PCR-amplification of chnB gene with template vector pMM4, cloning into pEKEx2 shuttle vector, expression in Corynebacterium glutamicum (ATCC13032) Acinetobacter calcoaceticus

Natural Substrates/ Products (Substrates)

EC Number Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
1.14.13.22 cyclohexanone + NADPH + H+ + O2 Acinetobacter calcoaceticus
-
 hexano-6-lactone + NADP+ + H2O
-
 ?
1.14.13.22 cyclohexanone + NADPH + H+ + O2 Acinetobacter calcoaceticus NCIMB 9871
-
 hexano-6-lactone + NADP+ + H2O
-
 ?

Organism

EC Number Organism UniProt Comment Textmining
1.14.13.22 Acinetobacter calcoaceticus
-
 NCIMB 9871
-
1.14.13.22 Acinetobacter calcoaceticus NCIMB 9871
-
 NCIMB 9871
-

Purification (Commentary)

EC Number Purification (Comment) Organism
1.14.13.22 cells centrifuged, washed with reaction buffer (0.1 M glycine/NaOH buffer, pH 9.0), disruption by ultrasonic processor, centrifugation, supernatants used as crude enzyme extracts Acinetobacter calcoaceticus

Specific Activity [micromol/min/mg]

EC Number Specific Activity Minimum [µmol/min/mg] Specific Activity Maximum [µmol/min/mg] Comment Organism
1.14.13.22 additional information
-
 activity below 0.1 micromol/min/mg protein, substrate cyclohexanone, induced (0.1 mM isopropylthiogalactoside) cell culture extracts, BHI medium or modified Riesenberg medium, 30°C Acinetobacter calcoaceticus
1.14.13.22 additional information
-
 whole cell activity to produce epsilon-caprolactone from cyclohexanone: initially 72 micromol/min/g dry cells, linearly falling to 14-18 micromol/min/g dry cells, sodium-potassium phosphate buffer, pH 7.0 with glucose (transferred from modified Riesenberg medium used for cultivation), 30°C Acinetobacter calcoaceticus
1.14.13.22 0.4
-
 substrate cyclohexanone, induced (1.0 mM isopropylthiogalactoside) cell culture extracts, modified Riesenberg medium, 30°C Acinetobacter calcoaceticus
1.14.13.22 0.5
-
 substrate cyclohexanone, induced (1.0 mM isopropylthiogalactoside) cell culture extracts, BHI medium, 30°C Acinetobacter calcoaceticus

Substrates and Products (Substrate)

EC Number Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
1.14.13.22 (2R,6S)-2,6-dimethylcyclohexanone + NADPH + O2 + H+
-
 Acinetobacter calcoaceticus (3R,7S)-3,7-dimethyloxepan-2-one + NADP+ + H2O 90% conversion at 20 h, 99% enantiomeric excess ?
1.14.13.22 (2R,6S)-2,6-dimethylcyclohexanone + NADPH + O2 + H+
-
 Acinetobacter calcoaceticus NCIMB 9871 (3R,7S)-3,7-dimethyloxepan-2-one + NADP+ + H2O 90% conversion at 20 h, 99% enantiomeric excess ?
1.14.13.22 (3R)-3-(1-methylethenyl)cyclohexanone + NADPH + O2 + H+
-
 Acinetobacter calcoaceticus (6S)-6-(1-methylethenyl)oxepan-2-one + NADP+ + H2O 99% regioselectivity ?
1.14.13.22 (3R)-3-(1-methylethenyl)cyclohexanone + NADPH + O2 + H+
-
 Acinetobacter calcoaceticus NCIMB 9871 (6S)-6-(1-methylethenyl)oxepan-2-one + NADP+ + H2O 99% regioselectivity ?
1.14.13.22 1,4-dioxaspiro[4.5]decan-8-one + NADPH + O2 + H+
-
 Acinetobacter calcoaceticus 1,4,8-trioxaspiro[4.6]undecan-9-one + NADP+ + H2O 80% conversion at 20 h ?
1.14.13.22 1,4-dioxaspiro[4.5]decan-8-one + NADPH + O2 + H+
-
 Acinetobacter calcoaceticus NCIMB 9871 1,4,8-trioxaspiro[4.6]undecan-9-one + NADP+ + H2O 80% conversion at 20 h ?
1.14.13.22 2,2,6-trimethylcyclohexanone + NADPH + O2 + H+
-
 Acinetobacter calcoaceticus 3,7,7-trimethyloxepan-2-one + NADP+ + H2O 66% conversion at 20 h ?
1.14.13.22 2,2,6-trimethylcyclohexanone + NADPH + O2 + H+
-
 Acinetobacter calcoaceticus NCIMB 9871 3,7,7-trimethyloxepan-2-one + NADP+ + H2O 66% conversion at 20 h ?
1.14.13.22 2-hexylcyclopentanone + NADPH + O2 + H+
-
 Acinetobacter calcoaceticus 6-hexyltetrahydro-2H-pyran-2-one + NADP+ + H2O 82% conversion at 20 h ?
1.14.13.22 2-methylcyclohexanone + NADPH + O2 + H+
-
 Acinetobacter calcoaceticus 7-methyloxepan-2-one + NADP+ + H2O
-
 ?
1.14.13.22 2-phenylcyclohexanone + NADPH + O2 + H+
-
 Acinetobacter calcoaceticus 7-phenyloxepan-2-one + NADP+ + H2O 51% conversion at 20 h ?
1.14.13.22 2-propylcyclohexanone + NADPH + O2 + H+
-
 Acinetobacter calcoaceticus (7S)-7-propyloxepan-2-one + NADP+ + H2O
-
 ?
1.14.13.22 3,3,5-trimethylcyclohexanone + NADPH + O2 + H+
-
 Acinetobacter calcoaceticus 4,6,6-trimethyloxepan-2-one + 4,4,6-trimethyloxepan-2-one + NADP+ + H2O 91% conversion at 20 h, 1/1 isomer with 98% enantiomeric excess ?
1.14.13.22 3,4-dihydronaphthalen-2(1H)-one + NADPH + O2 + H+
-
 Acinetobacter calcoaceticus 4,5-dihydro-3-benzoxepin-2(1H)-one + NADP+ + H2O more than 95% conversion one isomer ?
1.14.13.22 3-methylcyclohexanone + NADPH + O2 + H+
-
 Acinetobacter calcoaceticus (4S)-4-methyloxepan-2-one + (6R)-6-methyloxepan-2-one + NADP+ + H2O
-
 ?
1.14.13.22 4-ethylcyclohexanone + NADPH + O2 + H+
-
 Acinetobacter calcoaceticus (5S)-5-ethyloxepan-2-one + NADP+ + H2O 98% enantiomeric excess ?
1.14.13.22 4-methylcyclohexanone + NADPH + O2 + H+
-
 Acinetobacter calcoaceticus (5S)-5-methyloxepan-2-one + NADP+ + H2O 98% enantiomeric excess ?
1.14.13.22 4-tert-butylcyclohexanone + NADPH + O2 + H+
-
 Acinetobacter calcoaceticus (5S)-5-tert-butyloxepan-2-one + NADP+ + H2O 88% conversion at 20 h, 99% enantiomeric excess ?
1.14.13.22 cyclohexanone + NADPH + H+ + O2
-
 Acinetobacter calcoaceticus hexano-6-lactone + NADP+ + H2O
-
 ?
1.14.13.22 cyclohexanone + NADPH + H+ + O2
-
 Acinetobacter calcoaceticus NCIMB 9871 hexano-6-lactone + NADP+ + H2O
-
 ?
1.14.13.22 octahydronaphthalen-1(2H)-one + NADPH + O2 + H+
-
 Acinetobacter calcoaceticus octahydro-1-benzoxepin-2(3H)-one + octahydro-2-benzoxepin-1(3H)-one + NADP+ + H2O 100% conversion two isomers octahydro-1-benzoxepin-2(3H)-one + octahydro-2-benzoxepin-1(3H)-one with ratio 2/1 ?
1.14.13.22 octahydronaphthalen-2(1H)-one + NADPH + O2 + H+
-
 Acinetobacter calcoaceticus octahydro-3-benzoxepin-2(1H)-one + octahydro-2-benzoxepin-3(1H)-one + NADP+ + H2O 66% conversion at 20 h, octahydro-2-benzoxepin-3(1H)-one is the major product ?

Synonyms

EC Number Synonyms Comment Organism
1.14.13.22 CHMO
-
 Acinetobacter calcoaceticus
1.14.13.22 chnB protein
-
 Acinetobacter calcoaceticus
1.14.13.22 cyclohexanone monooxygenase
-
 Acinetobacter calcoaceticus