1.14.13.84: 4-hydroxyacetophenone monooxygenase

This is an abbreviated version!
For detailed information about 4-hydroxyacetophenone monooxygenase, go to the full flat file.

Word Map on EC 1.14.13.84

1.14.13.84

baeyer-villiger

fluorescens

ketones

bvmos

acetophenones

cyclohexanone

nadph-dependent

biocatalytic

putida

enantioselectivity

resin

base-catalysed

stabilised

ring-substituted

characterise

fad

flavoproteins

synthesis

4-fluorophenol

fluorophenyl

fluoride

flavin-containing

synthons

4-fluorocatechol

sulfides

lactones

fluorinated

noncovalent

Reaction

Synonyms

4-hydroxyacetophenone monooxygenase, arylketone monooxygenase, Baeyer-Villiger monooxygenase, hAPA, HAPMO, More, oxygenase, 4-hydroxyacetophenone mono-

ECTree

1 Oxidoreductases

1.14 Acting on paired donors, with incorporation or reduction of molecular oxygen

1.14.13 With NADH or NADPH as one donor, and incorporation of one atom of oxygen into the other donor

1.14.13.84 4-hydroxyacetophenone monooxygenase

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Results	in table
1	Activating Compound
951	AA Sequence
8	Application
1	CAS Registry Number
10	Cloned(Commentary)
24	Cofactor
2	General Information
1	General Stability
5	Inhibitors
22	kcat/KM [mM/s]
75	KM Value [mM]
2	Localization
10	Molecular Weight [Da]
19	Natural Substrates/ Products (Substrates)
98	Organism
4	Pathway
10	pH Optimum
2	pH Range
19	Protein Variants
7	Purification (Commentary)
7	Reaction
9	Reaction Type
24	Reference
5	Specific Activity [micromol/min/mg]
219	Substrates and Products (Substrate)
13	Subunits
34	Synonyms
1	Systematic Name
6	Temperature Optimum [°C]
1	Temperature Stability [°C]
70	Turnover Number [1/s]

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Reference on EC 1.14.13.84 - 4-hydroxyacetophenone monooxygenase

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644553

Kamerbeek, N.M.; Moonen, M.J.; van der Ven, J.G.; van Berkel, W.J.H.; Fraaije, M.W.; Janssen, D.B.

4- Hydroxyacetophenone monooxygenase from Pseudomonas fluorescens ACB: a novel flavoprotein catalyzing Baeyer-Villiger oxidation of aromatic compounds

Eur. J. Biochem.

268

2547-2557

2001

Pseudomonas fluorescens, Pseudomonas fluorescens (Q93TJ5), Pseudomonas fluorescens ACB, Pseudomonas fluorescens ACB (Q93TJ5)

11322873

649387

Kamerbeek, N.M.; Olsthoorn, A.J.J.; Fraaije, M.W.; Janssen, D.B.

Substrate specificity and enantioselectivity of 4-hydroxyacetophenone monooxygenase

Appl. Environ. Microbiol.

419-426

2003

Pseudomonas fluorescens, Pseudomonas fluorescens ACB

12514023

651172

Kamerbeek, N.M.; Fraaije, M.W.; Janssen, D.B.

Identifying determinants of NADPH specificity in Baeyer-Villiger monooxygenases

Eur. J. Biochem.

271

2107-2116

2004

Pseudomonas fluorescens, Pseudomonas fluorescens ACB

15153101

651670

Tanner, A.; Hopper, D.J.

Conversion of 4-hydroxyacetophenone into 4-phenyl acetate by a flavin adenine dinucleotide-containing Baeyer-Villiger-type monooxygenase

J. Bacteriol.

182

6565-6569

2000

Pseudomonas putida, Pseudomonas putida JD1

11073896

659744

Mihovilovic, M.D.; Kapitan, P.; Rydz, J.; Rudroff, F.; Ogink, F.H.; Fraaije, M.W.

Biooxidation of ketones with a cyclobutanone structural motif by recombinant whole-cells expressing 4-hydroxyacetophenone monooxygenase

J. Mol. Catal. B

135-140

2005

Pseudomonas fluorescens, Pseudomonas fluorescens ACB

674475

van den Heuvel, R.H.; Tahallah, N.; Kamerbeek, N.M.; Fraaije, M.W.; van Berkel, W.J.; Janssen, D.B.; Heck, A.J.

Coenzyme binding during catalysis is beneficial for the stability of 4-hydroxyacetophenone monooxygenase

J. Biol. Chem.

280

32115-32121

2005

Pseudomonas fluorescens, Pseudomonas fluorescens ACB

16049018

677172

de Gonzalo, G.; Torres Pazmino, D.E.; Ottolina, G.; Fraaije, M.W.; Carrea, G.

4-Hydroxyacetophenone monooxygenase from Pseudomonas fluorescens ACB as an oxidative biocatalyst in the synthesis of optically active sulfoxides

Tetrahedron Asymmetry

130-135

2006

Pseudomonas fluorescens, Pseudomonas fluorescens ACB

687422

Moonen, M.J.; Kamerbeek, N.M.; Westphal, A.H.; Boeren, S.A.; Janssen, D.B.; Fraaije, M.W.; van Berkel, W.J.

Elucidation of the 4-hydroxyacetophenone catabolic pathway in Pseudomonas fluorescens ACB

J. Bacteriol.

190

5190-5198

2008

Pseudomonas fluorescens (Q93TJ5), Pseudomonas fluorescens, Pseudomonas fluorescens ACB (Q93TJ5), Pseudomonas fluorescens ACB

18502868

690108

Rodriguez, C.; De Gonzalo, G.; Fraaije, M.W.; Gotor, V.

Enzymatic kinetic resolution of racemic ketones catalyzed by Baeyer-Villiger monooxygenases

Tetrahedron Asymmetry

1338-1344

2007

Pseudomonas fluorescens

695775

Rehdorf, J.; Zimmer, C.L.; Bornscheuer, U.T.

Cloning, expression, characterization, and biocatalytic investigation of the 4-hydroxyacetophenone monooxygenase from Pseudomonas putida JD1

Appl. Environ. Microbiol.

3106-3114

2009

Pseudomonas putida (B7T912), Pseudomonas putida JD1 (B7T912), Pseudomonas putida JD1

19251889

697753

Rioz-Martinez, A.; De Gonzal, D.G.; Torres Pazmino, D.; Fraaije, M.; Gotor, V.

Enzymatic Baeyer-Villiger oxidation of Benzo-Fused ketones: Formation of regiocomplementary lactones

Eur. J. Org. Chem.

2526-2532

2009

Pseudomonas fluorescens (Q93TJ5), Pseudomonas fluorescens ACB (Q93TJ5)

697754

Rioz-Martinez, A.; De Gonzal, D.G.; Torres Pazmino, D.; Fraaije, M.; Gotor, V.

Enzymatic Baeyer-Villiger oxidation of benzo-fused ketones: Formation of regiocomplementary lactones

Eur. J. Org. Chem.

2009

2526-2532

2009

Pseudomonas fluorescens

712834

Rioz-Martinez, A.; de Gonzalo, G.; Torres Pazmino, D.E.; Fraaije, M.W.; Gotor, V.

Synthesis of chiral 3-alkyl-3,4-dihydroisocoumarins by dynamic kinetic resolutions catalyzed by a Baeyer-Villiger monooxygenase

J. Org. Chem.

2073-2076

2010

Pseudomonas fluorescens, Pseudomonas fluorescens ACB

20166716