The analysis and application of a recombinant monooxygenase library as a biocatalyst for the Baeyer-Villiger reaction.
Because of their selectivity and catalytic efficiency, BVMOs are highly valuable biocatalysts for the chemoenzymatic synthesis of a broad range of useful compounds. In this study, we investigated the microbial Baeyer-Villiger oxidation and sulfoxidation of thioanisole and bicyclo[3.2.0]hept-2-en-6-one using whole Escherichia coli cells that recombined with each of the Baeyer-Villiger monooxygenases originated from Pseudomonas aeruginosa PAO1 and two from Streptomyces coelicolor A3(2). The three BVMOs were identified in the microbial genome database by a recently described protein sequence motif; e.g., BVMO motif (FXGXXXHXXXW). The reaction products were identified as (R)-/(S)sulfoxide and 2-oxabicyclo/3-oxabicyclo[3.3.0]oct-6-en-2-one by GC-MS analysis. Consequently, this study demonstrated that the three enzymes can indeed catalyze the Baeyer-Villiger reaction as a biocatalyst, and effective annotation tools can be efficiently exploited as a source of novel BVMOs.
Park
Jiyeoun
J
Korea Research Institute ofBioscience and Biotechnology, Daejeon 305-806, Korea.
Kim
Donghyun
D
Kim
Sujin
S
Kim
Jinhee
J
Bae
Kihwan
K
Lee
Choonghwan
C
D020816:Amino Acid Motifs; D000595:Amino Acid Sequence; D019086:Bridged Bicyclo Compounds, Heterocyclic / Q000737:chemistry; D002384:Catalysis; D003001:Cloning, Molecular; D030541:Databases, Genetic; D004926:Escherichia coli / Q000235:genetics; D015723:Gene Library; D016680:Genome, Bacterial; D007700:Kinetics; D006899:Mixed Function Oxygenases / Q000737:chemistry* / Q000235:genetics* / Q000378:metabolism; D008969:Molecular Sequence Data; D010084:Oxidation-Reduction; D011485:Protein Binding; D017434:Protein Structure, Tertiary; D011550:Pseudomonas aeruginosa / Q000201:enzymology; D011994:Recombinant Proteins / Q000737:chemistry / Q000378:metabolism; D015203:Reproducibility of Results; D017386:Sequence Homology, Amino Acid; D048372:Streptomyces coelicolor / Q000201:enzymology; D013379:Substrate Specificity; D013440:Sulfides / Q000737:chemistry* / Q000378:metabolism; D013696:Temperature
D019086:Bridged Bicyclo Compounds, Heterocyclic; D011994:Recombinant Proteins; D013440:Sulfides; C093850:methylphenylsulfide; D006899:Mixed Function Oxygenases