Resolution of fused bicyclic ketones by a recombinant biocatalyst expressing the Baeyer-Villiger monooxygenase gene Rv3049c from Mycobacterium tuberculosis H37Rv.
Recombinant Escherichia coli B834 (DE3) pDB5 expressing the Rv3049c gene encoding a Baeyer-Villiger monooxygenase from Mycobacterium tuberculosis H37Rv was used for regioselective oxidations of fused bicyclic ketones. This whole-cell system represents the first recombinant Baeyer-Villiger oxidation biocatalyst that effectively resolves the racemic starting materials in this series. Within biotransformations using this organism one substrate enantiomer remains in high optical purity, while the second enantiomer is oxidized to one type of regioisomeric lactone preferably.
Snajdrova
Radka
R
Vienna University of Technology, Institute of Applied Synthetic Chemistry, Getreidemarkt 9/163, A-1060, Vienna, Austria.
Grogan
Gideon
G
Mihovilovic
Marko D
MD
D001688:Biological Products / Q000737:chemistry; D001643:Bridged Bicyclo Compounds / Q000737:chemistry*; D002384:Catalysis; D004926:Escherichia coli / Q000201:enzymology / Q000235:genetics; D007659:Ketones / Q000737:chemistry* / Q000378:metabolism*; D007783:Lactones / Q000737:chemistry; D015394:Molecular Structure; D009169:Mycobacterium tuberculosis / Q000201:enzymology* / Q000235:genetics; D010084:Oxidation-Reduction; D010105:Oxygenases / Q000235:genetics / Q000378:metabolism*; D011994:Recombinant Proteins / Q000235:genetics / Q000378:metabolism*; D013379:Substrate Specificity
D001688:Biological Products; D001643:Bridged Bicyclo Compounds; D007659:Ketones; D007783:Lactones; D011994:Recombinant Proteins; D010105:Oxygenases