title: Recombinant whole-cell mediated baeyer-villiger oxidation of perhydropyran-type ketones.
abstract: Recombinant Escherichia coli cells expressing eight Baeyer-Villiger monooxygenases of bacterial origin have been utilized to oxidize prochiral heterocyclic ketones containing a pyran ring system. Within the biotransformation, two stereogenic centers were introduced with high control of enantioselectivity. The chemoselectivity of the enzymatic reaction was found to be high in favor of the Baeyer-Villiger process when using substituted ketone precursors incorporating functional groups labile to oxidation. A significantly different behavior was observed for two groups of monooxygenases with respect to substrate acceptance, which is consistent with our previous classification into two enzyme clusters.
authors: Vienna University of Technology, Institute of Applied Synthetic Chemistry, Getreidemarkt 9/163-OC, A-1060 Vienna. mmihovil@pop.tuwien.ac.at
authors: Marko D
authors: MD
authors: Mihovilovic
authors: Birgit
authors: B
authors: Grötzl
authors: Wolfgang
authors: W
authors: Kandioller
authors: Adél
authors: A
authors: Muskotál
authors: Radka
authors: R
authors: Snajdrova
authors: Florian
authors: F
authors: Rudroff
authors: Helmut
authors: H
authors: Spreitzer
mesh_terms: D001711:Biotransformation; D004926:Escherichia coli / Q000201:enzymology* / Q000235:genetics; D007659:Ketones / Q000737:chemistry / Q000378:metabolism*; D006899:Mixed Function Oxygenases / Q000737:chemistry / Q000235:genetics / Q000378:metabolism*; D015394:Molecular Structure; D010084:Oxidation-Reduction; D011714:Pyrans / Q000737:chemistry / Q000378:metabolism*; D011994:Recombinant Proteins / Q000737:chemistry / Q000235:genetics / Q000378:metabolism*; D013237:Stereoisomerism
chemical_list: D007659:Ketones; D011714:Pyrans; D011994:Recombinant Proteins; D006899:Mixed Function Oxygenases