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Recombinant Whole‐Cell Mediated Baeyer–Villiger Oxidation of Perhydropyran‐Type Ketones
Author(s) -
Mihovilovic Marko D.,
Grötzl Birgit,
Kandioller Wolfgang,
Muskotál Adél,
Snajdrova Radka,
Rudroff Florian,
Spreitzer Helmut
Publication year - 2008
Publication title -
chemistry and biodiversity
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.427
H-Index - 70
eISSN - 1612-1880
pISSN - 1612-1872
DOI - 10.1002/cbdv.200890048
Subject(s) - monooxygenase , chemistry , stereocenter , biotransformation , ketone , enzyme , substrate (aquarium) , chemoselectivity , stereochemistry , recombinant dna , biocatalysis , ring (chemistry) , escherichia coli , organic chemistry , biochemistry , enantioselective synthesis , catalysis , reaction mechanism , cytochrome p450 , gene , oceanography , geology
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.