A fluorescence-based assay for Baeyer-Villiger monooxygenases, hydroxylases and lactonases
Alkylation of umbelliferone and nitrophenol with chloroacetone, 3-chlorobutanone, 2-chlorocyclopentanone and 2-chlorocyclohexanone gave the corresponding 2-coumaryloxy and 2-nitrophenoxy ketones. The 2-coumaryloxy ketones were used as fluorogenic substrates to detect Baeyer-Villiger monooxygenases activities of microbial cultures in highthroughput using microtiter plates. The 2-coumaryloxy ketones were oxidized by microorganisms producing Baeyer-Villiger monooxygenases (BVMO), releasing umbelliferone as a fluorescent signal. The substrates were also biotransformed by a microbial monooxygenase (Trichosporon cutaneum). Chemical Baeyer-Villiger oxidation of 2-coumaryloxy ketones using meta-chloroperbenzoic acid proceeded regioselectively to the corresponding acyloxyalkyl derivatives of umbelliferone and nitrophenol. These chiral lactones underwent a fluorogenic and chromogenic reaction upon hydrolysis by esterases, in particular pig liver esterase. Enantioselectivity of the ester hydrolysis reaction was determined by chiral-phase analysis of the unreacted lactones.
Sicard, Renaud,Chen, Lu S.,Marsaioli, Anita J.,Reymond, Jean-Louis
p. 1041 - 1050
(2007/10/03)
Methyl derivatives of tetrahydrobenzo- and benzofurocoumarins, a new class of potential photoreagents toward DNA
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Rodighiero,Palumbo,Magno,et al.
p. 1405 - 1410
(2007/10/02)
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