A fluorescence-based assay for Baeyer-Villiger monooxygenases, hydroxylases and lactonases

dc.creatorSicard, R
dc.creatorChen, LS
dc.creatorMarsaioli, AJ
dc.creatorReymond, JL
dc.date2005
dc.dateJUN
dc.date2014-11-19T13:07:01Z
dc.date2015-11-26T18:03:19Z
dc.date2014-11-19T13:07:01Z
dc.date2015-11-26T18:03:19Z
dc.date.accessioned2018-03-29T00:45:10Z
dc.date.available2018-03-29T00:45:10Z
dc.identifierAdvanced Synthesis & Catalysis. Wiley-blackwell, v. 347, n. 41858, n. 1041, n. 1050, 2005.
dc.identifier1615-4150
dc.identifierWOS:000229760500019
dc.identifier10.1002/adsc.200505040
dc.identifierhttp://www.repositorio.unicamp.br/jspui/handle/REPOSIP/53190
dc.identifierhttp://www.repositorio.unicamp.br/handle/REPOSIP/53190
dc.identifierhttp://repositorio.unicamp.br/jspui/handle/REPOSIP/53190
dc.identifier.urihttp://repositorioslatinoamericanos.uchile.cl/handle/2250/1292498
dc.descriptionAlkylation of umbelliferone and nitrophenol with chloroacetone, 3-chlorobutanone, 2-chlorocyclopentanone and 2-chlorocyclohexanone gave the corresponding 2-coumaryloxy and 2-nitrophenoxy ketones. The 2-coumarytoxy ketones were used as fluorogenic substrates to detect Baeyer-Villiger monooxygenases activities of microbial cultures in high-throughput 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.
dc.description347
dc.description41858
dc.description1041
dc.description1050
dc.languageen
dc.publisherWiley-blackwell
dc.publisherMalden
dc.publisherEUA
dc.relationAdvanced Synthesis & Catalysis
dc.relationAdv. Synth. Catal.
dc.rightsfechado
dc.rightshttp://olabout.wiley.com/WileyCDA/Section/id-406071.html
dc.sourceWeb of Science
dc.subjectbiotransformations
dc.subjectenzyme catalysis
dc.subjectfluorescent probes
dc.subjectlactones
dc.subjectoxidation
dc.subjectChromogenic Substrate Arrays
dc.subjectFluorogenic Assay
dc.subjectEnzyme Assays
dc.subjectCatalytic Antibodies
dc.subjectDirected Evolution
dc.subjectIn-vitro
dc.subjectEsterases
dc.subjectLipases
dc.subjectFingerprints
dc.subjectUmbelliferone
dc.titleA fluorescence-based assay for Baeyer-Villiger monooxygenases, hydroxylases and lactonases
dc.typeArtículos de revistas


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