Biotransformation of α-Bromoacetophenones by the Marine Fungus Aspergillus sydowii

Rocha, Lenilson C.; Ferreira, Hercules V.; Pimenta, Eli F.; Berlinck, Roberto Gomes Souza; Rezende, Maria Olímpia de Oliveira; Landgraf, Maria Diva; Seleghim, Mirna Helena Regali; Sette, Lara Durães; Porto, André Luiz Meleiro

doi:10.1007/s10126-009-9241-y

Cited by 46 publications

(24 citation statements)

References 17 publications

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“…Of note, such a dehalogenation reaction took place at 37 • C also in the absence of yeast. Thus, the elimination reaction was found to be independent from the biocatalyst [41,42], different from the behavior of the other microorganisms [43].…”

Section: Screening Of Biocatalysts For the Stereoselective Reduction mentioning

confidence: 80%

Stereoselective Chemoenzymatic Synthesis of Optically Active Aryl-Substituted Oxygen-Containing Heterocycles

et al. 2017

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A two-step stereoselective chemoenzymatic synthesis of optically active α-aryl-substituted oxygen heterocycles was developed, exploiting a whole-cell mediated asymmetric reduction of α-, β-, and γ-chloroalkyl arylketones followed by a stereospecific cyclization of the corresponding chlorohydrins into the target heterocycles. Among the various whole cells screened (baker's yeast, Kluyveromyces marxianus CBS 6556, Saccharomyces cerevisiae CBS 7336, Lactobacillus reuteri DSM 20016), baker's yeast was the one providing the best yields and the highest enantiomeric ratios (up to 95:5 er) in the bioreduction of the above ketones. The obtained optically active chlorohydrins could be almost quantitatively cyclized in a basic medium into the corresponding α-aryl-substituted cyclic ethers without any erosion of their enantiomeric integrity. In this respect, valuable, chiral non-racemic functionalized oxygen containing heterocycles (e.g., (S)-styrene oxide, (S)-2-phenyloxetane, (S)-2-phenyltetrahydrofuran), amenable to be further elaborated on, can be smoothly and successfully generated from their prochiral precursors.

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Section: Screening Of Biocatalysts For the Stereoselective Reduction mentioning

confidence: 80%

Stereoselective Chemoenzymatic Synthesis of Optically Active Aryl-Substituted Oxygen-Containing Heterocycles

et al. 2017

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“…Aspergillus sydowii spreads widely in ocean water (Martins et al 2011;Rocha et al 2010). A. sydowii could be used for field biodegradation of organophosphate pesticides (Hasan 1999).…”

Section: Effect Of Initial Ph On Formaldehyde Degradationmentioning

confidence: 99%

Formaldehyde degradation by a newly isolated fungus Aspergillus sp. HUA

Song

et al. 2013

Int. J. Environ. Sci. Technol.

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Formaldehyde is widely used in chemical manufacturing industry and classified as a human carcinogen. Discharging wastewater containing formaldehyde without treatment can cause serious risk to the water environment. In this study, a formaldehyde-resistant fungal strain was isolated from sewerage of a furniture factory. Isolate strain was identified based on the morphological and phylogenetic analyses. Formaldehyde-degrading fungus was determined by characterizing the mycelia growth in culture media, formaldehyde-resistant, formaldehydedegrading efficiencies, and specific enzyme activity involved in formaldehyde removal. Isolate strain HUA was identified as a member of Aspergillus sydowii. The strain HUA showed a growth in the presence of formaldehyde up to 2,400 mg l -1 at an optimum temperature of 25°C and optimum pH of 7. The specific activity of formaldehyde dehydrogenase and formate dehydrogenase could reach up to 5.02 and 1.06 U mg -1 , respectively. It indicated that isolated formaldehyde-resistant A. sydowii HUA strain would be potential used for removing formaldehyde from industrial wastewater.

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“…Recently, we investigated the use of marine fungi to catalyze several types of biotransformations in xenobiotic compounds, as the asymmetric reduction of 2-chloroacetophenone (Rocha et al 2009) and biotransformation of 2-bromoacetophenones (Rocha et al 2010a). In addition, whole cells of the marine fungi (Aspergillus sydowii Gc12, Penicillium raistrickii Ce16, Penicillium miczynskii Gc5, Trichoderma sp.…”

Section: Introductionmentioning

confidence: 99%

Bioconversion of Iodoacetophenones by Marine Fungi

et al. 2012

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Nine marine fungi (Aspergillus sclerotiorum CBMAI 849, Aspergillus sydowii Ce19, Beauveria felina CBMAI 738, Mucor racemosus CBMAI 847, Penicillium citrinum CBMAI 1186, Penicillium miczynskii Ce16, P. miczynskii Gc5, Penicillium oxalicum CBMAI 1185, and Trichoderma sp. Gc1) catalyzed the asymmetric bioconversion of iodoacetophenones 1-3 to corresponding iodophenylethanols 6-8. All the marine fungi produced exclusively (S)-ortho-iodophenylethanol 6 and (S)-meta-iodophenylethanol 7 in accordance to the Prelog rule. B. felina CBMAI 738, P. miczynskii Gc5, P. oxalicum CBMAI 1185, and Trichoderma sp. Gc1 produced (R)-para-iodophenylethanol 8 as product anti-Prelog. The bioconversion of para-iodoacetophenone 3 with whole cells of P. oxalicum CBMAI 1185 showed competitive reduction-oxidation reactions.

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Biotransformation of α-Bromoacetophenones by the Marine Fungus Aspergillus sydowii

Cited by 46 publications

References 17 publications

Stereoselective Chemoenzymatic Synthesis of Optically Active Aryl-Substituted Oxygen-Containing Heterocycles

Stereoselective Chemoenzymatic Synthesis of Optically Active Aryl-Substituted Oxygen-Containing Heterocycles

Formaldehyde degradation by a newly isolated fungus Aspergillus sp. HUA

Bioconversion of Iodoacetophenones by Marine Fungi

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