Chemoselective screening for the reduction of a chiral functionalised (±)-2-(phenylthio)cyclohexanone by whole cells of Brazilian micro-organisms

Piovan, Leandro; Kagohara, Edna; Ricci, Luís C.; Keppler, Artur F.; Capelari, Marina; Andrade, Leandro H.; Comasseto, J. V.; Porto, André L. M.

doi:10.1016/j.tetasy.2008.10.003

Cited by 10 publications

(3 citation statements)

References 26 publications

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“…Even in the cases in which the enzyme engaged in the substrate conversion is well-established, its activity can be modified by other compounds present in the culture, and the desired product may be further metabolized. For instance, the prolonged oxidation of sulfides by toluene dioxygenase of Pseudomonas putida is accompanied by the partial reduction catalyzed by a specific reductase ( vide infra ). , A preliminary screening can be performed on model substrates prior to system application for the more demanding ones …”

Section: Biological Oxidationsmentioning

confidence: 99%

“…468,469 A preliminary screening can be performed on model substrates prior to system application for the more demanding ones. 470 Another problem in whole-cell biocatalysis is connected with a low reaction rate. The cell envelopes containing the enzyme are not quite easily penetrated by the substrate molecules, and this permeation barrier can limit the rate of the catalytic process.…”

Section: Whole-cell Systemsmentioning

confidence: 99%

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Enantioselective Synthesis of Sulfoxides: 2000−2009

2010

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Elz ˙bieta Wojaczyn ´ska (ne ´e Ostrycharz) was born in Z ˙migród, Poland. She received her M.Sc. degree in organic chemistry from Wrocław University of Technology in 1997. Her doctoral thesis on the enantioselective synthesis and application of chiral sulfoxides was completed under the supervision of Professor Jacek Skarz ˙ewski in 2001. Her research at the Department of Organic Chemistry of the Wrocław University of Technology focuses on the synthesis of new chiral building blocks and of novel chiral ligands for the asymmetric synthesis. Jacek Wojaczyn ´ski was born in Wrocław in 1969. He graduated from the University of Wrocław in inorganic chemistry in 1993. He received his Ph.D. in 1998 for work on the influence of asymmetric modification of the porphyrin periphery on the properties of formed complexes. He is a member of the Porphyrin Chemistry Research Group led by Professor Lechosław Latos-Graz ˙yn ´ski at the Department of Chemistry, University of Wrocław. His current scientific interests include degradation of tetrapyrrolic macrocycles and investigation of paramagnetic hemoproteins using NMR spectroscopy.

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Section: Biological Oxidationsmentioning

confidence: 99%

Section: Whole-cell Systemsmentioning

confidence: 99%

Enantioselective Synthesis of Sulfoxides: 2000−2009

2010

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“…In the 60-70s, Auret's group studied the fungal oxidation of diaryl and aryl alkyl sulfides employing mainly A. niger with certain success albeit the enantiomeric excesses (ee s ) and optical rotation signs resulted rather variable and substrate over-oxidation (sulfone formation) was always detected [14,[22][23][24]. More recently, it has been studied the possibility of performing sulfoxidations using A. terreus [25,26].…”

Section: Introductionmentioning

confidence: 99%

Aspergillus genus as a source of new catalysts for sulfide oxidation

Mascotti¹,

Orden²,

Bisogno³

et al. 2012

Journal of Molecular Catalysis B: Enzymatic

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Asymmetric synthesis of duloxetine intermediate (S)-(-)-3-N-methylamino-1-(2-thienyl)-1-propanol using immobilized Saccharomyces cerevisiae in liquid-core sodium alginate/chitosan/sodium alginate microcapsules

Haibing

Tang

et al. 2014

Bioprocess Biosyst Eng

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Duloxetine intermediate (S)-(-)-3-N-methylamino-1-(2-thienyl)-1-propanol was synthesized using ACA liquid-core immobilized Saccharomyces cerevisiae CGMCC No. 2230. The optimum culture time for ACA liquid-core immobilized cells was found to be 28 h. The optimum ACA liquid-core capsule formation conditions were found to be 90% chitosan deacetylation, 30,000-50,000 chitosan molecular weight, 5.0 g/L chitosan, and pH 6.0 citrate buffer solution. The highest activity was found when reduction conditions were pH 6.0, 30 °C and 180 rpm. The ACA-immobilized cells can be reused nine times and only 40% of the activity is retained after nine cycles. Product inhibition of reduction was observed in batch reduction. Continuous reduction in the membrane reactor was found to remove the product inhibition on reduction and improve production capacity. Conversion reached 100% and enantiometric excess of (S)-(-)-3-N-methylamino-1-(2-thienyl)-1-propanol exceeded 99.0% in continuous reduction of 5 g/L 3-N-methylamino-1-(2-thienyl)-1-propanone in the membrane reactor.

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Chemoselective screening for the reduction of a chiral functionalised (±)-2-(phenylthio)cyclohexanone by whole cells of Brazilian micro-organisms

Cited by 10 publications

References 26 publications

Enantioselective Synthesis of Sulfoxides: 2000−2009

Enantioselective Synthesis of Sulfoxides: 2000−2009

Aspergillus genus as a source of new catalysts for sulfide oxidation

Asymmetric synthesis of duloxetine intermediate (S)-(-)-3-N-methylamino-1-(2-thienyl)-1-propanol using immobilized Saccharomyces cerevisiae in liquid-core sodium alginate/chitosan/sodium alginate microcapsules

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