Enantioselective hydrolysis of 1-aryl ethyl acetates and reduction of aryl methyl ketones using carrot, celeriac and horseradish enzyme systems

Mączka, Wanda; Mironowicz, Agnieszka

doi:10.1016/s0957-4166(02)00635-3

Cited by 39 publications

(14 citation statements)

References 7 publications

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“…The Jerusalem artichoke oxidized racemic 1-phenylethanol and 1-(2-naphthyl)ethanol very stereoselectivly, yielding 58% of R-1-phenylethanol (ee = 80%) and 54% of R-1-(2-naphthyl)ethanol (ee = 95%) [12]. When comparing the oxidations of 1-and 2-naphthalene derivatives [8], the β-position was revealated to be more suitable for enzymatic reaction because, similarly to the Jerusalem artichoke, the celeriac enzymatic system transformed 1-(2-naphthyl)ethanol in 60% with a 35% enantiometic excess S-(-)-enantiomer of unreacted alcohol, but the other alcohol with biaryl ring, that is, 1-(1-naphthyl)ethanol, was not transformed.…”

Section: Oxidation Of Indan-1-ol Using the Plant Enzyme Systemmentioning

confidence: 99%

“…In the biological approaches using biocatalysts, optically active alcohols are prepared from prochiral ketones [8][9][10][11], or racemic alcohols as starting materials [8,[12][13][14][15]. Biocatalytic desymmetrization using ketones is highly significant in several processes, as this allows one to obtain pure enantiomer in a 100% theoretical yield.…”

Section: Introductionmentioning

confidence: 99%

“…Plant biocatalysts have been applied primarily in the reduction of ketones. [8][9][10][11][19][20][21][22][23][24][25]. Biooxidation of alcohols has been described much less [8,[12][13][14][15]22].…”

Section: Introductionmentioning

confidence: 99%

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Plant-Mediated Enantioselective Transformation of Indan-1-One and Indan-1-ol

et al. 2019

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The main purpose of this work was to discover the way to obtain pure enantiomers of indan-1-ol. The subject of the study was the ability of the plant enzyme system to reduce the carbonyl group of indan-1-one, as well as to oxidize the hydroxyl group of racemic indan-1-ol. Locally available fruit and vegetables were selected for stereoselective biotransformation. During the reduction, mainly alcohol of the S-(+)-configuration with a high enantiomeric excess (ee = 99%) was obtained. The opposite enantiomer was obtained in bioreduction with the apple and parsley. Racemic indan-1-ol was oxidized by all catalysts. The best result was obtained for the Jerusalem artichoke: Over 50% conversion was observed after 1 h, and the enantiomeric excess of unreacted R-(–)-indan1-ol was 100%.

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Section: Oxidation Of Indan-1-ol Using the Plant Enzyme Systemmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Plant-Mediated Enantioselective Transformation of Indan-1-One and Indan-1-ol

et al. 2019

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“…12,[23][24][25][26][27][28][29][30] To our knowledge, there is just one paper concerning the Daucus carota promoted bioreduction of two α-tetralones, namely the α-tetralone itself and the 6-methoxy-1-tetralone. 12 Therefore, we decided to investigate the behaviour of a series of substituted α-tetralones towards the bioreduction with Daucus carota, aiming higher yields (theoretically 100%) than those earlier obtained using CALB in the kinetic resolution (theoretically 50%).…”

Section: Introductionmentioning

confidence: 99%

Bioreduction of substituted a-tetralones promoted by Daucus carota root

Ferraz¹,

Bianco²,

Bombonato³

et al. 2008

Quím. Nova

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Recebido em 15/1/08; aceito em 27/2/08; publicado na web em 2/4/09The bioreduction of a series of substituted α-tetralones, carried out using Daucus carota root (carrot), afforded the corresponding homochiral α-tetralols in variable conversions (9 to 90%) and excellent enantiomeric excesses. Two of the assayed α-tetralones were resistant to the bioreduction conditions. The absolute configurations of four α-tetralols were assigned as being (S), by comparison to the (S)-enantiomers obtained by kinetic resolution promoted by CALB-catalysed acetylation. Additionally, the new 5-methoxy-6-methyl-1-tetralone was synthesized in seven steps from 3-methylsalicylic acid.

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“…Reações biocatalisadas podem ser realizadas por enzimas provenientes de microrganismos ou plantas. Grande atenção vem sendo dada às reações químicas usando culturas de células de plantas e partes de plantas como biocatalisadores34,35,36 .Por exemplo, as plantas estão sendo usadas para degradação de poluentes orgânicos (fitorremediação)37 , biorredução de cetonas 38 , lactonização39 , reações de hidrólise40 , hidroxilação e oxidação41 .O uso de extratos brutos e/ou tecidos vegetais pode apresentar em alguns apresentam controle rigoroso na emissão de poluentes. Além disso, gradativamente, a química verde vem sendo incorporada ao meio acadêmico, no ensino e na pesquisa de países em desenvolvimento.…”

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Biorreciclagem de hexano e estudo de reações de óxido-redução usando plantas comestíveis

Utsunomiya¹

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ROBERTO SUSUMU UTSUNOMIYA Biorreciclagem de hexano e estudo de reações de óxido-redução usando plantas comestíveisSão Paulo Data do depósito na SPG: 11/02/2008 2 ROBERTO SUSUMU UTSUNOMIYA Biorreciclagem de hexano e estudo de reações de óxido-redução usando plantas comestíveis DEDICATÓRIA Especialmente à minha família, pelo apoio incondicional e por ter compreendido a minha ausência em muitos momentos especiais. 4 AGRADECIMENTOS Ao professor orientador Dr. Leandro Helgueira de Andrade pela dedicada e primorosa orientação, pelos inestimáveis conselhos e ensinamentos e pela serenidade mantida durante todo o trabalho. Aos professores Dr. João Valdir Comasseto e Dr. André Luis Meleiro Porto pelas preciosas discussões, sugestões e essenciais contribuições. À Dra. Patrícia Busko Di Vitta, que nos auxiliou nas análises cromatográficas; Ao professor Dr. Cassius Vinicius Stevani, que nos possibilitou a quantificação das proteínas e a determinação da atividade enzimática relacionadas ao fungo A. terreus; ao professor Dr. Paulo Roberto Hrihorowitsch Moreno, que nos auxiliou com importantes discussões durante o estudo das reações de óxido-redução mediadas pelas plantas; à professora Dra. Liliana Marzorati pelas ricas discussões e sugestões.

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Enantioselective hydrolysis of 1-aryl ethyl acetates and reduction of aryl methyl ketones using carrot, celeriac and horseradish enzyme systems

Cited by 39 publications

References 7 publications

Plant-Mediated Enantioselective Transformation of Indan-1-One and Indan-1-ol

Plant-Mediated Enantioselective Transformation of Indan-1-One and Indan-1-ol

Bioreduction of substituted a-tetralones promoted by Daucus carota root

Biorreciclagem de hexano e estudo de reações de óxido-redução usando plantas comestíveis

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