Asymmetric bioreduction of natural xenobiotic diketones by Brassica napus hairy roots

Orden, Alejandro A.; Bisogno, Fabricio R.; Cifuente, Diego Alberto; Giordano, Óscar S.; Kurina-Sanz, Marcela

doi:10.1016/j.molcatb.2006.06.010

Cited by 25 publications

(14 citation statements)

References 25 publications

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“…Figure 27 shows the reduction of a natural bioactive diketone 1-(5-acetyl-2-hydroxyphenyl)-3-methylbut-2-en-1-one to 6-(1(S)-hydroxyethyl)-2,2-dimethyl-2,3-dihydro-4H-chromen-4-one in >97% ee with >78% yield by Brassica napus hairy roots. 41 The diketone was firstly changed to the corresponding chromanone derivative and then reduced to the product.…”

Section: Plant Cell Culture As a Biocatalystmentioning

confidence: 99%

Recent progress in biocatalysis for asymmetric oxidation and reduction

Matsuda

Yamanaka

Nakamura

2009

Tetrahedron: Asymmetry

364

163

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Section: Plant Cell Culture As a Biocatalystmentioning

confidence: 99%

Recent progress in biocatalysis for asymmetric oxidation and reduction

Matsuda

Yamanaka

Nakamura

2009

Tetrahedron: Asymmetry

364

163

View full text Add to dashboard Cite

“…Unfortunately, there are few reports about the biotransformation catalyzed by plant cell [17][18][19][20][21][22]. But the previous reported works is mainly concentrated on natural substrates.…”

Section: Introductionmentioning

confidence: 99%

“…But the previous reported works is mainly concentrated on natural substrates. Excellent results are obtained in natural ketones reduction, since they are easily accepted by plant cell [18][19][20][21][22]. However the asymmetric reduction reaction of non-natural prochiral ketone catalyzed by plant tissue or cell was rarely reported, which is very valuable to both theoretical research and practical application.…”

Section: Introductionmentioning

confidence: 99%

Asymmetric reduction of prochiral ketones to chiral alcohols catalyzed by plants tissue

Yang

Zeng

Yang

et al. 2008

J Ind Microbiol Biotechnol

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As an important organic compound, chiral alcohols are the key chiral building blocks to many single enantiomer pharmaceuticals. Asymmetric reduction of the corresponding prochiral ketones to produce the chiral alcohols by biocatalysis is one of the most promising routes. Asymmetric reduction of different kinds of non-natural prochiral ketones catalyzed by various plants tissue was studied in this work. Acetophenone, 4'-chloroacetophenone and ethyl 4-chloroacetoacetate were chosen as the model substrates for simple ketone, halogen-containing aromatic ketone and beta-ketoesters, respectively. Apple (Malus pumila), carrot (Daucus carota), cucumber (Cucumis sativus), onion (Allium cepa), potato (Soanum tuberosum), radish (Raphanus sativus) and sweet potato (Ipomoea batatas) were chosen as the biocatalysts. It was found that these kinds of prochiral ketoness could be reduced by these plants tissue with high enantioselectivity. Both R- and S-form configuration chiral alcohols could be obtained. The e.e. and chemical yield could reach about 98 and 80% respectively for acetophenone and 4'-chloroacetophenone reduction reaction with favorable plant tissue. And the e.e. and yield for ethyl 4-chloroacetoacetate reduction reaction was about 91 and 45% respectively.

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“…[50] Previous reductions of diketone 1g using plants were reported. [27,51] It remained clear that LBADH was not a suitable enzyme to perform these bioreductions due to low conversions (entries 1 and 4). This is in concordance with the small active site of this biocatalyst.…”

Section: Scheme 2 Promiscuous Binding-modes Of Diketones 1a-c and Hymentioning

confidence: 99%

Promiscuous Substrate Binding Explains the Enzymatic Stereo‐ and Regiocontrolled Synthesis of Enantiopure Hydroxy Ketones and Diols

Kurina-Sanz¹,

Bisogno²,

Lavandera³

et al. 2009

Adv Synth Catal

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Abstract. Regio-and stereoselective reductions of several diketones to afford enantiopure hydroxy ketones or diols were accomplished using isolated alcohol dehydrogenases (ADHs). Results could be rationalised taking into account different (promiscuous) substrate-binding modes in the active site of the enzyme. Furthermore, interesting natural cyclic diketones were also reduced with high regio-and stereoselectivity.Some of the 1,2-and 1,3-diketones used in this study were reduced employing a low excess of the hydrogen donor (2-propanol) due to the quasi-irreversibility of these ADHcatalysed processes. Thus, using less quantity of cosubstrate, scale-up could be easily achieved.

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Asymmetric bioreduction of natural xenobiotic diketones by Brassica napus hairy roots

Cited by 25 publications

References 25 publications

Recent progress in biocatalysis for asymmetric oxidation and reduction

Recent progress in biocatalysis for asymmetric oxidation and reduction

Asymmetric reduction of prochiral ketones to chiral alcohols catalyzed by plants tissue

Promiscuous Substrate Binding Explains the Enzymatic Stereo‐ and Regiocontrolled Synthesis of Enantiopure Hydroxy Ketones and Diols

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