Highly enantioselective reduction of the C–C double bond of N-phenyl-2-methyl- and N-phenyl-2,3-dimethyl- maleimides by fungal strains

Sortino, Maximiliano; Filho, Valdir Cechinel; Zacchino, Susana

doi:10.1016/j.tetasy.2009.04.009

Cited by 11 publications

(14 citation statements)

References 15 publications

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“…In this paper we present a biocatalytic route to obtain “natural” 1 and both ( R )- and ( S )- 2 in only one step from 3 through biotransformation with filamentous fungi. The predominant driving forces for selecting this fungal panel were that some of these fungi have previously given rise to bio-reduction products that have the opposite stereochemistry to the predicted by Prelog [ 28 ], or have demonstrated enoate-reductase ability in our previous works [ 29 ].…”

Section: Introductionmentioning

confidence: 99%

Efficient Production of the Flavoring Agent Zingerone and of both (R)- and (S)-Zingerols via Green Fungal Biocatalysis. Comparative Antifungal Activities between Enantiomers

Svetaz

Liberto

Zanardi

et al. 2014

IJMS

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Zingerone (1) and both chiral forms of zingerol (2) were obtained from dehydrozingerone (3) by biotransformation with filamentous fungi. The bioconversion of 3 with A. fumigatus, G. candidum or R. oryzae allowed the production of 1 as the sole product at 8 h and in 81%–90% at 72 h. In turn, A. flavus, A. niger, C. echinulata, M. circinelloides and P. citrinum produced 1 at 8 h, but at 72 h alcohol 2 was obtained as the major product (74%–99%). Among them, A. niger and M. circinelloides led to the anti-Prelog zingerol (R)-2 in only one step with high conversion rates and ee. Instead, C. echinulata and P. citrinum allowed to obtain (S)-2 in only one step, with high conversion rates and ee. Both chiral forms of 2 were tested for antifungal properties against a panel of clinically important fungi, showing that (R)-, but not (S)-2 possessed antifungal activity.

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Section: Introductionmentioning

confidence: 99%

Efficient Production of the Flavoring Agent Zingerone and of both (R)- and (S)-Zingerols via Green Fungal Biocatalysis. Comparative Antifungal Activities between Enantiomers

Svetaz

Liberto

Zanardi

et al. 2014

IJMS

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“…For example, the enantiopure succinimides 4b are building blocks for the synthesis of biologically active natural products, such as, pyrrolizidine and indolizidine alkaloids (Hegazy et al 2006). Although it has been achieved using other enoate reductases (Hegazy et al 2006;Sortino and Alicia Zacchino 2010;Sortino et al 2009), the reported substrate concentration only reached 5 mM (0.94 g/l). On the contrary, the present system can well tolerate a substrate concentration of 54 mM (10 g/l).…”

Section: Discussionmentioning

confidence: 99%

Asymmetric bioreduction of activated alkenes by a novel isolate of Achromobacter species producing enoate reductase

Liu

Pei

Lin

et al. 2012

Appl Microbiol Biotechnol

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The strain Achromobacter sp. JA81, which produced enoate reductase, was applied in the asymmetric reduction of activated alkenes. The strain could catalyze the bioreduction of alkenes to form enantiopure (R)-β-aryl-β-cyano-propanoic acids, a precursor of (R)-γ-amino butyric acids, including the pharmaceutically active enantiomer of the chiral drug (R)-baclofen with excellent enantioselectivity. It could catalyze as well the stereoselective bioreduction of other activated alkenes such as cyclic imides, β-nitro acrylates, and nitro-alkenes with up to >99 % ee and >99 % conversion. The draft genome sequencing of JA81 revealed six putative old yellow enzyme homologies, and the transcription of one of them, Achr-OYE3, was detected using reverse transcription polymerase chain reaction. The recombinant Escherichia coli expressing Achr-OYE3 displayed enoate reductase activity toward (Z)-3-cyano-3-phenyl-propenoic acid (2a).

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“…The results are summarized in Table 2. As a positive control, we performed the bioreduction of 2a and 3a with Aspergillus fumigatus, since OYE ER activity has been reported for this fungal species (Sortino et al, 2009) (experiments are described in the Supplementary Material).…”

Section: Substrate Scope For Selected Biocatalystsmentioning

confidence: 99%

Plant tissue cultures as sources of new ene- and ketoreductase activities

Magallanes-Noguera

Cecati

Mascotti

et al. 2017

Journal of Biotechnology

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While many redox enzymes are nowadays available for synthetic applications, the toolbox of ene-reductases is still limited. Consequently, the screening for these enzymes from diverse sources in the search of new biocatalyst suitable for green chemistry approaches is needed. Among 13 plant tissue cultures, Medicago sativa and Tessaria absinthioides calli, as well as Capsicum annuum hairy roots, were selected due to their ability to hydrogenate the CC double bond of the model substrate 2-cyclohexene-1-one. The three axenic plant cultures showed more preference toward highly activated molecules such as nitrostyrene and maleimide rather than the classical substrates of the well-known Old Yellow Enzymes, resembling the skills of the NAD(P)H-dependent flavin-independent enzymes. When the three biocatalytic systems were applied in the reduction of chalcones, T. absinthioides showed high chemoselectivity toward the CC double bond whereas the other two demonstrated abilities to biohydrogenate the CC double bounds and the carbonyl groups in a sequential fashion.

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Highly enantioselective reduction of the C–C double bond of N-phenyl-2-methyl- and N-phenyl-2,3-dimethyl- maleimides by fungal strains

Cited by 11 publications

References 15 publications

Efficient Production of the Flavoring Agent Zingerone and of both (R)- and (S)-Zingerols via Green Fungal Biocatalysis. Comparative Antifungal Activities between Enantiomers

Efficient Production of the Flavoring Agent Zingerone and of both (R)- and (S)-Zingerols via Green Fungal Biocatalysis. Comparative Antifungal Activities between Enantiomers

Asymmetric bioreduction of activated alkenes by a novel isolate of Achromobacter species producing enoate reductase

Plant tissue cultures as sources of new ene- and ketoreductase activities

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