Microbial cells as catalysts for stereoselective red–ox reactions

Carballeira, José Daniel; Quezada, Michelle; Hoyos, Pilar; Simeó, Yolanda; Hernáiz, María J.; Alcántara, Andrés R.; Sinisterra, J. V.

doi:10.1016/j.biotechadv.2009.05.001

Cited by 156 publications

(104 citation statements)

References 172 publications

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“…Further improvement of biocatalytic performance of BVMOs may be achieved by several strategies and immobilization of wholecells is among them. The immobilization of cells is mainly considered when there is a need of easy biocatalyst removal from reaction mixture, reuse of biocatalyst, continuous mode of reaction, and increase of biocatalyst concentration (Carballeira et al 2009). Significant progress in biocatalytic performance and characterization of recombinant whole-cell BVMOs has been achieved utilizing encapsulation of cells within polyelectrolyte complex (PEC) capsules and entrapment in polyvinyl alcohol particles.…”

Section: Immobilization Of Whole-cells Expressing Bvmosmentioning

confidence: 99%

Baeyer-Villiger oxidations: biotechnological approach

Bučko

Gemeiner

Schenkmayerová

et al. 2016

Appl Microbiol Biotechnol

100

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Baeyer-Villiger monooxygenases (BVMOs) are a very well-known and intensively studied class of flavin-dependent enzymes. Their substrate promiscuity, high chemo-, regio-, and enantioselectivity are prerequisites for the use in synthetic chemistry and should pave the way for successful industrial processes. Nonetheless, only a very limited number of industrial relevant transformations are known, mainly due to the lack of BVMOs stability and cofactor dependency. In this review, we focus on novel BVMO-mediated transformations, BVMOs in cascade type reactions, potential industrial applications, and how limitations have been tackled by the community. Special attention will be put on whole-cell immobilization strategies. We emphasize to bridge recent developments in fundamental research to industrial applications.

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Section: Immobilization Of Whole-cells Expressing Bvmosmentioning

confidence: 99%

Baeyer-Villiger oxidations: biotechnological approach

Bučko

Gemeiner

Schenkmayerová

et al. 2016

Appl Microbiol Biotechnol

100

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“…Microbial biotransformation by the whole cell microorganisms is often advantageous as compared to isolated enzymes; it is respected economically and ecologically a competitive tool for the biotechnological professionals in search of new techniques to manufacture clean valuable chemicals, pharmaceutical, and agrochemical compounds [8,9]. The enzymes are more stable in the long run as compared to free enzymes as the enzymes in cells are protected from the external environment [10].…”

Section: Introductionmentioning

confidence: 99%

Whole Cell Biocatalyst for Soyasapogenol B Production from Soybean Saponin

Amin¹,

Elsoud²,

Sahab³

2016

Open Conf. Proceed. J.

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Soyasapogenol B (SB), aglycone of soybean saponin, is known to have hepatoprotective, antimutagenic, antivirus, and anti-inflammatory activities. This research examined the use of whole-cell biocatalyst to produce SB from soybean saponin. It was found that Aspergillus flavus, a fungus isolated from peanut pods, was capable of expressing extracellular and intracellular saponin hydrolase enzyme. However, the total enzyme activity produced using fungal whole cells (37U) in the reaction mixture was about 3 times that produced using the extracellular (12.4U) or intracellular (11.5U) enzyme. Cells with maximum hydrolytic activity for production of SB (12.2 U/g) was obtained using production medium supplemented by 2% soybean saponin, as inducer for enzyme production, adjusted at pH 9 and incubated at 30°C for 2 days. The highest yield of SB was achieved when the reaction mixture was incubated at pH 5.5 and 45°C for 48h; using 20% wet cells (corresponding to 4% cell dry weight) and soybean saponin (2%, w/v) as a substrate. Under these optimal conditions, the cells bioconversion efficiency (SB yield) increased from 5.3 to 60%. Whole cell biocatalyst has several advantages with regard to industrial applications: a consistent quality, easy to be prepared and a very low price compared with purified enzyme. Consequently, this study is significant for production of SB from soybean saponin on an industrial scale.

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“…Adicionalmente, a utilização de células íntegras evita os processos de isolamento e purificação da enzima, os quais podem ter um alto custo e como as enzimas dentro das células estão protegidas do ambiente externo, na maioria das vezes, são mais estáveis a longo prazo do que quando isoladas (CARBALLEIRA et al, 2009;HOUNG et al, 2003;ISHIGE;HONDA;SHIMIZU, 2001). A biotransformação, então, pode ser realizada com a adição do substrato ao meio biocatalítico, o qual fornecerá as enzimas, os cofatores e o sistema de regeneração necessários para a formação do produto.…”

Section: Biocatáliseunclassified

“…Podem ser encontradas isoladas (MONTI et al, 2011) ou contidas em células íntegras de micro-organismos (BRENNA et al, 2012;CARBALLEIRA et al, 2009;FABER, 2011;BOMMARIUS, 2011;WINKLER et al, 2012). Entre elas, as desidrogenases destacam-se pelo seu amplo uso em reações de biorredução de substratos pró-quirais para a produção de compostos opticamente ativos (Esquema 1) (CARBALLEIRA et al, 2009;FABER, 2011;BOMMARIUS, 2011).…”

Section: Biorredução Dos Compostos Carbonílicos αβ-Insaturados Mediaunclassified

“…Entre elas, as desidrogenases destacam-se pelo seu amplo uso em reações de biorredução de substratos pró-quirais para a produção de compostos opticamente ativos (Esquema 1) (CARBALLEIRA et al, 2009;FABER, 2011;BOMMARIUS, 2011). A álcool desidrogenase (ADH), também conhecida por carbonila redutase, tem sido comumente utilizada para a preparação de álcoois enriquecidos enantiomericamente por meio da redução de grupos carbonilas (CARBALLEIRA et al, 2009;FABER, 2011;MILAGRE et al, 2009;MONTI et al, 2011;NAKAMURA et al, 2003 Entre os diversos micro-organismos que apresentam a ene redutase e, consequentemente, a capacidade de reduzir assimetricamente a ligação dupla (MULLER; HAUER; ROSCHE, 2006;WINKLER et al, 2012), o Saccharomyces cerevisiae ocupa um lugar especial, pois historicamente, ele foi o primeiro biocatalisador adotado para sínteses assimétricas e gerou compostos quirais com alto ee (BRENNA et al, 2012;SERVI, 1990).…”

Section: Biorredução Dos Compostos Carbonílicos αβ-Insaturados Mediaunclassified

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Biorredução de compostos carbonílicos alfa,beta-insaturados visando à síntese de substâncias opticamente ativas

Silva¹

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Palavras-chave: Biorredução, compostos carbonílicos α,β-insaturados, micro-organismo, Saccharomyces cerevisiae. In recent years, the preparation of enantiomerically pure compounds has become a concern and a challenge to the industry. This fact is a consequence of the tenuous relationship between the spatial structure of substances and the different flavors, odors, pharmacokinetic and pharmacodynamic processes and toxicity that they play in the body. In this context, the asymmetric synthesis of α-alkyl substituted optically active carbonyl compounds has received great attention because they are important building blocks in the synthesis of chiral drugs and natural products. Thus, this study aimed to develop methodologies that allow the preparation of this enantiomerically pure compounds by controlling the formation of stereogenic centers using biocatalysis. To this end, various activated olefins substituted with electron withdrawing groups (carbonyl) were synthesized using two procedures, aldol condensation and esterification reactions. These α,β-unsaturated carbonyl compounds were obtained in good yields (48-94%) and subjected to the biocatalytic reduction mediated by whole cells of microorganisms. Initially, we used the olefin (E)-3-methyl-4-phenyl-3-buten-2-one (51a) as a model substrate for the optimization of the experimental conditions and determine wich one provide the product with better conversion and enantiomeric purity. In these tests, we evaluated various reaction parameters such as the composition of the reaction medium (aqueous, biphasic and buffer), the presence of additives (glucose and phase transfer catalyst), different microorganisms and adsorbing effect of using Amberlite XAD-7. Thus, the biorreduction in aqueous medium, without additives, mediated by LSC-II yeast and with the application of Amberlite XAD-7 was the reaction condition that presented the best enantiomeric excess (81%) and was selected for a methodological study that evaluated the steric and electronic effects of the substituents. It was observed that the substituent in the β-position of the aryl group, the size increase of the α-substituent and the presence of an ester group had an important role in the stereoselectivity of the reaction. Finally, application of the methodology on muguesia enantioselective synthesis, a floral fragrance, was evaluated. The results obtained showed the high potential of the methodology in chemoselective bioreduction of α,β-unsaturated carbonyl compounds and preparation of optically active substances.

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Microbial cells as catalysts for stereoselective red–ox reactions

Cited by 156 publications

References 172 publications

Baeyer-Villiger oxidations: biotechnological approach

Baeyer-Villiger oxidations: biotechnological approach

Whole Cell Biocatalyst for Soyasapogenol B Production from Soybean Saponin

Biorredução de compostos carbonílicos alfa,beta-insaturados visando à síntese de substâncias opticamente ativas

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