Immobilisation and flow chemistry: tools for implementing biocatalysis

Coloma, José; Guiavarc’h, Yann; Hagedoorn, Peter‐Leon; Hanefeld, Ulf

doi:10.1039/d1cc04315c

Cited by 29 publications

(26 citation statements)

References 79 publications

(108 reference statements)

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“…This explains its higher productivity. This result is unexpected since flow systems commonly allowed process intensification [25,26,37,45,46]. However, the high concentration (1 M) and low polarity (log P = −0.27) of nitromethane might not maintain a constant a w on Celite-GtHNL-3V.…”

Section: Comparison Between Batch and Continuous Flow Systemsmentioning

confidence: 97%

“…A fair comparison between batch and continuous flow systems can be made based on their space-time-yields (STYs). The product formation over time is not a linear function in batch and flow systems; thus, the comparison must be made at the same level of conversion [25]. Table 2 shows the STYs of the batch and continuous flow systems using MTBE saturated with 100 mM KPi buffer pH 7 as reaction medium.…”

Section: Comparison Between Batch and Continuous Flow Systemsmentioning

confidence: 99%

“…Flow chemistry is an important tool for process intensification and has been reported to reduce reaction times concomitantly improving enantioselectivities by suppressing undesired side reactions. Additionally, it enhances safety and among others reduces reaction volumes [25][26][27][28][29][30][31][32]. At the same time, it requires the enzymes to be immobilised, which often improves enzyme stability.…”

Section: Introductionmentioning

confidence: 99%

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Batch and Flow Nitroaldol Synthesis Catalysed by Granulicella tundricola Hydroxynitrile Lyase Immobilised on Celite R-633

et al. 2022

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Granulicella tundricola hydroxynitrile lyase (GtHNL) catalyses the synthesis of chiral (R)-cyanohydrins and (R)-β-nitro alcohols. The triple variant GtHNL-A40H/V42T/Q110H (GtHNL-3V) was immobilised on Celite R-633 and used in monophasic MTBE saturated with 100 mM KPi buffer pH 7 for the synthesis of (R)-2-nitro-1-phenylethanol (NPE) in batch and continuous flow systems. Nitromethane was used as a nucleophile. A total of 82% of (R)-NPE and excellent enantioselectivity (>99%) were achieved in the batch system after 24 hours of reaction time. GtHNL-3V on Celite R-633 was successfully recycled five times. During more recycling steps a significant decrease in yield was observed while the enantioselectivity remained excellent over eight cycles. The use of a flow system enabled the continuous synthesis of (R)-NPE. A total of 15% formation of (R)-NPE was reached using a flow rate of 0.1 mL min−1; unfortunately, the enzyme was not stable, and the yield decreased to 4% after 4 hours on stream. A similar yield was observed during 15 hours at a rate of 0.01 mL min−1. Surprisingly the use of a continuous flow system did not facilitate the process intensification. In fact, the batch system displayed a space-time-yield (STY/mgenzyme) of 0.10 g L−1 h−1 mgenzyme−1 whereas the flow system displayed 0.02 and 0.003 g L−1 h−1 mgenzyme−1 at 0.1 and 0.01 mL min−1, respectively. In general, the addition of 1 M nitromethane potentially changed the polarity of the reaction mixture affecting the stability of Celite-GtHNL-3V. The nature of the batch system maintained the reaction conditions better than the flow system. The higher yield and productivity observed for the batch system show that it is a superior system for the synthesis of (R)-NPE compared with the flow approach.

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Section: Comparison Between Batch and Continuous Flow Systemsmentioning

confidence: 97%

Section: Comparison Between Batch and Continuous Flow Systemsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Batch and Flow Nitroaldol Synthesis Catalysed by Granulicella tundricola Hydroxynitrile Lyase Immobilised on Celite R-633

et al. 2022

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“…The use of continuous‐flow PBRs based on immobilized biocatalysts not only minimizes biocatalysts exposure to shear forces, but also it overcomes the limited particle loading in stirred tank reactors. The synergy of an efficient immobilization strategy of (multi)enzymatic systems, reactor engineering and control, and process integration for in situ product removal and cofactor recycling can contribute to biocatalytic processes intensification [14,15] …”

Section: Introductionmentioning

confidence: 99%

Biocatalytic Production of a Nylon 6 Precursor from Caprolactone in Continuous Flow

2022

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6-Aminocaproic acid (6ACA) is a key building block and an attractive precursor of caprolactam, which is used to synthesize nylon 6, one of the most common polymers manufactured nowadays. (Bio)-production of platform chemicals from renewable feedstocks is instrumental to tackle climate change and decrease fossil fuel dependence. Here, the cell-free biosynthesis of 6ACA from 6-hydroxycaproic acid was achieved using a coimmobilized multienzyme system based on horse liver alcohol dehydrogenase, Halomonas elongata transaminase, and Lactobacillus pentosus NADH oxidase for in-situ cofactor recycling, with > 90 % molar conversion (m.c.) The integration of a step to synthesize hydroxy-acid from lactone by immobilized Candida antarctica lipase B resulted in > 80 % m.c. of ɛ-caprolactone to 6ACA, > 20 % of δ-valerolactone to 5-aminovaleric acid, and 30 % of γ-butyrolactone to γ-aminobutyric acid in one-pot batch reactions. Two serial packed-bed reactors were set up using these biocatalysts and applied to the continuous-flow synthesis of 6ACA from ɛ-caprolactone, achieving a space-time yield of up to 3.31 g 6ACA h À 1 L À 1 with a segmented liquid/air flow for constant oxygen supply.

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“…28,29 Performance of light-dependent reactions in continuous flow, in particular in microchannels (ID < 1 mm), represents a convenient way of circumventing this issue. 28,29 Although the performance of biocatalytic transformations in continuous flow has been established, [30][31][32][33][34][35][36] examples of flow photobiocatalysis remain scarce and are not of synthetic applicability. 37 Examples include the generation of oxygen by a cyanobacterium for the oxidation of cyclohexene to cyclohexanol, 38 and the photochemical cofactor regeneration for the enzymatic reduction of CO2 to formate.…”

Section: Introductionmentioning

confidence: 99%

Strategies for Transferring Photobiocatalysis to Continuous Flow Exemplified by the Photodecarboxylation of Fatty Acids

Simić

Jakštaitė

Huck

et al. 2022

Preprint

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The challenges of light-dependent biocatalytic transformations of lipophilic substrates in aqueous media are manifold. For instance, photolability of the catalyst as well as insufficient light penetration into the reaction vessel may be further exacerbated by a heterogeneously dispersed substrate. Light penetration may be addressed by performing the reaction in continuous flow, which allows two modes of applying the catalyst: (i) heterogenously, immobilized on a carrier, which requires light-permeable supports, or (ii) homogenously, dissolved in the reaction mixture. Taking the light-dependent photodecarboxylation of palmitic acid catalyzed by the fatty-acid photodecarboxylase from Chlorella variabilis (CvFAP) as a showcase, strategies for the transfer of a photoenzyme-catalyzed reaction into continuous flow were identified. A range of different supports was evaluated for the immobilization of CvFAP, whereby Eupergit C250 L was the carrier of choice. As the photostability of the catalyst was a limiting factor, a homogeneous system was preferred instead of employing the heterogenized enzyme. This implied that photolabile enzymes may preferably be applied in solution if repair mechanisms cannot be provided. Furthermore, when comparing different wavelengths and light intensities, extinction coefficients may be considered to ensure comparable absorption at each wavelength. Employing homogenous conditions in the CvFAP-catalyzed photodecarboxylation of palmitic acid afforded a space-time yield unsurpassed by any reported batch process (5.7 g/L·h, 26.9 mmol/L·h) for this reaction, demonstrating the advantage of continuous flow in attaining higher productivity of photobiocatalytic processes.

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Immobilisation and flow chemistry: tools for implementing biocatalysis

Abstract: The merger of enzyme immobilisation and flow chemistry has attracted the attention of the scientific community during the last years. Immobilisation enhances enzyme stability and enables recycling, flow chemistry allows...

Cited by 29 publications

References 79 publications

Batch and Flow Nitroaldol Synthesis Catalysed by Granulicella tundricola Hydroxynitrile Lyase Immobilised on Celite R-633

Batch and Flow Nitroaldol Synthesis Catalysed by Granulicella tundricola Hydroxynitrile Lyase Immobilised on Celite R-633

Biocatalytic Production of a Nylon 6 Precursor from Caprolactone in Continuous Flow

Strategies for Transferring Photobiocatalysis to Continuous Flow Exemplified by the Photodecarboxylation of Fatty Acids

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