Semicontinual synthesis of alkyl galactosides using β-galactosidase entrapped in polyvinylalcohol hydrogel

Hronská, Helena; Mastihuba, Vladimı́r; Tokošová, Silvia; Rosenberg, Michal

doi:10.1080/10242422.2016.1247827

Cited by 11 publications

(5 citation statements)

References 14 publications

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“…Acceptor concentration above the optimum value may cause gradual inhibition of the enzyme, as a result, decreasing both hydrolytic and transglycosylation activity of the reaction. 88 Similar observation was reported by Cruz-Guerrero et al, 89 in which the productivity of propyl-βglucoside from o-nitrophenol-β-D-glucopyranoside (oNPG) was reduced as a consequence of lowering the water activity in parallel with the increment of 1-propanol concentration. The increase of acceptor concentration reduced the water activity and also likewise led to full suppression of the hydrolytic reaction.…”

Section: Parameters Affecting the Enzymatic Synthesis Of S-apg 3131 W...supporting

confidence: 78%

“…Acceptor concentration is one of the key determinants of the enzyme reaction which contributes to the water activity of the reaction medium. Acceptor concentration above the optimum value may cause gradual inhibition of the enzyme, as a result, decreasing both hydrolytic and transglycosylation activity of the reaction . Similar observation was reported by Cruz-Guerrero et al, in which the productivity of propyl-β-glucoside from o-nitrophenol-β- d -glucopyranoside (oNPG) was reduced as a consequence of lowering the water activity in parallel with the increment of 1-propanol concentration.…”

Section: Production Of S-apg Through Biological Routesupporting

confidence: 77%

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Toward Sustainable Production of Sugar-Based Alkyl Polyglycoside Surfactant─A Comprehensive Review on Synthesis Route and Downstream Processing

Chin

Shahruddin

Chua

et al. 2023

Ind. Eng. Chem. Res.

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This review aims to identify the challenges and opportunities in sustainable production of sugar-based alkyl polyglycoside, s-APG, by first assessing and subsequently comparing the production route and downstream processing for both the chemically and biologically catalyzed synthesis process, from the perspective of critical operating parameters, type of reactor technologies, and downstream processing strategies. From a sustainability point-view, the acidic homogeneous catalyst in chemically catalyzed s-APG production should be substituted by a practically active, stable, and recyclable heterogeneous catalyst. Alternatively, the green solvent could be used to increase the interaction between sugar and fatty alcohol, resulting in high yield s-APG without using a catalyst. To make the process employing biocatalyst more economically competitive, the free enzyme must be reused through the immobilization method, reactor intensified with membrane or other appropriate downstream processes. A less energy-intensive extraction process to replace the existing evaporative method to separate fatty alcohol from s-APG also deserves an intensive investigation.

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Section: Parameters Affecting the Enzymatic Synthesis Of S-apg 3131 W...supporting

confidence: 78%

Section: Production Of S-apg Through Biological Routesupporting

confidence: 77%

Toward Sustainable Production of Sugar-Based Alkyl Polyglycoside Surfactant─A Comprehensive Review on Synthesis Route and Downstream Processing

Chin

Shahruddin

Chua

et al. 2023

Ind. Eng. Chem. Res.

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show abstract

“…This Y value is remarkably higher than the values reported by Vera et al (2017b) and Ismail et al (1999), where maximum values of 0.58 and 0.79 mol mol −1 were obtained, respectively. Also, it is higher than reported for the closely related synthesis of propyl-β-galactoside (Hronská et al, 2016;Vera et al, 2017c).…”

Section: Synthesis Of Butyl-β-galactoside In a Ternary Systemcontrasting

confidence: 60%

“…The values shown in Table 2 are among the highest reported in the literature for the synthesis of alkyl-glycosides with immobilized enzymes. For instance, Hronská et al (2016) attained Y values around 0.46 and 0.40 mol mol –1 for the synthesis of ethyl- and propyl-β-galactoside with A. oryzae β-galactosidase entrapped in Lentikat ® . Kumar et al (2017) only reported the capability of the β-glucosidase from Streptomyces griseus immobilized onto zinc oxide nanoparticles to synthetize propyl-, butyl-, pentyl-, hexyl- octyl-, benzyl- and 2-phenyl-ethyl glucosides.…”

Section: Resultsmentioning

confidence: 99%

“…However, enzymatic synthesis has some drawbacks, such as a lower yield than obtained in chemical synthesis. Yield typically decreases as molecular weight of the fatty alcohol increases ( Rather and Mishra, 2013 ) so that the enzymatic production of AGs is only efficient for those having a short tail ( Hronská et al, 2016 ; Vera et al, 2017a , b , c ). Since AGs having tails with more than 8 carbon atoms are required for most industrial applications ( Gaudin et al, 2019 ), the synthesis of AG with shorter tails has been relatively less reported.…”

Section: Introductionmentioning

confidence: 99%

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Synthesis of Butyl-β-D-Galactoside in the Ternary System: Acetone/1-Butanol/Aqueous Solution

Ahumada

Arenas

Martínez‐Gómez

et al. 2020

Front. Bioeng. Biotechnol.

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The enzymatic synthesis of short-tailed alkyl glucosides is generally carried out in an aqueous-organic biphasic reaction medium with a rather low fatty alcohol concentration in the aqueous phase (where the synthesis occurs). Thus, hydrolytic reactions have a significant impact on the synthesis performance. Given this background, the use of acetone as cosolvent was studied for the synthesis of butyl-β-galactoside with Aspergillus oryzae β-galactosidase. The liquid-liquid equilibrium of the reaction mixture components (acetone/1-butanol/aqueous solution) was determined and the single-and two-phase regions were defined at 30, 40, and 50 • C. It was observed that the liquidliquid equilibrium of the ternary system acetone/1-butanol/water differs significantly from the one obtained using an aqueous solution (50 mM McIlvaine buffer pH 4.5; 5 g L −1) instead of water. This is mainly because of the salting-out effect of the buffer; nevertheless, the presence of lactose also altered the equilibrium. Having this in mind, the effects of temperature (30 and 50 • C) and reaction mixture composition were assessed. Three general conditions were evaluated: single-phase ternary system (30% acetone), two-phase ternary system (10% acetone) and two-phase binary system (0% acetone). Acetone had a deleterious effect on enzyme stability at 50 • C, leading to low reaction yields. However, no enzyme deactivation was detected at 30 • C. Moreover, a reaction yield of 0.98 mol mol −1 was attained in the 30/50/20% (w/w) mixture of acetone/1-butanol/aqueous solution. This very high yield can be explained by the huge increase in the concentration of 1-butanol and the reduction of water activity. The synthesis was carried out using also the β-galactosidase immobilized in glyoxalagarose and amino-glyoxal-agarose, and by aggregation and crosslinking. In the case of agarose-derived catalysts, two average particle diameters were assessed to evaluate the presence of internal mass transfer limitations. Best yield (0.88 mol mol −1) was obtained with glyoxal-agarose derivatives and the particle size had non-effect on yield. The chemical structure of butyl-β-galactoside was determined by NMR and FT-IR.

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Glycosyl hydrolase catalyzed glycosylation in unconventional media

Chen

Jin

Zhu

et al. 2020

Appl Microbiol Biotechnol

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Semicontinual synthesis of alkyl galactosides using β-galactosidase entrapped in polyvinylalcohol hydrogel

Cited by 11 publications

References 14 publications

Toward Sustainable Production of Sugar-Based Alkyl Polyglycoside Surfactant─A Comprehensive Review on Synthesis Route and Downstream Processing

Toward Sustainable Production of Sugar-Based Alkyl Polyglycoside Surfactant─A Comprehensive Review on Synthesis Route and Downstream Processing

Synthesis of Butyl-β-D-Galactoside in the Ternary System: Acetone/1-Butanol/Aqueous Solution

Glycosyl hydrolase catalyzed glycosylation in unconventional media

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