The isomerization of d-glucose into d-fructose in aqueous alkaline solutions

Kooyman, C.; Vellenga, K.; Wilt, H.G.J. de

doi:10.1016/s0008-6215(77)80003-7

Cited by 78 publications

(76 citation statements)

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“…The Ea of the AlCl3-catalyzed glucose-tofructose isomerization was estimated to be 110 ± 2 kJ·mol -1 (Figure 1e), which was higher than that of CrCl3 catalyst (59~64 kJ·mol -1 ) 17,20 and compatible to that of Sn-Beta (85~108 kJ·mol -1 ) 7,9,10 or some typical base catalysts such as NaOH and hydrotalcite (121~129 kJ·mol -1 ). [41][42][43] 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 37 38 39 40 41 42 43 44 45 46 47 48 49 50 51 52 53 54 55 56 57 58 59 60 The activity of AlCl3 was also compared with that of CrCl3, SnCl4, and Sn-Beta under the same reaction conditions. The results are shown in Table 1 and Figure S1.…”

Section: Methodsmentioning

confidence: 99%

Mechanistic Study of Glucose-to-Fructose Isomerization in Water Catalyzed by [Al(OH)₂(aq)]⁺

et al. 2015

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The nature of the active aluminum species and their interaction with glucose in water are studied to establish a detailed mechanism for understanding the AlCl3-catalyzed glucose-tofructose isomerization. The combination of activity results with electrospray ionization tandem mass spectrometry (ESI-MS/MS) reveal that [Al(OH)2(aq)] + species contributes a lot to the isomerization. Attenuated total reflection infrared spectroscopy (ATR-IR) results show that glucose undergoes a ring-opening process which is accelerated by the [Al(OH)2(aq)] + species. The binding of acyclic glucose with [Al(OH)2(aq)] + species occurs at the C1-O and C2-O positions of glucose, which initiates the hydride shift of the aldose-to-ketose isomerization. The in-situ 27 Al NMR data elucidate the maintenance of the hexa-coordinated form of Al species throughout the reaction. An obvious kinetic isotope effect (KIE) occurs with the C2 deuterium-labeled glucose, confirming that the intramolecular hydride shift from the C2 to C1 positions of glucose is the ratelimiting step for the isomerization. The apparent activation energy (Ea) of the AlCl3-catalyzed glucose-to-fructose isomerization reaction is estimated to be 110 ± 2 kJ·mol -1 .

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Section: Methodsmentioning

confidence: 99%

Mechanistic Study of Glucose-to-Fructose Isomerization in Water Catalyzed by [Al(OH)₂(aq)]⁺

et al. 2015

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“…Other reactions, such as aldolization/retro-aldolization, β-elimination and benzylic rearrangement [8][9][10][11] also contribute to formation of side products. The mechanism of isomerization reaction ( Fig.…”

Section: Introductionmentioning

confidence: 99%

Aldose to ketose interconversion: galactose and arabinose isomerization over heterogeneous catalysts

Murzin

Murzina

Aho

et al. 2017

Catal. Sci. Technol.

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Isomerization of glucose, galactose and arabinose to corresponding keto-sugars was studied in the present work over a range of heterogeneous catalysts. Magnesium aluminates with different ratios between oxides resulting in materials with a Mg/Al ratio from 0.2 to 0.9 were prepared, characterized and evaluated in terms of their catalytic behavior. The catalyst with a Mg/Al ratio close to hydrotalcites was the most efficient considering activity, selectivity and stability. The sugar structure was shown to have a minor influence on catalytic activity and selectivity.

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“…3. Parallel to the heterogeneous enzymatically catalyzed reaction the homogeneous alkaline isomerization takes place. 4 The rate of this reaction has been determined experimentally. Hence, the rate of the enzymatically catalyzed reaction can be calculated from the experimentally determined overall reaction rate minus the rate of the homogeneous alkaline isomerization.…”

Section: Methodsmentioning

confidence: 99%

The isomerization ofD-glucose intoD-fructose catalyzed by whole-cell immobilized glucose isomerase. The dependence of the intrinsic rate of reaction on substrate concentration, pH, and temperature

Kikkert

Vellenga

Wilt

et al. 1981

Biotechnol. Bioeng.

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SummaryThe relation between the intrinsic rate of the glucose-fructose isomerization catalyzed by whole-cell immobilized glucose isomerase and the substrate concentration can be described with the kinetic model ki kz G + E C X E C j ; l _ i L F + EThe numerical values of kl , k -k2. and k 2 have been determined from low-conversion experiments starting from pure glucose or fructose solutions, and are presented as a function of pH and temperature. The difference between the overall chemical reaction rate determined in high-conversion experiments and that calculated from the individual k , , k -,, k2, and k-2 values is less than 10%.

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The isomerization of d-glucose into d-fructose in aqueous alkaline solutions

Cited by 78 publications

References 13 publications

Mechanistic Study of Glucose-to-Fructose Isomerization in Water Catalyzed by [Al(OH)₂(aq)]⁺

Mechanistic Study of Glucose-to-Fructose Isomerization in Water Catalyzed by [Al(OH)₂(aq)]⁺

Aldose to ketose interconversion: galactose and arabinose isomerization over heterogeneous catalysts

The isomerization ofD-glucose intoD-fructose catalyzed by whole-cell immobilized glucose isomerase. The dependence of the intrinsic rate of reaction on substrate concentration, pH, and temperature

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The isomerization of d-glucose into d-fructose in aqueous alkaline solutions

Cited by 78 publications

References 13 publications

Mechanistic Study of Glucose-to-Fructose Isomerization in Water Catalyzed by [Al(OH)2(aq)]+

Mechanistic Study of Glucose-to-Fructose Isomerization in Water Catalyzed by [Al(OH)2(aq)]+

Aldose to ketose interconversion: galactose and arabinose isomerization over heterogeneous catalysts

The isomerization ofD-glucose intoD-fructose catalyzed by whole-cell immobilized glucose isomerase. The dependence of the intrinsic rate of reaction on substrate concentration, pH, and temperature

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Mechanistic Study of Glucose-to-Fructose Isomerization in Water Catalyzed by [Al(OH)₂(aq)]⁺

Mechanistic Study of Glucose-to-Fructose Isomerization in Water Catalyzed by [Al(OH)₂(aq)]⁺