Enolisation and isomerisation of monosaccharides in aqueous, alkaline solution

Wit, G. de; Kieboom, A. P. G.; Bekkum, H. van

doi:10.1016/s0008-6215(00)84773-4

Cited by 124 publications

(112 citation statements)

References 26 publications

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“…When in contact with the catalyst surface, the glucose C‐2 is deprotonated, resulting in the formation of the 1,2‐enediol intermediate followed by electron pair movement through the carbon skeleton towards the formation of fructose. In contrast, the respective electron transfer for mannose formation is considerably slower . The postulated reaction mechanism is depicted schematically in Scheme .…”

Section: Resultsmentioning

confidence: 99%

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Glucose to Fructose Isomerization in Aqueous Media over Homogeneous and Heterogeneous Catalysts

et al. 2016

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Isomerization of glucose to fructose is an important reaction with numerous applications in terms of biomass valorization. The reaction is catalyzed enzymatically but may also proceed under alkaline conditions, in which case it is accompanied by low selectivity and formation of byproducts. Solid Lewis acid and basic catalytic materials are being studied as alternative catalysts. In this work, the isomerization of glucose to fructose in aqueous media over homogeneous and heterogeneous catalysts has been investigated. The effect of polar aprotic solvents and their mixtures with water on glucose conversion and fructose selectivity was also studied. Sodium aluminate (NaAlO2) has been proven to be very effective, resulting in high fructose yield (52.1 %) and high selectivity (84.8 %). Among the various solid catalysts tested, MgO afforded glucose conversion of 44 %, with 75.8 % and 33.4 % fructose selectivity and yield, respectively, when the isomerization reaction was conducted in neat H2O.

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Section: Resultsmentioning

confidence: 99%

“…In contrast, the respective electront ransfer for mannosef ormation is considerably slower. [14,60] The postulated reactionm echanism is depicted schematically in Scheme 2.…”

Section: B( In the Supportingi Nformation)mentioning

confidence: 99%

Glucose to Fructose Isomerization in Aqueous Media over Homogeneous and Heterogeneous Catalysts

et al. 2016

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“…Enediolization of monosaccharides in the alkaline medium is readily detected by UV/vis spectroscopy as a characteristic absorption band with the maximum at 290-310 nm, which undergoes blue-shift with a decrease in pH. [18,49] The introduction of Ca 2 + into alkaline solutions of monosaccharides produces a red-shift of the maxima up to 325-342 nm, thus indicating the complexation of enediols with calcium cations (Figure 3). [50] It is remarkable that other alkaline-earth metal cations (Sr 2 + , Ba 2 + , and Mg 2 + ) cause indiscernible changes in the UV/vis spectra of enediols of monosaccharides.…”

Section: Initiation Of the Formose Reaction And The Formation Of Monomentioning

confidence: 99%

Catalytic Formation of Monosaccharides: From the Formose Reaction towards Selective Synthesis

et al. 2014

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The formose reaction (FR) has been long the focus of intensive investigations as a simple method for synthesis of complex biologically important monosaccharides and other sugar-like molecules from the simplest organic substrate-formaldehyde. The fundamental importance of the FR is predominantly connected with the ascertainment of plausible scenarios of chemical evolution which could have occurred on the prebiotic Earth to produce the very first molecules of carbohydrates, amino- and nucleic acids, as well as other vitally important substances. The practical importance of studies on the FR is the elaboration of catalytic methods for the synthesis of rare and non-natural monosaccharides and polyols. This Minireview considers the FR from the point of view of chemists working in the field of catalysis with emphasis on the mechanisms of numerous parallel and consequent catalytic transformations that take place during the FR. Based on its kinetics, the FR may be considered as a non-radical chain process with degenerate branching. The Minireview also considers different approaches to the control of selectivity of carbohydrate synthesis from formaldehyde and lower monosaccharides.

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“…Most studies of homogeneous catalysts have focused on soluble inorganic bases, such as sodium or potassium hydroxide, and organic bases, for example triethylamine [17,[23][24][25][26]. Basic homogeneous catalysts, however, tend to form higher amounts of by-products [17,25].…”

Section: Introductionmentioning

confidence: 99%

Glucose isomerisation into fructose over magnesium-impregnated NaY zeolite catalysts

Graça

Iruretagoyena

Chadwick

2017

Applied Catalysis B: Environmental

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Enolisation and isomerisation of monosaccharides in aqueous, alkaline solution

Cited by 124 publications

References 26 publications

Glucose to Fructose Isomerization in Aqueous Media over Homogeneous and Heterogeneous Catalysts

Glucose to Fructose Isomerization in Aqueous Media over Homogeneous and Heterogeneous Catalysts

Catalytic Formation of Monosaccharides: From the Formose Reaction towards Selective Synthesis

Glucose isomerisation into fructose over magnesium-impregnated NaY zeolite catalysts

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