Effective Cleavage of β-1,4-Glycosidic Bond by Functional Micelle with l-Histidine Residue

Liao, Xia; Liu, Ying; Xiao, Pei; Chun, Myung‐Suk; Meng, Xiang‐Gao

doi:10.1007/s10562-016-1745-2

Cited by 5 publications

(3 citation statements)

References 53 publications

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“…To avoid this interference, we used the data of initial reaction time of 3 h to evaluate the values of k cat , K mG and K mF in this work. K mG , K mF and k cat were obtained by nonlinear fitting according to kinetic equations (1) and (2). The calculated results are listed in Table 4.…”

Section: Products Analysis and Reaction Kineticsmentioning

confidence: 99%

“…The utilization of renewable lignocellulosic biomass in the world is extremely important to solve the problems of resource shortage, for example fossil fuels depletion and the pollution of environment, [1][2][3] and glucose is the main product of degradation of biomass. Compared with glucose, fructose is easier to convert into important platform compounds such as hydroxymethylfurfural (HMF), levulinic acid, and other versatile platform chemicals and liquid fuels.…”

Section: Introductionmentioning

confidence: 99%

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Highly Selective Isomerization of Glucose into Fructose Catalyzed by a Mimic Glucose Isomerase

Zhang

Meng

et al. 2019

ChemCatChem

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An amphoteric phenolic compound with carboxyl and amino functional groups was synthesized and used as mimic glucose isomerase to catalyze the isomerization of glucose into fructose. The mimic enzyme displayed excellent catalytic activity for isomerization of glucose to fructose under mild conditions. The yield of fructose and selectivity of fructose could reach 33.0 % and 93.5 % after reacting 4 h, respectively, at pH 8.5 and 80°C. The catalysis reaction rate constant k cat and Michaelis constants K mG , K mF were calculated. The activation energy of glucose to fructose was evaluated as 65.9 kJ mol À 1 . The possible catalysis reaction mechanism was proposed. The acid-base groups on the catalyst play an important role in proton extraction and transfer, as well as in the rotation of local carbon chain, which leads to the highly selective isomerization of glucose into fructose under mild conditions.

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Section: Products Analysis and Reaction Kineticsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Highly Selective Isomerization of Glucose into Fructose Catalyzed by a Mimic Glucose Isomerase

Zhang

Meng

et al. 2019

ChemCatChem

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“…14 The development of enzyme mimics is another attractive nonenzymatic way to hydrolyze glycosidic bonds of nonactivated saccharide. Very recently, functional La(III) metallomicelles 13 and histidine-derivatized 15 micelles have been reported to hydrolyze β-glycosidic bonds in alkaline aqueous solution between 80 and 100 °C. Both studies focus on the hydrolysis of cellobiose as the basic structural unit of cellulose.…”

Section: Introductionmentioning

confidence: 99%

Microgel-Catalyzed Hydrolysis of Nonactivated Disaccharides

2020

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The controlled and selective hydrolysis of underivatized disaccharides and oligosaccharides remains a challenge that is met by enzymatic and nonenzymatic approaches. In an effort to capitalize on recent progress in the development of functional enzyme mimics for the hydrolysis of glycosidic bonds, we developed cross-linked microgels with embedded binuclear copper(II) complexes that are shown here to hydrolyze 1→4 over 1→6 glycosidic bonds under mildly alkaline conditions at elevated temperatures. The microgel catalysts show an unusual preference for the hydrolysis of 1→4β- over 1→4α-glycosidic bonds yielding up to 25 μg L–1 of glucose from cellobiose over 72 h and about half of that during the hydrolysis of maltose after correction for background effects. The experimental results are supported by computational analyses of the interactions between the embedded catalyst and the nonactivated disaccharide in putative transition state structures of the assembly during hydrolysis of the nonactivated glycosidic bond to rationalize this observation.

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Roles of Brønsted-Base and Brønsted-Acid Catalysts for Glucose Isomerization into Fructose and Fructose Dehydration into 5-Hydroxymethylfurfural

Dharmapriya,

Lin,

Huang

2024

Energy Fuels

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5-Hydroxymethylfurfural (5-HMF) holds substantial importance as a foundational chemical that can be potentially transformed into biofuels and various additional high-value products. Fructose is gaining popularity as one of the raw materials for the facile formation of 5-HMF. However, it is not as abundant in nature as glucose, the primary product derived from biomass breakdown and the most abundant monosaccharide globally. Producing fructose through glucose isomerization is an economical approach in this context. This study investigates several types of novel, facile, and reusable hydrogel catalysts for the isomerization of glucose into fructose and dehydration of fructose into 5-HMF in green solvent media. This study marks the first application of both amine and amide functional groups within a single catalyst (PEGDA-DMAPMA) for glucose isomerization. The results of glucose isomerization using Brønsted-base PEGDA-DMAPMA hydrogel catalysts reveal a 45% glucose conversion rate and a 27% fructose yield, with a 61% selectivity at 110 °C, within a 2 h reaction time. Brønsted-acid PEGDA-3SMP-H gave a fructose conversion rate of 93%, yielding 65% 5-HMF at 120 °C after 6 h. A significant observation was made for PEGDA-3SMP-H, indicating an increase in the catalytic ability with regeneration cycles. The synthesized catalysts PEGDA-DMAPMA and PEGDA-3SMP-H exhibited stability up to 120 °C despite an increase in swelling ratio at higher temperatures and times. Furthermore, PEGDA-3SMP-Cu2+ demonstrated a considerable yield of fructose compared to other metal ion-modified Brønsted-acid catalysts. Additionally, an efficient heating method for this process was identified. In conclusion, the prepared hydrogel catalysts are preferred for industrial applications in carbohydrate conversion.

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Effective Cleavage of β-1,4-Glycosidic Bond by Functional Micelle with l-Histidine Residue

Cited by 5 publications

References 53 publications

Highly Selective Isomerization of Glucose into Fructose Catalyzed by a Mimic Glucose Isomerase

Highly Selective Isomerization of Glucose into Fructose Catalyzed by a Mimic Glucose Isomerase

Microgel-Catalyzed Hydrolysis of Nonactivated Disaccharides

Roles of Brønsted-Base and Brønsted-Acid Catalysts for Glucose Isomerization into Fructose and Fructose Dehydration into 5-Hydroxymethylfurfural

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