NMR studies on mechanism of isomerisation of fructose 6-phosphate to glucose 6-phosphate catalysed by phosphoglucose isomerase from Thermococcus kodakarensis

Abbas, Shahzada Nadeem; Mok, K. Hun; Rashid, Naeem; Xie, Yongjing; Ruether, Manuel; O’Brien, John D.; Akhtar, Muhammad

doi:10.1016/j.bioorg.2016.03.004

Cited by 6 publications

(3 citation statements)

References 13 publications

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“…On the basis of calculations and simulations, a zwitterion intermediate-based mechanism consisting both proton and hydride transfers was put forward (Scheme ), which reconciled the controversial mechanisms and rationalized the enzymatic reaction. By using 1 D and 2 D NMR methods, Abbas et al further disclosed that the presence of metal electrophile to activate the carbonyl group of sugars was necessary for both the enediol and hydride shift processes …”

Section: Biocatalytic Processesmentioning

confidence: 99%

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Glucose Isomerization by Enzymes and Chemo-catalysts: Status and Current Advances

et al. 2017

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The well-known interconversion of aldoses to their corresponding ketoses was discovered more than a century ago, but has recently attracted renewed attention due to alternative application areas. Since the pioneering discovery, much work has been directed toward improving the process of isomerization of aldoses in terms of yields, catalysts, solvents, catalytic systems, etc., by both enzymatic and chemo-catalytic approaches. Among aldose–ketose interconversion reactions, fructose production by glucose isomerization to make high-fructose corn syrup (HFCS) is an industrially important and large biocatalytic process today, and a large number of studies have been reported on the process development. In parallel, also alternative chemo-catalytic systems have emerged, as enzymatic conversion has drawbacks, though they are typically more selective and produce fructose under mild reaction conditions. Isomerization of glucose is also a central reaction for making renewable platform chemicals, such as lactic acid, 5-hydroxymethylfurfural (HMF), and levulinic acid. In these other applications, thermally stable catalysts are required, thus making use of enzymatic catalysis inadequate, since enzymes generally possess a limited temperature operating window, typically less than 80 °C. From this viewpoint, the chemo-catalystsespecially solid heterogeneous catalystsare playing a key role for the development of not only making HFCS, but also making chemicals and fuels from glucose via the isomerized product/intermediate fructose. This review focuses on how both enzyme- and chemo-catalysts are being useful for the isomerization of glucose to fructose. Specifically, development of Lewis acid-containing zeolites for glucose isomerization is reviewed in detail, including mechanism, isotopic labeling, and computational studies.

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Section: Biocatalytic Processesmentioning

confidence: 99%

“…By using 1 D and 2 D NMR methods, Abbas et al further disclosed that the presence of metal electrophile to activate the carbonyl group of sugars was necessary for both the enediol and hydride shift processes. 114 3. HOMOGENEOUS CHEMO-CATALYSIS 3.1.…”

Section: Theoretical Studies On Enzymatic Isomerization and Other Asp...mentioning

confidence: 99%

Glucose Isomerization by Enzymes and Chemo-catalysts: Status and Current Advances

et al. 2017

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“…[1][2][3][4][5] In contrast to other renewable energies such as solar, wind and hydro power, biomass is the only feedstock that provides sustainable organic carbon resources for both biofuels and chemicals. [6][7][8][9][10] In this respect, fructose, as an ample and inexpensive six-carbon sugar molecule, has been employed widely for the synthesis of biobased products. For example, the loss of three water molecules from fructose catalyzed by an acid can yield 5-hydroxymethylfurfural, followed by alcoholysis to give alkyl levulinates.…”

Section: Introductionmentioning

confidence: 99%

Phosphotungstic acid heterogenized by assembly with pyridines for efficient catalytic conversion of fructose to methyl levulinate

Fang

Zhao

et al. 2018

RSC Adv.

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TM1385 from Thermotoga maritima functions as a phosphoglucose isomerase via cis-enediol-based mechanism with active site redundancy

Swope

Lake

Barrow

et al. 2021

Biochimica et Biophysica Acta (BBA) - Proteins and Proteomics

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NMR studies on mechanism of isomerisation of fructose 6-phosphate to glucose 6-phosphate catalysed by phosphoglucose isomerase from Thermococcus kodakarensis

Cited by 6 publications

References 13 publications

Glucose Isomerization by Enzymes and Chemo-catalysts: Status and Current Advances

Glucose Isomerization by Enzymes and Chemo-catalysts: Status and Current Advances

Phosphotungstic acid heterogenized by assembly with pyridines for efficient catalytic conversion of fructose to methyl levulinate

TM1385 from Thermotoga maritima functions as a phosphoglucose isomerase via cis-enediol-based mechanism with active site redundancy

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