Syntheses of cellotriose and cellotetraose analogues as transition state mimics for mechanistic studies of cellulases

Noguchi, Shogo; Takemoto, Shintaro; Kidokoro, Shun‐ichi; Yamamoto, Kazunori; Hashimoto, Minoru

doi:10.1016/j.bmc.2011.04.048

Cited by 4 publications

(2 citation statements)

References 31 publications

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“…The anomeric region in the HSQC spectrum of Miscanthus showed the same pattern. Although the anomeric protons on glucopyranosyl residues, adjacent to the reducing end, normally show a distinct chemical shift, compared to the other anomeric protons, our assumption is that this shoulder peak at 103.2/4.27 ppm corresponds to the anomeric linkages adjacent to the reducing ends of the glucan chain. Further support is that the signal intensity roughly equals the sum of the intensities from both α and β reducing ends.…”

Section: Resultsmentioning

confidence: 92%

Solution-State 2D NMR Spectroscopy of Plant Cell Walls Enabled by a Dimethylsulfoxide-d₆/1-Ethyl-3-methylimidazolium Acetate Solvent

et al. 2013

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Lignocellulosic biomass is composed of the polysaccharides cellulose and hemicellulose and the polyphenol lignin. Many current methods for analyzing the structure of lignocelluloses involve a sequential extraction of the material and subsequent analysis of the resulting fractions, which is labor-intensive and time-consuming. The work presented here assesses the dissolution of whole lignocellulosic material, focusing on biomass derived from the perennial bioenergy grass Miscanthus. The solvent dimethylsulfoxide (DMSO)-d6 containing 1-ethyl-3-methylimidazolium acetate ([Emim]OAc) was able to dissolve lignocellulosic material completely and gave high-resolution 2D heteronuclear single quantum coherence (HSQC) NMR spectra of the entire array of wall polymers. Extrapolated time-zero HSQC was applied using DMSO-d6/[Emim]OAc-d14 and enabled quantitative analysis of structural traits of lignocellulose components.

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Section: Resultsmentioning

confidence: 92%

Solution-State 2D NMR Spectroscopy of Plant Cell Walls Enabled by a Dimethylsulfoxide-d₆/1-Ethyl-3-methylimidazolium Acetate Solvent

et al. 2013

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“…The derivatives were based on the α-glucosidase inhibitor methyl acarviosin and the N -linked glycoside showed moderate inhibition of yeast α-glucosidase [85,86]. Cellotriose and cellotetraose derivatives were also synthesized where one of the rings had been replaced by a cyclohexene moiety, in efforts to mimic the sp 2 -hybridized transition state of cellulase hydrolysis [87]. The cyclohexene mimetics were indeed shown to effectively bind an endoglucanase (NCE5) from Humicola insolens and were observed to bind stronger than their native pyranose analogues.…”

Section: Replacement Of the Endocyclic O Atommentioning

confidence: 99%

Bioisosteres of Carbohydrate Functional Groups in Glycomimetic Design

Hevey

2019

Biomimetics

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The aberrant presentation of carbohydrates has been linked to a number of diseases, such as cancer metastasis and immune dysregulation. These altered glycan structures represent a target for novel therapies by modulating their associated interactions with neighboring cells and molecules. Although these interactions are highly specific, native carbohydrates are characterized by very low affinities and inherently poor pharmacokinetic properties. Glycomimetic compounds, which mimic the structure and function of native glycans, have been successful in producing molecules with improved pharmacokinetic (PK) and pharmacodynamic (PD) features. Several strategies have been developed for glycomimetic design such as ligand pre-organization or reducing polar surface area. A related approach to developing glycomimetics relies on the bioisosteric replacement of carbohydrate functional groups. These changes can offer improvements to both binding affinity (e.g., reduced desolvation costs, enhanced metal chelation) and pharmacokinetic parameters (e.g., improved oral bioavailability). Several examples of bioisosteric modifications to carbohydrates have been reported; this review aims to consolidate them and presents different possibilities for enhancing core interactions in glycomimetics.

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Role of the 4,6-O-acetal in the regio- and stereoselective conversion of 2,3-di-O-sulfonyl-β-d-galactopyranosides to d-idopyranosides

Hevey

Chen

Ling

2013

Carbohydrate Research

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Syntheses of cellotriose and cellotetraose analogues as transition state mimics for mechanistic studies of cellulases

Cited by 4 publications

References 31 publications

Solution-State 2D NMR Spectroscopy of Plant Cell Walls Enabled by a Dimethylsulfoxide-d₆/1-Ethyl-3-methylimidazolium Acetate Solvent

Solution-State 2D NMR Spectroscopy of Plant Cell Walls Enabled by a Dimethylsulfoxide-d₆/1-Ethyl-3-methylimidazolium Acetate Solvent

Bioisosteres of Carbohydrate Functional Groups in Glycomimetic Design

Role of the 4,6-O-acetal in the regio- and stereoselective conversion of 2,3-di-O-sulfonyl-β-d-galactopyranosides to d-idopyranosides

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Syntheses of cellotriose and cellotetraose analogues as transition state mimics for mechanistic studies of cellulases

Cited by 4 publications

References 31 publications

Solution-State 2D NMR Spectroscopy of Plant Cell Walls Enabled by a Dimethylsulfoxide-d6/1-Ethyl-3-methylimidazolium Acetate Solvent

Solution-State 2D NMR Spectroscopy of Plant Cell Walls Enabled by a Dimethylsulfoxide-d6/1-Ethyl-3-methylimidazolium Acetate Solvent

Bioisosteres of Carbohydrate Functional Groups in Glycomimetic Design

Role of the 4,6-O-acetal in the regio- and stereoselective conversion of 2,3-di-O-sulfonyl-β-d-galactopyranosides to d-idopyranosides

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Solution-State 2D NMR Spectroscopy of Plant Cell Walls Enabled by a Dimethylsulfoxide-d₆/1-Ethyl-3-methylimidazolium Acetate Solvent

Solution-State 2D NMR Spectroscopy of Plant Cell Walls Enabled by a Dimethylsulfoxide-d₆/1-Ethyl-3-methylimidazolium Acetate Solvent