Carbohydrate-Metal Complexes: Structural Chemistry of Stable Solution Species

Allscher, Thorsten; Klüfers, Peter; Mayer, Péter

doi:10.1007/978-3-540-30429-6_24

Cited by 17 publications

(17 citation statements)

References 168 publications

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“…This carbon shift was confirmed by 13 C NMR studies too [21]. However, molybdate can catalyze the epimerization of aldoses only in the pH range of 2.5-3.5, and the rate of epimerization drastically decreases with the increase in the pH [22]. In addition to this, being a homogeneous catalyst, its complete separation and recovery from the product mixture was found to be a difficult task.…”

Section: Introductionmentioning

confidence: 61%

“…Like molybdate, tungstate and vanadate also form glucose-metal complexes [22]. From NMR and DFT studies, it was shown that polyol molecules form a similar kind of complex with all these transition metal oxoanions [46,64,66].…”

Section: Comparison Of Catalytic Activities Of Mo W and Vmentioning

confidence: 98%

“…From NMR and DFT studies, it was shown that polyol molecules form a similar kind of complex with all these transition metal oxoanions [46,64,66]. The complex has an active binuclear metal centre, in which metal atoms are bridged by an oxygen atom and other coordinations are satisfied with 4 carbon atoms of the glucose, via oxygen atoms [22]. To understand and compare the catalytic performance of different transition metals (Mo, W, and V), we simulated the rate limiting 1,2 carbon shift for the epimerization of glucose.…”

Section: Comparison Of Catalytic Activities Of Mo W and Vmentioning

confidence: 98%

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First principles investigation into the metal catalysed 1,2 carbon shift reaction for the epimerization of sugars

Chethana

Lee

Mushrif

2015

Journal of Molecular Catalysis A: Chemical

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Section: Introductionmentioning

confidence: 61%

Section: Comparison Of Catalytic Activities Of Mo W and Vmentioning

confidence: 98%

Section: Comparison Of Catalytic Activities Of Mo W and Vmentioning

confidence: 98%

See 1 more Smart Citation

First principles investigation into the metal catalysed 1,2 carbon shift reaction for the epimerization of sugars

Chethana

Lee

Mushrif

2015

Journal of Molecular Catalysis A: Chemical

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“…The diols on the template must be separated from each other far enough to exclude the simultaneous formation of mixtures of 5- and 6-membered boronic esters. However, the oligosaccharides, which are available with a consistent oligomerization degree of dimer, trimer, tetramer and higher, are known to have only low tendencies of boronic ester formation [ 23 ]. Therefore, we turned to cis -dihydroxylated 5 , which exhibited a unique reactivity towards boronic acids because it forms two anellated cis -fused rings.…”

Section: Resultsmentioning

confidence: 99%

Assembly of synthetic Aβ miniamyloids on polyol templates

Fischer¹,

Geyer²

2015

Beilstein J. Org. Chem.

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SummaryCovalent dynamic chemistry is used to mimic the first steps of the highly cooperative fibril formation of Aβ peptides. For that purpose, Aβ peptide pentapeptide boronic acids 1 and 2 were synthesized by solid-phase peptide synthesis and studied in esterification experiments with polyhydroxylated templates. The bis-hydroxylated dipeptide Hot=Tap serves as a template of adjustable degree of oligomerization which spontaneously forms boronic esters with peptides of type 1 and 2. Nuclear magnetic resonance can differentiate between regioisomeric boronic esters and identifies preferred sites of esterification on the dimeric template 9. 2-Formylphenylboronic acid (14) is used to link the parent pentapeptide Leu-Val-Phe-Phe-Ala to the template 16 to obtain threefold boronic ester 17. The miniamyloid 17 assembles from seven components by imine and boronic ester bonds between the peptides and the template. The relative orientation and spacing of the peptides mimic the assembly of peptides in Alzheimer β-amyloids.

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“…Carboxylic acids and also the hydroxyl groups offer possible coordination sites. The metal complex formation mechanisms of sugar acids have been extensively reviewed (Allscher et al, 2008), therefore mechanistic considerations are left out of this review.…”

Section: Use Of Monomeric Sugar Acidsmentioning

confidence: 99%

Production and applications of carbohydrate-derived sugar acids as generic biobased chemicals

Mehtiö

Toivari

Wiebe

et al. 2015

Critical Reviews in Biotechnology

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This review considers the chemical and biotechnological synthesis of acids that are obtained by direct oxidation of mono- or oligosaccharide, referred to as sugar acids. It focuses on sugar acids which can be readily derived from plant biomass sources and their current and future applications. The three main classes of sugar acids are aldonic, aldaric and uronic acids. Interest in organic acids derived from sugars has recently increased, as part of the interest to develop biorefineries which produce not only biofuels, but also chemicals to replace those currently derived from petroleum. More than half of the most desirable biologically produced platform chemicals are organic acids. Currently, the only sugar acid with high commercial production is d-gluconic acid. However, other sugar acids such as d-glucaric and meso-galactaric acids are being produced at a lower scale. The sugar acids have application as sequestering agents and binders, corrosion inhibitors, biodegradable chelators for pharmaceuticals and pH regulators. There is also considerable interest in the use of these molecules in the production of synthetic polymers, including polyamides, polyesters and hydrogels. Further development of these sugar acids will lead to higher volume production of the appropriate sugar acids and will help support the next generation of biorefineries.

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Carbohydrate-Metal Complexes: Structural Chemistry of Stable Solution Species

Cited by 17 publications

References 168 publications

First principles investigation into the metal catalysed 1,2 carbon shift reaction for the epimerization of sugars

First principles investigation into the metal catalysed 1,2 carbon shift reaction for the epimerization of sugars

Assembly of synthetic Aβ miniamyloids on polyol templates

Production and applications of carbohydrate-derived sugar acids as generic biobased chemicals

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