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Showing papers on "Aldose published in 2010"


Journal ArticleDOI
TL;DR: It is found that non-steroidal antiinflammatory N-phenylanthranilic acids, diclofenac and glycyrrhetic acid competitively inhibited AKR1B10, showing K(i) values of 0.35-2.9 microM and high selectivity to this enzyme (43-57 fold versus aldose reductase).
Abstract: A human aldose reductase-like protein, AKR1B10 in the aldo-keto reductase (AKR) superfamily, was recently identified as a tumor marker of several types of cancer. Tolrestat, an aldose reductase inhibitor (ARI), is known to be the most potent inhibitor of the enzyme. In this study, we compared the inhibitory effects of other ARIs including flavonoids on AKR1B10 and aldose reductase to evaluate their specificity. However, ARIs showed lower inhibitory potency for AKR1B10 than for aldose reductase. In the search for potent and selective inhibitors of AKR1B10 from other drugs used clinically, we found that non-steroidal antiinflammatory N-phenylanthranilic acids, diclofenac and glycyrrhetic acid competitively inhibited AKR1B10, showing K(i) values of 0.35-2.9 microM and high selectivity to this enzyme (43-57 fold versus aldose reductase). Molecular docking studies of mefenamic acid and glycyrrhetic acid in the AKR1B10-nicotinamide adenine dinucleotide phosphate (NADP(+)) complex and site-directed mutagenesis of the putative binding residues suggest that the side chain of Val301 and a hydrogen-bonding network among residues Val301, Gln114 and Ser304 are important for determining the inhibitory potency and selectivity of the non-steroidal antiinflammatory drugs. Thus, the potent and selective inhibition may be related to the cancer chemopreventive roles of the drugs, and their structural features may facilitate the design of new anti-cancer agents targeting AKR1B10.

51 citations


Journal ArticleDOI
TL;DR: The results suggest that the recombinant putative protein from Providencia stuartii will be useful as an industrial producer of D-lyxose, and the enzyme exhibited the highest activity for D-xylulose among all pentoses and hexoses.

25 citations


Journal ArticleDOI
TL;DR: It is demonstrated that certain kinds of Rh porphyrins on carbon black can electrochemically oxidize aldose at low potentials and involves 2-electron oxidation of the aldehyde group.

23 citations


Journal ArticleDOI
TL;DR: In this paper, Tetrabutylammonium bromide (TBAB, 10 mol%), in the molten state, efficiently catalyzes the reaction of a variety of in situ generated enamines, from arylamines and 1,3-ketones, with aldose sugars under solvent-free conditions.
Abstract: Readily available tetrabutylammonium bromide (TBAB, 10 mol%), in the molten state, efficiently catalyzes the reaction of a variety of in situ generated enamines, from arylamines and 1,3-ketones, with aldose sugars under solvent-free conditions. The reaction proceeds rapidly and affords the corresponding protected annulated pyrrole derivatives in good to high yields (55-78%) after acetylation. The present methodology offers advantages such as excellent yields, a simple procedure, shorter reaction times, and milder conditions.

13 citations


Journal ArticleDOI
TL;DR: New substituted aroylhydrazones (4a-f) were synthesized from the acid hydrazide and the corresponding aldehyde or aldose and showed moderate to high inhibition activities.
Abstract: New substituted aroylhydrazones (4a-f) were synthesized from the acid hydrazide (3) and the corresponding aldehyde or aldose. 5-Amino-4-cyano-1H-pyrazole derivatives (6a-f) were prepared by the reaction of the aroylhydrazones (4a-f) with malononitrile. The synthesized compounds were tested for antimicrobial activity against various bacteria and fungi and showed moderate to high inhibition activities. Compounds incorporating a sugar moiety as well as a pyrazolyl ring in their structure displayed the highest antimicrobial activity.

12 citations


Journal ArticleDOI
TL;DR: In this paper, a branched-chain aldose bearing an azido group at the C-2 position provides access to the corresponding 1-deoxy-1-azido- and 1 -deoxy -1-amino ketoses in a single step via stereospecific isomerization.
Abstract: A branched-chain aldose bearing an azido group at the C-2 position provides access to the corresponding 1-deoxy-1-azido- and 1-deoxy-1-amino ketoses in a single step via stereospecific isomerization. The isomerization exploited the catalytic effect of molybdate ions and microwave irradiation. The structures of the products were analyzed by NMR spectroscopy, IR, HRMS spectrometry and quantum-chemical DFT calculations. DFT-computed proton-proton coupling constants of the prepared Amadori ketose 1-deoxy-1-amino- d - gluco -heptulose were found to be comparable with the experimentally obtained coupling constants and were in agreement with the 4 C 1 pyranose form in aqueous solution at room temperature.

8 citations


Journal ArticleDOI
TL;DR: In this article, the structure of condensation products of 2-hydroxy- and 2-sulfanylbenzohydrazides with a series of aldoses was studied by 1H and 13C NMR spectroscopy.
Abstract: The structure of the condensation products of 2-hydroxy- and 2-sulfanylbenzohydrazides with a series of aldoses (L-arabinose, D-ribose, L-ramnose, D-galactose, D-glucose, D-mannose) was studied by 1H and 13C NMR spectroscopy. The condensation products of monosaccharides with 2-hydroxybenzohydrazide in DMSO-d6 solution exist as equilibrium mixtures of linear hydrazone and cyclic pyranose and furanose forms, the cyclic tautomers being represented by two stereoisomers (α- and β-anomers). The aldose condensation products with 2-sulfanylbenzohydrazide in the crystalline state have cyclic 1,3,4-benzothiadiazepine structure, while in DMSO-d6 solution they undergo complete or partial isomerization into cyclic pyranose tautomer.

7 citations


Journal ArticleDOI
TL;DR: An extension of the halogenation of 1,2 or 1,3-diols via a cyclic thionocarbonate functionality by reaction with an allyl halide instead of methyl iodide, which is usually used.

4 citations


Patent
15 Sep 2010
TL;DR: In this paper, a color development method for phosphate ions contained in an inspection water was proposed, which includes a step in which a first water solution containing hexaammonium heptamolybdate or alkali metal salts of molyb date, an antimony compound with a valence of antimony of 3 such as tartrate antimonylcalium and sulfate and a second water solution including saccharide compounds selected from the group of monosaccharides such as aldose with carbon number of 5, aldoses with carbon numbers of
Abstract: PROBLEM TO BE SOLVED: To develop the color of phosphate ions contained in an inspection water through generation of molybdenum blue by means of an agent which can be stored.SOLUTION: A color development method for phosphate ions contained in an inspection water includes a step in which a first water solution containing hexaammonium heptamolybdate or alkali metal salts of molybdate, an antimony compound with a valence of antimony of 3 such as tartrate antimonylcalium and sulfate and a second water solution including saccharide compounds selected from the group of monosaccharide compounds such as aldose with carbon number of 5, aldose with carbon number of 6, ketose with carbon number of 6 and oligosaccharide or glycoside which can produce one of these monosaccharides through decomposition are added to inspection water and a step in which the inspection water to which the first water solution and the second water solution are added is heated to 60°C or more.

1 citations


Patent
15 Feb 2010
TL;DR: In this article, an independent claim is also included for adjusting the viscosity, color and flavor using the ready systems (mixtures of at least two components with the manufactured product) and is combined depending upon the application and the customer request.
Abstract: Producing flavor and color giving food ingredients, comprises reacting an aldose and/or a ketose with at least one free amino group of food ingredients without adding additional reaction accelerators. The obtained food ingredient does not require a special labeling by E-number (number codes for food additives). An independent claim is also included for adjusting the viscosity, color and flavor using the ready systems (mixtures of at least two components with the manufactured product) and is combined depending upon the application and the customer request.

Journal ArticleDOI
TL;DR: In this article, it was shown that the photoreduction of 3-deoxy glycopyranosid-4ulosides, derived from carbohydrates, results in selective Ca-0 bond cleavage.
Abstract: 3-Deoxyaldos-4-uloses are suitable synthons in the synthesis of various natural products and analogues containing chiral diol subunits [l]. Moreover, 3,6-dideoxyhexoses are found in many biologically important compounds, for instance in lipopolysaccharides, conferring on them their serological specificity [2]. A general synthetic approach to these sugars involves the stereoselective reduction of aldose derived epoxides [3]. Alternatively they have been prepared from furfuryl aIcohols [4] by deamination of methyl 3-amino-3-deoxy-P-o-allopyranoside [5] or from methyl 4,6-0-benzylidene-3-deoxy-~-o-ti~o-hexopyranoside [6] in modest yields. In connection with our studies [7] on the chemistry of radical-anions produced photochemically by electron transfer from triethylamine onto carbonyl compounds, we have found that the photoreduction of @-epoxyketones, derived from carbohydrates, results in selective Ca-0 bond cleavage. This allows us to report here an efficient synthesis of alkyl 3-deoxyglycopyranosid-4-ulosides (Scheme 1). Furthermore, by using this methodology, a short synthesis of the methyl glycoside of cinerulose B, a rare sugar [8] present in the antibiotic Cinerubine B, has been achieved (Scheme 2). The epoxyketones ( >-2 and ( + j-2 were obtained by Swern oxidation of methyl 2,3-anhydro-p-L-ribopyranoside 191 ( j-1 and of methyl 2,3-anhydro-P-oribopyranoside [9] ( + >-1, respectively. Epoxyketone ( + )-5 was obtained by alkaline hydrogen peroxide oxidation of enone [lo] ( + )-4. The regiospecific ring opening of

Patent
30 Jul 2010
TL;DR: In this article, the authors determined the total phosphorous quantity in test water safely and in a short time period by breaking down phosphorous compounds and converting to phosphate ions, and then determining the quantity of phosphate ions in the test water.
Abstract: The disclosed method determines the total phosphorous quantity in test water safely and in a short time period by breaking down phosphorous compounds included in test water and converting to phosphate ions, and then determining the quantity of phosphate ions in the test water In the method, first sulfuric acid and alkali metal salts of peroxodisulfuric acid are added to test water, and the mixture is heated for a prescribed time period at a temperature from 65˚C to boiling temperature An aqueous solution is added to the test water, said aqueous solution containing at least one hydroxyl group-containing compound selected from the hydroxyl group-containing compound group consisting of hydroxyl carboxylic acids and alditol, a vanadium compound having a vanadium valence of 3-5, a non-reducing oligosaccharide capable of generating a 5 carbon aldose, a 6 carbon aldose or a 6 carbon ketose by means of decomposition, 7-molybdic acid 6-ammonium, and an antimony compound wherein the antimony valence is 3, and after heating the test water to at least 65˚C for a prescribed time period, the light absorbance of the test water for an arbitrary wavelength occurring in the range of 600-950nm is measured