5978-95-0Relevant academic research and scientific papers
D-idose, d-iduronic acid, and D-idonic acid from D-glucose via seven-carbon sugars
Liu, Zilei,Jenkinson, Sarah F.,Yoshihara, Akihide,Wormald, Mark R.,Izumori, Ken,Fleet, George W.J.
, (2019)
A practical synthesis of the very rare sugar d-idose and the stable building blocks for d-idose, d-iduronic, and d-idonic acids from ido-heptonic acid requires only isopropylidene protection, Shing silica gel-supported periodate cleavage of the C6-C7 bond of the heptonic acid, and selective reduction of C1 and/or C6. d-Idose is the most unstable of all the aldohexoses and a stable precursor which be stored and then converted under very mild conditions into d-idose is easily prepared.
D-Idose: A One- and Two-Dimensional NMR Investigation of Solution Composition and Conformation
Snyder, Joseph R.,Serianni, Anthony S.
, p. 2694 - 2702 (1986)
The solution composition of D-idose in D2O has been examined by 13C NMR spectroscopy using -enriched compounds.In addition to two furanoses and two pyranoses, aldehyde and hydrate forms have been detected and quantified.Using 13C saturation-transfer spectroscopy, unidirectional rate constants for ring-opening and -closing of idofuranoses and idopyranoses have been measured and compared.The 600-MHz 1H NMR spectrum of D-idose has been interpreted, and the 13C spectrum was assigned with the use of 2D 13C-1H shift correlation spectroscopy. 13C chemical shift assignments were confirmed with -enriched compounds. 1H-1H spin-spin couplings suggest the presence of skew forms of α-idopyranose.
A convenient synthesis of D-idose
Dromowicz, Manfred,Koell, Peter
, p. 169 - 171 (1998)
Addition of nitromethane to D-xylose leads to the formation of two epimeric deoxynitroalditols, namely 1-deoxy-1-nitro-D-iditol and 6-deoxy-6- nitro-L-glucitol. Conversion of the former, obtainable in good yield by direct crystallisation, by a modified Nef reaction in an argon atmosphere afforded 68% of D-idose, which may readily be converted into 1,6-anhydro-β- D-idopyranose ('D-idosan').
Orthogonal Active-Site Labels for Mixed-Linkage endo-β-Glucanases
Jain, Namrata,Tamura, Kazune,Déjean, Guillaume,Van Petegem, Filip,Brumer, Harry
, p. 1968 - 1984 (2021/05/26)
Small molecule irreversible inhibitors are valuable tools for determining catalytically important active-site residues and revealing key details of the specificity, structure, and function of glycoside hydrolases (GHs). β-glucans that contain backbone β(1,3) linkages are widespread in nature, e.g., mixed-linkage β(1,3)/β(1,4)-glucans in the cell walls of higher plants and β(1,3)glucans in yeasts and algae. Commensurate with this ubiquity, a large diversity of mixed-linkage endoglucanases (MLGases, EC 3.2.1.73) and endo-β(1,3)-glucanases (laminarinases, EC 3.2.1.39 and EC 3.2.1.6) have evolved to specifically hydrolyze these polysaccharides, respectively, in environmental niches including the human gut. To facilitate biochemical and structural analysis of these GHs, with a focus on MLGases, we present here the facile chemo-enzymatic synthesis of a library of active-site-directed enzyme inhibitors based on mixed-linkage oligosaccharide scaffolds and N-bromoacetylglycosylamine or 2-fluoro-2-deoxyglycoside warheads. The effectiveness and irreversibility of these inhibitors were tested with exemplar MLGases and an endo-β(1,3)-glucanase. Notably, determination of inhibitor-bound crystal structures of a human-gut microbial MLGase from Glycoside Hydrolase Family 16 revealed.
Anti-inflammatory active components of the roots of Datura metel
Qin, Ze,Zhang, Jin,Chen, Liang,Liu, Shu-Xiang,Zhao, Hai-Feng,Mao, Hui-Min,Zhang, Hong-Yang,Li, De-Fang
, p. 392 - 398 (2020/03/30)
One new phenolic glycoside, methyl 3,4-dihydroxyphenylacetate-4-O-[2-O-β-D-apisoyl-6-O-(2-hydroxybenzoyl)]-β-D-glucopyranoside (1), together with 10 known compounds (2–11), were isolated from the roots of Datura metel. The structures of these compounds we
Method for preparing lactic acid through catalytically converting carbohydrate
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Paragraph 0029-0040, (2020/11/01)
The invention relates to a method for preparing lactic acid through catalytically converting carbohydrate, and in particular, relates to a process for preparing lactic acid by catalytically convertingcarbohydrate under hydrothermal conditions. The method disclosed by the invention is characterized by specifically comprising the following steps: 1) adding carbohydrate and a catalyst into a closedhigh-pressure reaction kettle, and then adding pure water for mixing; 2) introducing nitrogen into the high-pressure reaction kettle to discharge air, introducing nitrogen of 2 MPa, stirring and heating to 160-300 DEG C, and carrying out reaction for 10-120 minutes; 3) putting the high-pressure reaction kettle in an ice-water bath, and cooling to room temperature; and 4) filtering the solution through a microporous filtering membrane to obtain the target product. The method can realize high conversion rate of carbohydrate and high yield of lactic acid, and has the advantages of less catalyst consumption, good circularity, small corrosion to reaction equipment and the like.
Formation of Chiral Structures in Photoinitiated Formose Reaction
Stovbun,Skoblin,Zanin,Tverdislov,Taran,Parmon
, p. 108 - 116 (2018/04/05)
The possibility to synthesize biologically important sugars and other chiral compounds without any initiators in the UV-initiated reaction of formaldehyde in aqueous solution has been shown for the first time. An optically active condensed phase due to an
13C-Labeled Idohexopyranosyl Rings: Effects of Methyl Glycosidation and C6 Oxidation on Ring Conformational Equilibria
Bose-Basu, Bidisha,Zhang, Wenhui,Kennedy, Jamie L. W.,Hadad, Matthew J.,Carmichael, Ian,Serianni, Anthony S.
, p. 1356 - 1370 (2017/02/10)
An ensemble of JHH, JCH, and JCC values was measured in aqueous solutions of methyl α- and β-d-idohexopyranosides containing selective 13C-enrichment at various carbons. By comparing these J-couplings to those reported previously in the α- and β-d-idohexopyranoses, methyl glycosidation was found to affect ring conformational equilibria, with the percentages of 4C1 forms based on 3JHH analysis as follows: α-d-idopyranose, methyl α-d-idopyranoside, methyl β-d-idopyranoside, β-d-idopyranose, 82%. JCH and JCC values were analyzed with assistance from theoretical values obtained from density functional theory (DFT) calculations. Linearized plots of the percentages of 4C1 against limiting JCH and JCC values in the chair forms were used to (a) determine the compatibility of the experimental JCH and JCC values with 4C1/1C4 ratios determined from JHH analysis and (b) determine the sensitivity of specific JCH and JCC values to ring conformation. Ring conformational equilibria for methyl idohexopyranosides differ significantly from those predicted from recent molecular dynamics (MD) simulations, indicating that equilibria determined by MD for ring configurations with energetically flat pseudorotational itineraries may not be quantitative. J-couplings in methyl α-l-[6-13C]idopyranosiduronic acid and methyl α-d-[6-13C]glucopyranosiduronic acid were measured as a function of solution pH. The ring conformational equilibrium is pH-dependent in the iduronic acid.
Shape-selective Valorization of Biomass-derived Glycolaldehyde using Tin-containing Zeolites
Tolborg, S?ren,Meier, Sebastian,Saravanamurugan, Shunmugavel,Fristrup, Peter,Taarning, Esben,Sádaba, Irantzu
, p. 3054 - 3061 (2016/11/17)
A highly selective self-condensation of glycolaldehyde to different C4 molecules has been achieved using Lewis acidic stannosilicate catalysts in water at moderate temperatures (40–100 °C). The medium-sized zeolite pores (10-membered ring framework) in Sn-MFI facilitate the formation of tetrose sugars while hindering consecutive aldol reactions leading to hexose sugars. High yields of tetrose sugars (74 %) with minor amounts of vinyl glycolic acid (VGA), an α-hydroxyacid, are obtained using Sn-MFI with selectivities towards C4 products reaching 97 %. Tin catalysts having large pores or no pore structure (Sn-Beta, Sn-MCM-41, Sn-SBA-15, tin chloride) led to lower selectivities for C4 sugars due to formation of hexose sugars. In the case of Sn-Beta, VGA is the main product (30 %), illustrating differences in selectivity of the Sn sites in the different frameworks. Under optimized conditions, GA can undergo further conversion, leading to yields of up to 44 % of VGA using Sn-MFI in water. The use of Sn-MFI offers multiple possibilities for valorization of biomass-derived GA in water under mild conditions selectively producing C4 molecules.
Catalytic effect of aluminium chloride on the example of the conversion of sugar model compounds
Schwiderski, Martin,Kruse, Andrea
, p. 64 - 70 (2015/04/14)
Abstract In this work, the catalytic effect of the Bronsted acid hydrochloric acid, the Bronsted base sodium hydroxide and the Lewis acid AlCl3 on the conversion of biomass derived carbohydrates is investigated. On the example of the glycolaldehyde conversion, it is shown that the Lewis acid catalyses the ketol-endiol-tautomerism, the dehydration, the retro-aldol-reaction and the benzilic-acid-rearrangement. The main products are C4- and C6-carbohydrates as well as their secondary products 2-hydroxybut-3-enoic acid 1 and several furans. Under the same reaction conditions hydrochloric acid catalyzes mainly the dehydration and sodium hydroxide the tautomerism and subsequent aldolization.
