- Reduction mechanism of tetrazolium salt XTT by a glucosamine derivative
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XTT (3′-{1-[(phenylamino)-carbonyl]-3,4-tetrazolium}-bis(methoxy-6- nitro)benzenesulfonic acid hydrate) was reduced by incubated glucosamine hydrochloride. The XTT reducibility by incubated glucosamine was linearly related with the DNA-breaking activity. In order to elucidate the reaction mechanism, the glucosamine derivatives formed during the incubation process were separated by HPLC, and the compound responsible for the reduction was analyzed. Among the incubated products, fructosazine and deoxyfructosazine were identified by LC-MS, FAB-MS, and 1H- and 13C-NMR. These products showed no XTT reducibility, but an unstable intermediate with a molecular weight of 322 displayed reducibility. Since the intermediate gave fructosazine by oxidation with XTT and was a precursor of deoxyfructosazine, we conclude that the intermediate could have been dihydrofructosazine. Therefore, the XTT reducibility by incubated glucosamine was based on dihydrofructosazine formed by the condensation of two molecules of glucosamine.
- Shimamura, Tomoko,Takamori, Atsuko,Ukeda, Hiroyuki,Sawamura, Masayoshi
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- Efficient one-pot synthesis of deoxyfructosazine and fructosazine from d-glucosamine hydrochloride using a basic ionic liquid as a dual solvent-catalyst
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An efficient one-pot dehydration process for convert d-glucosamine hydrochloride (GlcNH2) into 2-(d-arabino-1′,2′,3′,4′-tetrahydroxybutyl)-5-(d-erythro-2′′,3′′,4′′-trihydroxybutyl)pyrazine (deoxyfructosazine, DOF) and 2,5-bis-(d-arabino-1,2,3,4-tetrahydroxybutyl)pyrazine (fructosazine, FZ) was reported. A task-specific basic ionic liquid, 1-butyl-3-methylimidazolium hydroxide ([BMIM]OH), was employed as an environmentally-friendly solvent and catalyst. The products were qualitatively and quantitatively characterized by MALDI-TOF-MS, 1H NMR and 13C NMR spectroscopy. The influences of GlcNH2 concentrations, reaction temperature, reaction time, additives and co-solvents on the yields of products were studied. The maximum yield of 49% was obtained in the presence of [BMIM]OH and DMSO under optimized conditions (120 °C, 180 min). In addition, a plausible mechanism was proposed. Our project was to develop efficient, atom economical and eco-compatible routes for the synthesis of heterocyclic compounds from marine biomass (or nitrogen-containing biomass). The obtained aromatic heterocyclic compounds showed potential pharmacological action and physiological effects, and they also could be utilized as flavoring agents in the food industry. This journal is
- Jia, Lingyu,Wang, Yingxiong,Qiao, Yan,Qi, Yongqin,Hou, Xianglin
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- REACTION OF 2-AMINO-2-DEOXY-D-GLUCOSE AND LYSINE: ISOLATION AND CHARACTERIZATION OF 2,5-BIS(TETRAHYDROXYBUTYL)PYRAZINE
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The reaction of 2-amino-2-deoxy-D-glucose with lysine in water under simulated physiological conditions gave several browning products, with characteristic optical (λmax 340 nm) and fluorescent properties (emission at 430 nm for excitation at 362 nm).The major product was isolated and characterized by mass spectrometry and n.m.r. spectroscopy as 2,5-bis(tetrahydroxybutyl)pyrazine derived by the condensation of two molecules of 2-amino-2-deoxy-D-glucose.
- Candiano, Giovanni,Ghiggeri, Gian Marco,Gusmano, Rosanna,Zetta, Lucia,Benfenati, Emilio,Icardi, Giorgio
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- Preparation method and application of fructosazine
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The invention discloses a preparation method and application of fructozine, and the preparation method of the fructozine comprises the steps of synthesis of 1-dibenzylamino -1-deoxidized- D-fructose, preparation of 1-dibenzylamino- 1-deoxidized -4, 5-oxo- isopropylidene- D-fructose, preparation of isopropylidene protected fructozine and synthesis of the fructozine. According to the preparation method of the fructosazine, Pd/C is used for catalyzing amino sugar to be oxidized to form pyrazine rings for the first time. According to the reaction route, raw materials are economical and easy to obtain, reaction conditions are mild, high temperature and high pressure are avoided, the product is single and high in purity, and a complex post-treatment process is avoided. In addition, the invention provides application of the fructosazine in preparation of anti-aging cosmetics.
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Paragraph 0025; 0038-0039; 0053-0054
(2021/04/21)
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- Valorization of monosaccharides towards fructopyrazines in a new sustainable and efficient eutectic medium
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In this paper, we propose a new approach for valorization of monosaccharides derived from biomass into value added chemicals in a green and economically efficient manner by forming eutectic medium exclusively between reactants. Eutectic mixtures are emerging as an advantageous alternative to ionic liquids and have already found broad applications in biomass treatment; however they are preferably used only as low vapor pressure solvents. Increasing interest in eutectic solvents originates from their flexibility to adjust their properties to different biorefinery needs by simple variation of the compositions of eutectic mixtures. In this work, we made a first attempt to use a low molecular weight component, ammonium formate, to significantly change the physical properties of the eutectic mixtures and simultaneously increase their chemical reactivity. Using this approach, we valorised simple monosaccharides by turning them into fructopyrazines with high yields in their eutectic mixtures with ammonium formate. The research revealed a high sensitivity of the product yields to the temperature of the reaction and composition of the eutectic medium, as well as an important role of formate anions in product stabilization.
- Filonenko, Svitlana,Voelkel, Antje,Antonietti, Markus
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p. 5256 - 5266
(2019/10/11)
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- Method for preparing fructosazine by utilizing chitin-based biomass
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The invention relates to a method for preparing fructosazine by utilizing chitin-based biomass. The method comprises the following steps: adding a dry chitin-based biomass raw material, an imidazolium ionic liquid solution and an additive to dimethyl sulfoxide to obtain a mixture; uniformly mixing the obtained mixture to perform a reaction, wherein the mass ratio of the imidazolium ionic liquid to the chitin-based biomass raw material is 1: (2-100), and the mass ratio of the added chitin-based biomass raw material to an oxidant is 1: (1-50) to obtain an intermediate product; adding a crystallization solvent to the intermediate product, wherein the volume ratio of the intermediate product to the solvent is 1: 1 to 1: 10; completely dissolving the product; removing undissolved impurities to obtain a filter liquor; carrying out rotary evaporation concentration on the filter liquor; standing; and recrystallizing to prepare the final product. The method has the advantages of wide raw material resources, no pollution, simple preparation and high product purity.
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- 2,5-bis(tetrahydroxybutyl)pyrazines for the treatment of osteoarthritis and rheumatoid arthritis
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Use in the prevention and/or in the treatment of Osteoarthritis and Rheumatoid Arthritis of 2,5-Bis(tetrahydroxybutyl)pyrazines, compounds of formula (I), is disclosed. Compounds of the invention act simultaneously on cartilage matrix degradation and on nitric oxide and prostaglandin E2 production.
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Page/Page column 10
(2008/06/13)
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