Chemical Properties and Facts of N-((2S,3R,4R,5R,6R)-2,4,5-Trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-3-yl)acetamide

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Owing to the expression of more than one type of galectin in animal tissues, the delineation of the functions of individual members of this lectin family requires the precise definition of their carbohydrate specificities. Thus, the binding properties of chicken liver galectin (CG-16) to glycoproteins (gps) and Streptococcus pneumoniae type 14 polysaccharide were studied by the biotin/avidin-mediated microtitre-plate lectin-binding assay and by the inhibition of lectin-glycan interactions with sugar ligands. Among 33 glycans tested for lectin binding, CG-16 reacted best with human blood group ABO (H) precursor gps and their equivalent gps, which contain a high density of D- galactopyranose(beta1-4)2-acetamido-2-deoxy-D-glucopyranose [Gal(beta1-4)GlcNAc] and Gal(beta1-3)GlcNAc residues at the non-reducing end, but this lectin reacted weakly or not at all with A-, H-type and sialylated gps. Among the oligosaccharides tested by the inhibition assay, the tri-antennary Gal(beta1-4)GlcNAc (Tri-II) was the best. It was 2.1 × 103 nM and 3.0 times more potent than Gal and Gal(beta1-4)GlcNAc (II)/Gal(beta1-3) GlcNAc(beta1-3)Gal(beta1-4)Glc (lacto-N-tetraose) respectively. CG-16 has a preference for the beta-anomer of Gal at the non-reducing end of oligosaccharides with a Gal(beta1-4) linkage > Gal(beta1-3) ? Gal(beta1-6). From the results, it can be concluded that the combining site of this agglutinin should be a cavity type, and that a hydrophobic interaction in the vicinity of the binding site for sugar accommodation increases the affinity. The binding site of CG-16 is as large as a tetrasaccharide of the beta-anomer of Gal, and is most complementary to lacto-N-tetraose and Gal(beta1-4)GlcNAc related sequences.

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Lapachol is a plant-derived naphthoquinone that kills several types of cancer cells. Derivatives of this molecule may therefore prove to be useful chemotherapeutic agents. In this study, we explored whether glycosylation increases the cytotoxic potency of lapachol towards HL-60 human leukemia cells. Two beta-glycosides were synthesized and characterized: LA4A (lapachol-beta-glucoside) and LA4C (lapachol-N-acetylglucosamine-beta-glucoside). The sugar moieties of both novel molecules were per-acetylated to facilitate cellular uptake. The IC50 values (in muM) for LA4A (5.7) and LA4C (5.3) were lower than those for lapachol (25). LA4A and LA4C triggered typical signs of apoptosis, such as the exposure of phosphatidylserine on the outside of cells, chromatin condensation, DNA fragmentation and a decrease of the mitochondrial transmembrane potential (DeltaPsim) prior to cell lysis. Moreover, DNA fragmentation triggered by the lapachol-glycosides was reduced by pre-treatment with the caspase inhibitor, z-VAD-fmk. While LA4A and LA4C activated caspases-3, -8 and -9, lapachol failed to activate these apoptotic proteases, even when used at high concentrations. Finally, the toxicity of lapachol and its derivatives was also tested on non-tumor cells. We used human peripheral neurons (PeriTox test) to evaluate the side effect potential of these compounds. LA4C was clearly less toxic than LA4A. We conclude that LA4C had the most favorable profile as drug candidate (high tumor cell toxicity, reduced neurotoxicity). In general, this study shows that the cytotoxicity of lapachol towards HL-60 can be enhanced by glycosylation, and that the therapeutic ratio may be modified by the type of sugar added.

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Neoglycosylations are increasingly being employed in the synthesis of natural products, drug candidates, glycopeptide mimics, oligosaccharide analogues, and other applications, but the efficiency of these reactions is usually limited by slow reaction times. Here, we show that aniline derivatives such as 2-amino-5-methoxybenzoic acid enhance the rate of acid-catalyzed neoglycosylation for a range of sugar substrates up to a factor of 32 relative to the uncatalyzed reaction.

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A facile, solvent-free acetylation method promoted by commercial 4A molecular sieves is described here for the synthesis of per-Oacetylated carbohydrates, which are important intermediates in carbohydrate chemistry. Several examples of carbohydrate and noncarbohydrate substrates are provided.

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Silica bromide as heterogeneous reagent is prepared from the reaction of silica gel with PBr3 as a nonhydroscopic, filterable, cheap, and stable yellowish powder that can be stored for months. The results show that the silica bromide is a suitable and efficient reagent for conversion of alcohols to alkyl bromides under mild conditions at room temperature. The easy availability of this reagent makes this simple procedure attractive and a practical alternative to the existing methods.

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Disclosed are quick dissolve tablets, each including Lactobacillus delbrueckii subsp bulgaricus (LBD) and N-acetyl-glucosamine (NAG), as well as excipients, for oral mucosal administration, for improving the quality of life of Hepatitis C patients. Any formulation suitable for oral mucosal administration can be employed for administering the active ingredients in a sufficient dosage for therapeutic effect, one such formulation being: 50 mg of Lactobacillus delbrueckii subsp bulgaricus lysate strain YB-I 10 mg of N-acetyl D-glucosamine. Excipients can include one or more of, maltodextrin; xanthan gum; acesulfam K; lemon powder and a flavoring, e.g., juice; Mannitol TL-32-04, Microcrystalline Cellulose and Carrageenan, Fructose, PVP-XL TL-11-04, Gellan Gum, Citrus TL 1-04, Orange TL 19-04, Sucrolose TL-13-04, and Mg ST TL-13-04.

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Preparation and use of synthetic monosaccharides, disaccharides, trisaccharides, tetrasaccharides and pentasaccharides useful for the preparation of synthetic heparinoids.

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Several alpha-L-Fuc-(1?3)-alpha-D-GlcNAcOC8H17 disaccharide derivatives bearing different hydroxylated alkyl chains, with or without sulfate groups at C-4 and/or C-6 positions of the GlcNAc unit, have been synthesized and tested as inhibitors of human astrocytoma lines U-373 and U-118. The antimitotic activity was dependent on the structure and position of the hydroxylated chain linked to the disaccharide. The compounds with a pentaerythritol or L-glyceryl chain at the C-6 position showed the best inhibitory properties, with an ID50 value of ca. 200 muM. On the contrary, sulfated disaccharide derivatives were inactive. The antimitotic activities of the compounds tested were essentially independent of the mitogen used to stimulate cell division.

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A class of novel sugar-based surfactants named alkoxyethyl 2-acetamido-2-deoxy-alpha-D-glucopyranosides were constructed by the introduction of oxyethene fragment (-OCH2CH2-) in the traditional alkyl glycoside structure. Such alkoxyethyl 2-acetamido-2-deoxy-alpha-D-glucopyranosides with different length of alkyl chain were synthesized, and their single configurations were confirmed to be alpha-anomer by 1H NMR and HRMS analysis. Their water solubility, surface tension, emulsification, foaming and thermal stability were investigated, and the effect of alkyl chain length on their surface property was also compared. The water solubility of alkoxyethyl 2-acetamido-2-deoxy-alpha-D-glucopyranoside was significantly superior to that of alkyl 2-acetamido-2-deoxy-alpha-D-glucopyranoside without an oxyethene fragment. Their dissolution process was an endothermic process and was driven by entropy increment as well. Alkoxyethyl 2-acetamido-2-deoxy-alpha-D-glucopyranoside was disclosed to reduce significantly the surface tension of water. For both of CMC and gammaCMC, there was a decreasing trend with increasing of alkyl chain length. As increasing of alkyl chain length, the maximum surface adsorption (Gammamax) increased and the molecular cross-sectional area (Amin) decreased. They adsorbed preferentially on the solution surface and then formed spontaneously micelles in solution by the hydrophobic effect. Nonyloxyethyl 2-acetamido-2-deoxy-alpha-D-glucopyranoside had the best foaming and emulsifying properties. All glycosides are thermally stable below 270 C. In view of the improvement of the water solubility and maintainance of surface activity with the introduction of the hydrophilic spacer, the novel alkoxyethyl 2-acetamido-2-deoxy-alpha-D-glucopyranoside should be expected to develop further its multiple applications as a class of novel water-soluble sugar-based surfactants in the future.

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In heterogeneous catalysis, the catalyst is in a different phase from the reactants. At least one of the reactants interacts with the solid surface in a physical process called adsorption in such a way. In an article, once mentioned the application of 14215-68-0, Name is N-((2S,3R,4R,5R,6R)-2,4,5-Trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-3-yl)acetamide,molecular formula is C8H15NO6, is a conventional compound. this article was the specific content is as follows.Application In Synthesis of N-((2S,3R,4R,5R,6R)-2,4,5-Trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-3-yl)acetamide

TNFR1-associated death domain protein (TRADD) with arginine N-GlcNAcylation is a novel and structurally unique posttranslational modification (PTM) glycoprotein that blocks the formation of death-inducing signaling complex (DISC), orchestrating host nuclear factor kappaB (NF-kappaB) signaling in entero-pathogenic Escherichia coli (EPEC)-infected cells. This particular glycosylated modification plays an extremely vital role for the effective colonization and pathogenesis of pathogens in the gut. Herein we describe the total synthesis of TRADD death domain (residues 195?312) with arginine235 N-GlcNAcylation (Arg-GlcNAc TRADD (195?312)). Two longish peptidyl fragments of the wild-type primary sequence were obtained by robust, microwave-assisted, highly efficient, solid-phase peptide synthesis (SPPS), the N-GlcNAcylated sector was built by total synthesis and attached specifically to resin-bound peptide with an unprotected ornithine residue via silver-promoted on-resin guanidinylation, Arg-GlcNAc TRADD (195?312) was constructed by hydrazide-based native chemical ligation (NCL). The facile synthetic strategy is expected to be generally applicable for the rapid synthesis of other proteins with Arg-GlcNAc modification and to pave the way for the related chemically biological study.

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