Awesome and Easy Science Experiments about N-((2S,3R,4R,5R,6R)-2,4,5-Trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-3-yl)acetamide

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Design of glycosyltransferase inhibitors targeting human O-GlcNAc transferase (OGT)

Inhibition of glycosyltransferases requires the design of neutral inhibitors to allow cell permeation in contrast to their natural dianionic substrates. O-GlcNAc transferase (OGT) is a key enzyme involved in dynamic glycosylation of cytosolic and nuclear proteins in competition with phosphorylation. Designing OGT inhibitors is of prime interest for the better understanding of its biological implications. Introduction of a pyridine moiety as a pyrophosphate surrogate was evaluated, which provided moderate in vitro inhibition of OGT. Docking studies highlighted some key features for the binding of the designed inhibitors to the catalytic site of OGT where the carbohydrate moiety did not occupy its natural position but rather turned away and pointed to the solvent outside the catalytic pocket. Further investigation with cellular assays did not provide inhibition of OGT. This lack of OGT inhibition was rationalized with a permeation assay which revealed the sequestration of the inhibitors at the membrane. This journal is the Partner Organisations 2014.

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Reference:
Tetrahydropyran – Wikipedia,
Tetrahydropyran – an overview | ScienceDirect Topics

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Note that a catalyst decreases the activation energy for both the forward and the reverse reactions and hence accelerates both the forward and the reverse reactions.name: N-((2S,3R,4R,5R,6R)-2,4,5-Trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-3-yl)acetamide, you can also check out more blogs about14215-68-0

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Glycosynthase Principle Transformed into Biocatalytic Process Technology: Lacto- N-triose II Production with Engineered exo-Hexosaminidase

Glycosynthases are promising enzyme catalysts for glycoside synthesis. Derived from glycoside hydrolases by mechanistic repurposing of their active site, glycosynthases utilize suitably activated glycosyl donors for glycosylation, yet they are unable to hydrolyze the products thus formed. Although primed for synthetic application by their design, glycosynthases have yet to see actual use in carbohydrate production. To challenge limitations on glycosynthase applicability perceived from the process chemistry point of view, here we developed a glycosynthase (D746E variant) from Bifidobacterium bifidum beta-N-acetylhexosaminidase that is highly active synthetically (?100 mumol min-1 mg-1) and fully chemo- and regioselective when using N-acetyl-d-glucosamine 1,2-oxazoline for beta-1,3-glycosylation of lactose. We thus established a chemoenzymatic process technology for production of lacto-N-triose II, a core structural unit of human milk oligosaccharides. Using equivalent amounts of oxazoline (prepared chemically in 40% yield from N-acetyl-d-glucosamine) and lactose, we obtained lacto-N-triose II (515 mM; 281 mg mL-1 90% yield; ?1 h reaction time) immediately recoverable from the reaction in 85% purity. These metrics of process efficiency reveal the prodigious potential of the glycosynthase for trisaccharide production.

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Reference:
Tetrahydropyran – Wikipedia,
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Balanced chemical reaction does not necessarily reveal either the individual elementary reactions by which a reaction occurs or its rate law.Computed Properties of C8H15NO6. In my other articles, you can also check out more blogs about 14215-68-0

A catalyst don’t appear in the overall stoichiometry of the reaction it catalyzes, but it must appear in at least one of the elementary reactions in the mechanism for the catalyzed reaction. 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. In a Article,once mentioned of 14215-68-0, Computed Properties of C8H15NO6

Rational-Differential Design of Highly Specific Glycomimetic Ligands: Targeting DC-SIGN and Excluding Langerin Recognition

At the surface of dendritic cells, C-type lectin receptors (CLRs) allow the recognition of carbohydrate-based PAMPS or DAMPS (pathogen- or danger-associated molecular patterns, respectively) and promote immune response regulation. However, some CLRs are hijacked by viral and bacterial pathogens. Thus, the design of ligands able to target specifically one CLR, to either modulate an immune response or to inhibit a given infection mechanism, has great potential value in therapeutic design. A case study is the selective blocking of DC-SIGN, involved notably in HIV trans-infection of T lymphocytes, without interfering with langerin-mediated HIV clearance. This is a challenging task due to their overlapping carbohydrate specificity. Toward the rational design of DC-SIGN selective ligands, we performed a comparative affinity study between DC-SIGN and langerin with natural ligands. We found that GlcNAc is recognized by both CLRs; however, selective sulfation are shown to increase the selectivity in favor of langerin. With the combination of site-directed mutagenesis and X-ray structural analysis of the langerin/GlcNS6S complex, we highlighted that 6-sulfation of the carbohydrate ligand induced langerin specificity. Additionally, the K313 residue from langerin was identified as a critical feature of its binding site. Using a rational and a differential approach in the study of CLR binding sites, we designed, synthesized, and characterized a new glycomimetic, which is highly specific for DC-SIGN vs langerin. STD NMR, SPR, and ITC characterizations show that compound 7 conserved the overall binding mode of the natural disaccharide while possessing an improved affinity and a strict specificity for DC-SIGN.

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Reference:
Tetrahydropyran – Wikipedia,
Tetrahydropyran – an overview | ScienceDirect Topics

Archives for Chemistry Experiments of N-((2S,3R,4R,5R,6R)-2,4,5-Trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-3-yl)acetamide

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An efficient synthetic route to glycoamino acid building blocks for glycopeptide synthesis

(Chemical Equation Presented) Chemical glycopeptide synthesis requires access to gram quantities of glycosylated amino acid building blocks. Hence, the efficiency of synthesis of such building blocks is of great importance. Here, we report a fast and highly efficient synthetic route to Fmoc-protected asparaginyl glycosides from unprotected sugars in three steps with high yields. The glycosylated amino acids were successfully incorporated into target glycopeptides 7 and 8 by standard Fmoc solid-phase peptide synthesis.

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Reference:
Tetrahydropyran – Wikipedia,
Tetrahydropyran – an overview | ScienceDirect Topics

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Balanced chemical reaction does not necessarily reveal either the individual elementary reactions by which a reaction occurs or its rate law.Formula: C8H15NO6. In my other articles, you can also check out more blogs about 14215-68-0

A catalyst don’t appear in the overall stoichiometry of the reaction it catalyzes, but it must appear in at least one of the elementary reactions in the mechanism for the catalyzed reaction. 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. In a Article,once mentioned of 14215-68-0, Formula: C8H15NO6

Synthesis of Tc-99m labeled glucosamino-Asp-cyclic(Arg-Gly-Asp-d-Phe-Lys) as a potential angiogenesis imaging agent

Angiogenesis imaging agents for single photon emission computed tomography (SPECT) play a role in diagnosing tumor-induced angiogenesis as well as tumor metastasis. We synthesized and evaluated radiolabeled RGD glycopeptides by incorporation of the [99mTc(CO)3(H2O)3] +. 99mTc labeled glucosamino-D-c(RGDfK) ([99mTc]2) was prepared in 90-93% radiochemical yields (decay corrected). In vitro cell binding assays demonstrated selective binding [99mTc]2 to human umbilical vein endothelial (HUVE) cells, with inhibition of binding to 37.3% of control levels by 10 muM of cold authentic compounds. In addition, [99mTc]2 was shown to have high binding affinity to purified alphavbeta3 integrin (IC50 = 1.5 nM). These results suggest that these radiolabeled RGD glycopeptides may have value for non-invasive assessment of angiogenesis.

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Reference:
Tetrahydropyran – Wikipedia,
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I2/ionic liquid as a highly efficient catalyst for per-O-acetylation of sugar under microwave irradiation

A practical and highly efficient approach was developed to synthesize peracetylated sugar derivatives using a recyclable iodine/PEG400-based ionic liquid catalyst (I2/IL). The peracetylated sugars were readily obtained in a few minutes in excellent yields (90%-99%, 13 examples) on a multi-gram scale (50.0 mmol) by the reaction of sugar and acetic anhydride under microwave irradiation in the absence of a volatile organic solvent. The desired product was easily obtained by simple extraction with toluene from the reaction mixture, and I2/ILs can be readily recovered and reused at least six times without obvious loss in the yield. When the scale of the per-O-acetylation reaction was increased to 50.0 mmol, the desired product was still obtained in 90% yield after five recycles.

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Tetrahydropyran – Wikipedia,
Tetrahydropyran – an overview | ScienceDirect Topics

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Balanced chemical reaction does not necessarily reveal either the individual elementary reactions by which a reaction occurs or its rate law.category: Tetrahydropyrans. In my other articles, you can also check out more blogs about 14215-68-0

A catalyst don’t appear in the overall stoichiometry of the reaction it catalyzes, but it must appear in at least one of the elementary reactions in the mechanism for the catalyzed reaction. 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. In a Article,once mentioned of 14215-68-0, category: Tetrahydropyrans

4-METHYLUMBELLIFERYL 2-ACETAMIDO-2-DEOXY-alpha-D-GLUCOPYRANOSIDE, A FLUOROGENIC SUBSTRATE FOR N-ACETYL-alpha-D-GLUCOSAMINIDASE

Condensation of dimeric 3,4,6-tri-O-acetyl-2-deoxy-2-nitroso-alpha-D-glucopyranosyl chloride with 4-methylumbelliferone gave crystalline 4-methylumbelliferyl 3,4,6-tri-O-acetyl-2-deoxy-2-oximino-alpha-D-arabino-hexopyranoside.Acetylation of this adduct, reduction of the resulting crude O-acetyloxime with borane in oxolane, and acetylation gave the 3,4,6-tri-O-acetyl derivative of 4-methylumbelliferyl 2-acetamido-2-deoxy-alpha-D-glucopyranoside (1).A new sensitive assay of N-acetyl-alpha-D-glucosaminidase (EC 3.2.1.50) is made possible by fluorometric measurement of 4-methylumbelliferone liberated by enzymic hydrolysis of glycoside 1.Such assays are illustrated by results obtained with enzyme preparations from pig liver and human-blood serum.

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Tetrahydropyran – Wikipedia,
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Amide Cis-trans isomerization in aqueous solutions of methyl N -Formyl- d -glucosaminides and Methyl N -Acetyl- d -glucosaminides: Chemical equilibria and exchange kinetics

Amide cis-trans isomerization (CTI) in methyl 2-deoxy-2-acylamido-d- glucopyranosides was investigated by 1H and 13C NMR spectroscopy. Singly 13C-labeled methyl 2-deoxy-2-formamido-d- glucopyranoside (MeGlcNFm) anomers provided standard 1H and 13C chemical shifts and 1H-1H and 13C-13C spin-coupling constants for cis and trans amides that are detected readily in aqueous solution. Equipped with this information, doubly 13C-labeled methyl 2-deoxy-2-acetamido-d-glucopyranoside (MeGlcNAc) anomers were investigated, leading to the detection and quantification of cis and trans amides in this biologically important aminosugar. In comparison to MeGlcNFm anomers, the percentage of cis amide in aqueous solutions of MeGlcNAc anomers is small (?23% for MeGlcNFm versus ?1.8% for MeGlcNAc at 42 C) but nevertheless observable with assistance from 13C-labeling. Temperature studies gave thermodynamic parameters deltaG, deltaH, and deltaS for cis-trans interconversion in MeGlcNFm and MeGlcNAc anomers. Cis/trans equilibria depended on anomeric configuration, with solutions of alpha-anomers containing less cis amide than those of beta-anomers. Confirmation of the presence of cis amide in MeGlcNAc solutions derived from quantitative 13C saturation transfer measurements of CTI rate constants as a function of solution temperature, yielding activation parameters Eact, deltaG ?, deltaH-, and deltaS ? for saccharide CTI. Rate constants for the conversion of trans to cis amide in MeGlcNFm and MeGlcNAc anomers ranged from 0.02 to 3.59 s-1 over 31-85 C, compared to 0.24-80 s-1 for the conversion of cis to trans amide over the same temperature range. Energies of activation ranged from 16-19 and 19-20 kcal/mol for the cis ? trans and trans ? cis processes, respectively. Complementary DFT calculations on MeGlcNFm and MeGlcNAc model structures were conducted to evaluate the effects of an acyl side chain and anomeric structure, as well as C2-N2 bond rotation, on CTI energetics. These studies show that aqueous solutions of GlcNAc-containing structures contain measurable amounts of both cis and trans amides, which may influence their biological properties.

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Reference:
Tetrahydropyran – Wikipedia,
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Discovery of N-((2S,3R,4R,5R,6R)-2,4,5-Trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-3-yl)acetamide

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N-acetylglucosamine regulates morphogenesis and virulence pathways in fungi

N-acetylglucosamine (GlcNAc) is being increasingly recognized for its ability to stimulate cell signaling. This amino sugar is best known as a component of cell wall peptidoglycan in bacteria, cell wall chitin in fungi and parasites, exoskeletons of arthropods, and the extracellular matrix of animal cells. In addition to these structural roles, GlcNAc is now known to stimulate morphological and stress responses in a wide range of organisms. In fungi, the model organisms Saccharomyces cerevisiae and Schizosaccharomyces pombe lack the ability to respond to GlcNAc or catabolize it, so studies with the human pathogen Candida albicans have been providing new insights into the ability of GlcNAc to stimulate cellular responses. GlcNAc potently induces C. albicans to transition from budding to filamentous hyphal growth. It also promotes an epigenetic switch from White to Opaque cells, which differ in morphology, metabolism, and virulence properties. These studies have led to new discoveries, such as the identification of the first eukaryotic GlcNAc transporter. Other results have shown that GlcNAc can induce signaling in C. albicans in two ways. One is to act as a signaling molecule independent of its catabolism, and the other is that its catabolism can cause the alkalinization of the extracellular environment, which provides an additional stimulus to form hyphae. GlcNAc also induces the expression of virulence genes in the C. albicans, indicating it can influence pathogenesis. Therefore, this review will describe the recent advances in understanding the role of GlcNAc signaling pathways in regulating C. albicans morphogenesis and virulence.

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Tetrahydropyran – Wikipedia,
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Sequential One-Pot Multienzyme Chemoenzymatic Synthesis of Glycosphingolipid Glycans

Glycosphingolipids are a diverse family of biologically important glycolipids. In addition to variations on the lipid component, more than 300 glycosphingolipid glycans have been characterized. These glycans are directly involved in various molecular recognition events. Several naturally occurring sialic acid forms have been found in sialic acid-containing glycosphingolipids, namely gangliosides. However, ganglioside glycans containing less common sialic acid forms are currently not available. Herein, highly effective one-pot multienzyme (OPME) systems are used in sequential for high-yield and cost-effective production of glycosphingolipid glycans, including those containing different sialic acid forms such as N-acetylneuraminic acid (Neu5Ac), N-glycolylneuraminic acid (Neu5Gc), 2-keto-3-deoxy-d-glycero-d-galacto-nononic acid (Kdn), and 8-O-methyl-N-acetylneuraminic acid (Neu5Ac8OMe). A library of 64 structurally distinct glycosphingolipid glycans belonging to ganglio-series, lacto-/neolacto-series, and globo-/isoglobo-series glycosphingolipid glycans is constructed. These glycans are essential standards and invaluable probes for bioassays and biomedical studies.

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Reference:
Tetrahydropyran – Wikipedia,
Tetrahydropyran – an overview | ScienceDirect Topics