Final Thoughts on Chemistry for N-((2S,3R,4R,5R,6R)-2,4,5-Trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-3-yl)acetamide

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A series of alpha2-3-sialylated beta1-3-linked galactosides, including sialyl T-antigens, 3?-sialyl galacto-N-biose, 3?-sialyl lacto-N-biose, and their derivatives containing natural and non-natural sialic acid forms have been synthesized from simple monosaccharides using an efficient sequential two-step multienzyme approach.

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Tetrahydropyran – Wikipedia,
Tetrahydropyran – an overview | ScienceDirect Topics

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

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Sialic acids (Sias) are important constituents of cell surface glycans. Ready access to Sias in large quantities would facilitate the development of carbohydrate-based vaccines and small-molecule drugs. We now present a facile method for synthesizing various natural forms and non-natural derivatives or analogs of Sias by using a whole-cell catalyst, which is constructed by adding a plasmid containing necessary enzyme genes into a metabolically engineered strain of Escherichia coli. The flexible substrate tolerance of incorporated enzymes (N-acetylglucosamine 2-epimerase and N-acetylneuraminic acid aldolase) allows the cellular catalyst to convert a wide range of simple and inexpensive sugars into various Sia-related compounds through an easily scalable fermentation process. Further, syntheses using this whole-cell biotransformation in combination with three conventional enzymatic reactions provide a series of complex Sia-containing glycans (sialyloligosaccharides) and their derivatives bearing different substituents. The processes described herein should permit the large-scale and economical production of both Sias and sialyloligosaccharides, and may complement existing chemical and enzymatic strategies.

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Tetrahydropyran – Wikipedia,
Tetrahydropyran – an overview | ScienceDirect Topics

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The rice blast fungus Magnaporthe oryzae’s genome encodes a hypothetical protein (MGG-03307) containing a type III CVNH lectin, in which a LysM domain is inserted between individual repeats of a single CVNH domain. At present, no structural or ligand binding data are available for any type III CVNH and functional studies in natural source organisms are scarce. Here, we report NMR solution structure and functional data on MGG-03307. The structure of the CVNH/LysM module revealed that intact and functionally competent CVNH and LysM domains are present. Using NMR titrations, carbohydrate specificities for both domains were determined, and it was found that each domain behaves as an isolated unit without any interdomain communication. Furthermore, live-cell imaging revealed a predominant localization of MGG-03307 within the appressorium, the specialized fungal cell for gaining entry into rice tissue. Our results suggest that MGG-03307 plays a role in the early stages of plant infection.

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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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Triazole linked heparosan and chondroitin disaccharide and tetrasaccharide building blocks were synthesized in a stereoselective manner by applying a very efficient copper catalyzed azide-alkyne cycloaddition (CuAAC) reaction of appropriately substituted azido-glucuronic acid and propargyluted N-acetyl glucosamine and N-acetyl galactosamine derivative, respectively. The resulting suitably substituted tetrasaccharide analogues can be easily converted into azide and alkyne unit for further synthesis of higher oligosaccharide analogues.

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Tetrahydropyran – Wikipedia,
Tetrahydropyran – an overview | ScienceDirect Topics

Extracurricular laboratory:new discovery of N-((2S,3R,4R,5R,6R)-2,4,5-Trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-3-yl)acetamide

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A short and high-yielding synthesis has been devised to prepare C-linked 2-deoxy-2-acetamido-alpha-D-galactopyranose derivative 3. One of the main advantages of this approach is that it employs commercially available and inexpensive D-glucosamine as the starting material. The key steps include a highly stereoselective C-allylation followed by epimerization of the C-4 hydroxyl group. Building block 3 and orthogonally protected C-linked 2-deoxy-2-acetamido-alpha-D-galactopyranose derivative 2 were obtained in 44% overall yield (six steps) and 29% overall yield (eight steps), respectively. This represents a significant improvement over previously reported syntheses.

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Tetrahydropyran – Wikipedia,
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The present invention relates to a method for preparing a sialic acid derivative, wherein the method is characterized in that a process of using N-acetyl-D-glucosamine to prepare CMP-M-acetylneuraminic acid and a process of combining sialic acid with galactose or a galactose derivative to prepare a sialic acid (neuraminic acid) derivative are performed together in one reactor. According to the present invention, a high-priced cytidine 5′-monophosphoric acid (CMP) can be recycled in a reaction container, thereby reducing the amount of cytidine 5′-monophosphoric acid (CMP) introduced into the reaction, producing a sialic acid derivative using low-priced N-acetyl-D-glucosamine and pyruvic acid as substrates, and producing the sialic acid derivative at higher efficiency.

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Tetrahydropyran – Wikipedia,
Tetrahydropyran – an overview | ScienceDirect Topics

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Promiscuous galactokinases (GalKs), which catalyse the ATP dependent phosphorylation of galactose in nature, have been widely exploited in biotechnology for the rapid synthesis of diverse sugar-1-phosphates. This work focuses on the characterisation of a bacterial GalK from Streptomyces coelicolor (ScGalK), which was overproduced in Escherichia coli and shown to phosphorylate galactose. ScGalK displayed a broad substrate tolerance, with activity towards Gal, GalN, Gal3D, GalNAc, Man and L-Ara. Most interestingly, ScGalK demonstrated a high activity over a broad pH and temperature range, suggesting that the enzyme could be highly amenable to multi-enzyme systems.

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Reference£º
Tetrahydropyran – Wikipedia,
Tetrahydropyran – an overview | ScienceDirect Topics

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Selective halogenation of 2-amino-2-deoxy-D-glycopyranoses on C-6

N-protected 2-amino-2-deoxy-D-glycopyranoses can be selectively halogenated on C-6 by treatment with triphenylphosphine-carbone tetrahalide-pyridine.

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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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A synthetic approach to aromatic aminoglycoside as a neamine mimic

This paper describes the synthetic approach to an aromatic a-glycoside as a mimic of neamine, which is a common core structure of some aminoglycoside antibiotics. We achieved the synthesis of the protected precursor of the neamine mimic, 4-(2,6-diamino-2,6-dideoxy-alpha-D-glucopyranosyloxy)-1,3- phenylenediamine, from N-acetyl-D-glucosamine and 2,4-diaminophenol as the starting materials using a glycosylation technique.

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Reference£º
Tetrahydropyran – Wikipedia,
Tetrahydropyran – an overview | ScienceDirect Topics

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The reaction rate of a catalyzed reaction is faster than the reaction rate of the uncatalyzed reaction at the same temperature.31608-22-7, Name is 2-(4-Bromobutoxy)tetrahydro-2H-pyran, molecular formula is C9H17BrO2. In a Article£¬once mentioned of 31608-22-7, category: Tetrahydropyrans

Photophysical properties of the ReI and RuII complexes of a new C60-substituted bipyridine ligand

The rhenium(I) and ruthenium(II) complexes of a fullerene-substituted bipyridine ligand have been prepared. Electrochemical studies indicate that some ground state electronic interaction between the fullerene subunit and the metal-complexed moiety are present in the ReI but not the RuII complex. The photophysical properties have been investigated by steady-state and time-resolved UV/Vis-NIR luminescence spectroscopy and nanosecond laser flash photolysis in CH2Cl2 solution, and compared to those of the corresponding model compounds. Excitation of the methanofullerene moiety in the dyads does not lead to excited state intercomponent interactions. Instead, excitation of the metal-complexed unit shows that the lowest triplet metal-to-ligand-charge-transfer excited state (3MLCT) centered on the ReI- or RuIItype unit is quenched with a rate constant of about 2.5 ¡Á 108 s-1. The quenching is attributed to an electron-transfer (E1T) process leading to the reduction of the carbon sphere, as determined by luminescence spectroscopy for the RuII dyad. Experimental detection of electron transfer in the ReI dyad is prevented due to the unfavorable absorption of the metal-complexed moiety relative to the fullerene unit. However, it can be postulated on the basis of energetic/kinetic arguments and by comparison with the RuII-type array. The primary E1T process is followed by charge-recombination to give the lowest-lying fullerene triplet excited state (3C60) with quantitative yield, as determined by sensitized singlet oxygen luminescence experiments. Direct 3MLCT ? 3C60 triplet-triplet energy-transfer (EnT) does not successfully compete with E1T since it is highly exoergonic and located in the Marcus inverted region. The quantum yield of singlet oxygen sensitization (phiDelta) of the RuI-based dyad is found to be lower (0.80) than for the corresponding RuII derivative (1.0). This is likely to be the consequence of different conformational structures for the two dyads, rather than a different yield of 3C60 formation.

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Tetrahydropyran – Wikipedia,
Tetrahydropyran – an overview | ScienceDirect Topics