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13C NMR relaxation studies on cartilage and cartilage components

We have investigated the molecular motions of polysaccharides of bovine nasal and pig articular cartilage by measuring the 13C NMR relaxation times (T1 and T2). Both types of cartilage differ significantly towards their collagen/glycosaminoglycan ratio, leading to different NMR spectra. As chondroitin sulfate is the main constituent of cartilage, aqueous solutions of related poly- and monosaccharides (N-acetylglucosamine and glucuronic acid) were also investigated. Although there are only slight differences in T1 relaxation of the mono- and the polysaccharides, T2 decreases about one order of magnitude, when glucuronic acid or N-acetylglucosamine and chondroitin sulfate are compared. It is concluded that the ring carbons are motion-restricted primarily by the embedment in the rigid pyranose structure and, thus, additional limitations of mobility do not more show a major effect. Significant differences were observed between bovine nasal and pig articular cartilage, resulting in a considerable line-broadening and a lower signal to noise ratio in the spectra of pig articular cartilage. This is most likely caused by the higher collagen content of articular cartilage in comparison to the polysaccharide-rich bovine nasal cartilage. Copyright (C) 2000 Elsevier Science Ltd.

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Tetrahydropyran – Wikipedia,
Tetrahydropyran – an overview | ScienceDirect Topics

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Design of alpha-transglucosidases of controlled specificity for programmed chemoenzymatic synthesis of antigenic oligosaccharides

Combined with chemical synthesis, the use of biocatalysts holds great potential to open the way to novel molecular diversity. We report in vitrochemoenzymatic pathways that, for the first time, take advantage of enz yme engineering to produce complex microbial cell-surface oligosaccharides and circumvent the chemical boundaries of glycochemistry. Glycoenzymes were designed to act on nonnatural conveniently protected substrates to produce intermediates compatible with a programmed chemical elongation. The study was focused on the synthesis of oligosaccharides mimicking the O-antigen motif of Shigella flexneri serotypes 1b and 3a, which couldbe used for the development of multivalent carbohydratebased vaccines. A semirational engineering approach was successfully applied to amylosuc rase, a transglucosidase that uses a low cost sucrose substrate as a glucosyl donor. The main difficulty was to retain the enzyme specificity toward sucrose, while creating a new catalytic function to render the enzyme able to regiospecifically glucosylate protected nonnatural acceptors.A structurally guided library of 133 mutants was generated from which s everal mutants with either completely new specificity toward methyl alpha-L-rhamnopyranoside or a tremendously enhanced one toward allyl 2-acetamido-2-deoxy-alpha-D-glucopyranoside acceptors were isolated. The best variants were used to synthesize glucosylated building blocks. They were then converted into acceptors and potential donors compatible with chemical elongation toward oligosaccharide fragments of the O-antigens ofthe two targeted serotypes. This is the first report of a successful en gineering of an alpha-transglycosidase acceptor binding site that led to new specificities. It demonstrates the potential of appropriate combinations of a planned chemoenzymatic pathway and enzyme engineering in glycochemistry.

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Tetrahydropyran – Wikipedia,
Tetrahydropyran – an overview | ScienceDirect Topics

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A galactose-specific lectin from the red marine alga Ptilota filicina

A lectin from the red marine alga Ptilota filicina (PFL) was isolated by affinity chromatography on cross-linked guar gum. PFL agglutinated native and papain-treated human erythrocytes with preference for type O erythrocytes. The lectin was inhibited by galactose and its derivatives. The most potent inhibitors were p-Nitrophenyl-N-acetyl-alpha-and beta-D-galactosaminide. Porcine stomach mucin, bovine submaxillary gland mucin and asialo bovine mucin were also inhibitory. The M(r) of PFL, determined by gel filtration, was 56,900. SDS-PAGE gave one band with a subunit M(r) of 19,320, indicating the native protein to be a trimer of apparently identical subunits. PFL was shown to be rich in acidic and hydroxyl amino acids but low in basic amino acids. The ten N-terminal amino acids were Asx-Thr-Lys-Thr-Tyr-Leu-Leu-Ala-.

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Tetrahydropyran – Wikipedia,
Tetrahydropyran – an overview | ScienceDirect Topics

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Synthesis and characterization of monosaccharide derivatives and application of sugar-based prolinamides in asymmetric synthesis

For the first time, the beta-anomer of N-acetylglucosamine derivative methyl 2-acetamido-3,4,6-tri-O-benzyl-2-deoxy-beta-D-glucopyranoside (9b) was synthesized, isolated, and used in the synthesis of sugar-based primary amine 4b. Sugar-based primary amine 5a, an anomeric pair of monosaccharide derivatives 6a and 6b, and precursors to all these compounds were also synthesized, isolated, and well studied by standard spectroscopic methods, including 2D NMR spectroscopy experiments such as 1H-1H COSY and HSQC. Then sugar-based primary amines 4a, 5a, 6a, and 6b were converted into the corresponding prolinamide organocatalysts (i.e., 1a, 2a, 3a, and 3b) in high yields. The catalytic activity of these sugar-based prolinamide organocatalysts was demonstrated in asymmetric aldol reactions in various solvents and at different temperatures. The oraganocatalyst 3a was shown to be an efficient and powerful organocatalyst for the enantioselective aldol reaction of various cyclic or acyclic ketones with aromatic aldehydes in a mild and facile reaction, which gave the corresponding aldol adducts with high levels of diastereoselectivity (up to 99:1) and enantioselectivity (up to >99 %) in almost all cases.

The reactant in an enzyme-catalyzed reaction is called a substrate. Enzyme inhibitors cause a decrease in the reaction rate of an enzyme-catalyzed reaction.I hope my blog about 14215-68-0 is helpful to your research., category: Tetrahydropyrans

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Tetrahydropyran – Wikipedia,
Tetrahydropyran – an overview | ScienceDirect Topics

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Direct glycosylation of unprotected and unactivated sugars using bismuth nitrate pentahydrate

Bi(NO3)3, a low-cost, mild, and environmentally green catalyst, has been successfully utilized for Fischer glycosylation for the synthesis of alkyl/aryl glycopyranosides by reacting unprotected sugars, namely, D-glucose, L-rhamnose, D-galactose, D-arabinose, and N-acetyl-D-glucosamine with various alcohols in good to excellent yields. The glycosides were formed with high alpha-selectivity. Further, an expedient separation of alpha- and beta-glycosides using silver nitrate-impregnated silica gel flash liquid chromatography has been developed.

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Tetrahydropyran – Wikipedia,
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Characterization and inhibitor studies of chitinases from a parasitic blowfly (Lucilia cuprina), a tick (Boophilus microplus), an intestinal nematode (Haemonchus contortus) and a bean (Phaseolus vulgaris)

The molecular weight pattern and the stage-specific activities of chitinases from the blowfly Lucilia cuprina, the tick Boophilus microplus and the intestinal nematode Haemonchus contortus were examined. Chitinolytic enzymes could be detected in all parasite species tested, but the activity was different between the stages. Highest chitinolytic titers were found in blowfly pupae (83 kDa, 118 kDa), hatching larvae of ticks (58 kDa, 94 kDa) and nematode eggs (43 kDa). Leaves from ethylene-treated bean plants Phaseolus vulgaris expressed two basic Class I chitinases (Ia, Ib) of 34 kDa, differing in their amino acid sequences at residue 33 and 34 (Ia: glycine, proline; Ib: lysine, aspartic acid). Inhibitor studies with blowfly pupae revealed that allosamidin (IC50 = 0.32 (¡À0.02) muM) was by far the best inhibitor when compared with various amino sugar derivatives. This compound also inhibited chitinases from tick larvae (IC50 = 0.69(¡À0.10) muM) and nematode eggs (IC50 = 0.048(¡À0.0045) muM) specifically. Whereas Class Ia chitinase from bean leaves was inhibited only up to 18% by 10 muM allosamidin, it had an IC50 of 1(¡À0.14) muM for the Ib type, which is the first plant chitinase described to be highly sensitive to allosamidin.

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Tetrahydropyran – Wikipedia,
Tetrahydropyran – an overview | ScienceDirect Topics

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CARBOHYDRATE-BINDING SPECIFICITY OF SILKWORM LECTIN

The binding specificity of a lectin from the hemolymph of silkworm larvae was examined quantitatively by taking advantage of the fluorospectrophotometric properties of the lectin.On excitation at 280 nm, the lectin fraction gave a fluorescence-emission spectrum centered at 336 nm, which was attributable to tryptophan residues.The fluorescence could be completely quenched by the addition of specific saccharides.The affinity constants of the silkworm lectin with specific saccharides were calculated from the changes in intensities of fluorescence-difference spectra induced by the saccharides.The silkworm lectin had the highest affinity for dermatan sulfate and hyaluronic acid, followed by protuberic acid, heparin, and chondroitin sulfate A.Among monosaccharides tested, only D-glucuronic acid and N-acetylneuraminic acid induced weak but significant quenching, and their affinity constants were found to be low.These results indicate that the silkworm lectin has a strong affinity for carboxyl groups, especially alpha-L-iduronic acid residues, in the saccharides.In most cases, sulfate groups on the saccharides interfere with the specific interactions.

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Tetrahydropyran – Wikipedia,
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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, belongs to Tetrahydropyrans compound, is a common compound. In a patnet, once mentioned the new application about 14215-68-0, COA of Formula: C8H15NO6

A Mild Procedure for the Preparation of 1,6-Anhydro-beta-D-hexopyranoses and Derivatives

Treatment of reducing 6-O-tosyl-D-glucopyranoses 1 with 1,8-diazabicyclo<5.4.0>undec-7-ene (DBU) afforded the corresponding 1,6-anhydro-beta-D-hexopyranoses 2 in high yields.Reaction was also performed on partly acetylated tosylates of carbohydrates.

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Tetrahydropyran – Wikipedia,
Tetrahydropyran – an overview | ScienceDirect Topics

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Synthesis and characterization of monosaccharide derivatives and application of sugar-based prolinamides in asymmetric synthesis

For the first time, the beta-anomer of N-acetylglucosamine derivative methyl 2-acetamido-3,4,6-tri-O-benzyl-2-deoxy-beta-D-glucopyranoside (9b) was synthesized, isolated, and used in the synthesis of sugar-based primary amine 4b. Sugar-based primary amine 5a, an anomeric pair of monosaccharide derivatives 6a and 6b, and precursors to all these compounds were also synthesized, isolated, and well studied by standard spectroscopic methods, including 2D NMR spectroscopy experiments such as 1H-1H COSY and HSQC. Then sugar-based primary amines 4a, 5a, 6a, and 6b were converted into the corresponding prolinamide organocatalysts (i.e., 1a, 2a, 3a, and 3b) in high yields. The catalytic activity of these sugar-based prolinamide organocatalysts was demonstrated in asymmetric aldol reactions in various solvents and at different temperatures. The oraganocatalyst 3a was shown to be an efficient and powerful organocatalyst for the enantioselective aldol reaction of various cyclic or acyclic ketones with aromatic aldehydes in a mild and facile reaction, which gave the corresponding aldol adducts with high levels of diastereoselectivity (up to 99:1) and enantioselectivity (up to >99 %) in almost all cases.

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

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Synthesis of five nona-beta-(1?6)-d-glucosamines with various patterns of N-acetylation corresponding to the fragments of exopolysaccharide of Staphylococcus aureus

A series of five 3-acetamidopropyl beta-glycosides of nona-beta-(1?6)-glucosamines containing two N-acetylglucosamine residues separated by a different number of glucosamine units with free amino groups have been synthesized using a convergent blockwise approach. Oxazoline glycosylation was used to introduce N-acetylglucosamine residues. These nonasaccharides are structurally related to the poly-N-acetylglucosamine (PNAG) extracellular polysaccharide of Staphylococcus aureus and can be used as models for biochemical and immunological studies.

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Tetrahydropyran – Wikipedia,
Tetrahydropyran – an overview | ScienceDirect Topics