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

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Activity of ecdysone analogs in enhancing N-acetylglucosamine incorporation into the cultured integument of Chilo suppressalis

Ecdysone analogs with various side chains at the 17-position of the steroid structure enhanced the incorporation of N-acetylglucosamine as 20-hydroxyecdysone into the cultured integument prepared from Chilo suppressalis.Their activity in terms of the concentration required to give 50percent of the maximum response varied with the structure.Piperonyl butoxide, an inhibitor of oxidation metabolism, did not enhance the in vitro effect of the compounds.The order of potency was ponasterone A > 20-hydroxyecdysone > cyasterone > inokosterone > makisterone A >> ecdysone. – Keywords: molting hormone; ecdysone; N-acetylglucosamine; cultured integument; structure-activity relationship; Chilo suppressalis

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Tetrahydropyran – Wikipedia,
Tetrahydropyran – an overview | ScienceDirect Topics

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Purification of alpha-L-fucosidase by C-glycosylic affinity chromatography, and the enzymic synthesis of alpha-L-fucosyl disaccharides

An alpha-L-fucosidase from porcine liver was purified using the new C-glycosylic affinity adsorbent, Sepharose-epsilon-aminocaproyl-3-(alpha-L-fucopyranosyl)propylamine.The C-fucosylic linkage was synthesized by a radical reaction of 2,3,4-tri-O-acetyl-alpha-L-fucopyranosyl bromide with acrylonitrile.In transglycosylation reactions with p-nitrophenyl alpha-L-fucopyranoside or alpha-L-fucopyranosyl fluoride as donor and methyl beta-D-galactopyranoside as acceptor, the enzyme mediated the formation of (1->2)- and (1->6)-linked alpha-L-fucosyl derivatives (6.5 and 10.0percent, respectively).

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Tetrahydropyran – Wikipedia,
Tetrahydropyran – an overview | ScienceDirect Topics

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N-Linked Glycosyl Auxiliary-Mediated Native Chemical Ligation on Aspartic Acid: Application towards N-Glycopeptide Synthesis

A practical approach towards N-glycopeptide synthesis using an auxiliary-mediated dual native chemical ligation (NCL) has been developed. The first NCL connects an N-linked glycosyl auxiliary to the thioester side chain of an N-terminal aspartate oligopeptide. This intermediate undergoes a second NCL with a C-terminal thioester oligopeptide. Mild cleavage provides the desired N-glycopeptide.

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Tetrahydropyran – Wikipedia,
Tetrahydropyran – an overview | ScienceDirect Topics

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Synthesis of 2-acetamido-1,2,4-trideoxy-1,4-imino-D-galactitol, a new hexosaminidase inhibitor

2-Acetamido-1,2,4-trideoxy-1,4-imino-D-galactitol was synthesised from 2-acetamido-2-deoxy-D-glucose in 12 steps and was shown to be a modest hexosaminidase inhibitor.

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

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Synthesis and Hydrolytic Stability of N- and O-Methyloxyamine Linkers for the Synthesis of GlycoconjugatesSynthesis and Hydrolytic Stability of N- and O-Methyloxyamine Linkers for the Synthesis of Glycoconjugates

A comparison of the merits of N- and O-methyloxyamines as linkers for carbohydrates is presented for the first time. In particular, optimized synthetic routes for each linker type are given, and the ease of glycan conjugation is described. The hydrolytic stabilities of the respective oxyamine glycoconjugates under a variety of different conditions are reported. This provides insight into the factors that influence hydrolysis rates, and sheds light on the acid-catalysed hydrolysis mechanism.

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Tetrahydropyran – Wikipedia,
Tetrahydropyran – an overview | ScienceDirect Topics

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COMPOSITIONS AND METHODS FOR JOINT HEALTH

The present disclosure provides mixtures of prenylated flavonoids, stilbenes, or both with flavans or curcuminoids or both capable of modulating joint inflammation, joint pain, joint stiffness, cartilage degradation, or improving mobility, range of motion, flexibility, joint physical function, or any combination thereof. Such a mixture of prenylated flavonoids, stilbenes, or both with flavans or curcuminoids or both can optionally be used in combination with other joint management agents, such as non-steroidal anti-inflammatory agents/analgesics, COX/LOX inhibiting agents, glucosamine compounds, neuropathic pain relief agents, or the like.

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

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Synthesis and evaluation of homoazasugars as glycosidase inhibitors

In an effort to develop transition-state mimetics of the glycosidase-catalyzed reaction, five- and six-membered azasugars and their homo-analogs were prepared and tested as inhibitors of glycosidases. Inhibition studies indicate that the fucosyl cationlike, five-membered imine 1 and its reduced form 2 are potent inhibitors of alpha-fucosidase from bovine kidney with respective K(i) values of 160 nM and 2 muM. The five-membered homoaminoazasugar 3 is also a potent inhibitor of the enzyme (K(i) = 1.9 x 10-6M), while the glucose and mannose-like six-membered homoaminoazasugars 4 and 5 are less potent than the corresponding 1-deoxyazasugars as inhibitors of alpha-glucosidase and alpha-mannosidase, respectively. The primary amino group was placed in an attempt to introduce additional electrostatic interactions in the active site. The inhibitory activities are, however, in the high muM range. Synthesis of homoazasugars structurally related to a disaccharide and a nucleoside is also described.

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

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Synthesis and Structure-Activity Relationship Study of Antimicrobial Auranofin against ESKAPE Pathogens

Auranofin, an FDA-approved arthritis drug, has recently been repurposed as a potential antimicrobial agent; it performed well against many Gram-positive bacteria, including multidrug resistant strains. It is, however, inactive toward Gram-negative bacteria, for which we are in dire need of new therapies. In this work, 40 auranofin analogues were synthesized by varying the structures of the thiol and phosphine ligands, and their activities were tested against ESKAPE pathogens. The study identified compounds that exhibited bacterial inhibition (MIC) and killing (MBC) activities up to 65 folds higher than that of auranofin, making them effective against Gram-negative pathogens. Both thiol and the phosphine structures influence the activities of the analogues. The trimethylphosphine and triethylphosphine ligands gave the highest activities against Gram-negative and Gram-positive bacteria, respectively. Our SAR study revealed that the thiol ligand is also very important, the structure of which can modulate the activities of the AuI complexes for both Gram-negative and Gram-positive bacteria. Moreover, these analogues had mammalian cell toxicities either similar to or lower than that of auranofin.

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

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The isoforms of rat natural killer cell receptor NKR-P1 display a distinct binding of complex saccharide ligands

Lectin-like receptors of natural killer cells are critical for the regulation of their effector function. When these receptors are crosslinked with antibodies or multivalent ligands, they transmit either activating or inhibitory signals. Here we describe binding and inhibition experiments with recombinant extracellular ligand-binding domains of the rat NKR-P1A (activating) and NKR-P1B (inhibitory) receptors. We did not observe any difference in the binding of monosaccharide ligands by these receptors, but revealed dramatic differences in the binding of oligosaccharides and glycodendrimers. Our results explain the immunostimulatory effects of the glycodendrimers, which bind exclusively to the activating NKR-P1A isoform.

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