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Large-scale production of N-acetyllactosamine through bacterial coupling

A large-scale production system of N-acetyllactosamine, a core structure of various oligosaccharides, was established by a whole-cell reaction through the combination of recombinant Escherichia coli strains and Corynebacterium ammoniagenes. Two recombinant E. coli strains over-expressed the UDP-Gal biosynthetic genes and the beta-(1?4)-galactosyltransferase gene of Neisseria gonorrhoeae, respectively. C. ammoniagenes contributed the production of UTP from orotic acid. N-Acetyllactosamine was accumulated at 279 mM (107 g L-1) after a 38 h reaction (2.5 L in volume) starting from orotic acid, d-galactose, and 2-acetamido-2-deoxy-d-glucose. Copyright (C) 1999 Elsevier Science Ltd.

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Tetrahydropyran – Wikipedia,
Tetrahydropyran – an overview | ScienceDirect Topics

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Facile synthesis of pseudo-C-glycosyl p-amino-dl-phenylalanine building blocks via Amadori rearrangement

We studied the synthesis of pseudo-C-glycosyl amino acid via an Amadori rearrangement in aqueous solution using unprotected d-lactose and a tyrosine analogue: the p-amino-dl-phenylalanine. Two steps were necessary. In the first step, the N-glycosylation of d-lactose was carried out in aqueous conditions. The synthesized N-glycosylamine was stabilized in a second step by the formation of Amadori compound, the N-[beta-d-galactosyl-1-4-(1-deoxyfructos-1-yl)]-p-amino-dl-phenylalani ne. Products were purified and characterized by mass spectrometry and by 1H and 13C NMR. The influence of the temperature, the pH, the nature of acid and the concentration of the acid on the synthesis yield was examined in order to determine the optimum conditions of Amadori rearrangement. In the best conditions, 35% of p-amino-dl-phenylalanine was converted into N-[beta-d-galactosyl-1-4-(1-deoxyfructos-1-yl)]-p-amino-dl-phenylalani ne. For the N-glycosylation, a specific base catalysis took place in the media whereas a general acid catalysis was observed for the Amadori rearrangement using weak acids and with a temperature close to 75 C. The Amadori compound from glucose [N-(1-deoxyfructopyranos-1-yl)-p-amino-dl-phenylalanine] was also synthesized and characterized by mass spectrometry and by 1H and 13C NMR.

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Tetrahydropyran – Wikipedia,
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Some scientific research about 2-(3-Bromopropoxy)tetrahydro-2H-pyran

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Selective Heck reaction of electron-rich aryl bromides with cyclic alkenones

A simple and efficient protocol for the Heck reaction of cyclic alkenones with electron-rich aryl bromides has been developed. A ligand combination of X-Phos and tri-tert-butylphosphonium hydrogen tetrafluoroborate in the presence of Pd(PPh3)2Cl2 and Na2CO3 in DMSO was found to be efficient and selective for electron-rich aryl bromides with high substrate scope for cyclic alkenones.

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Tetrahydropyran – Wikipedia,
Tetrahydropyran – an overview | ScienceDirect Topics

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MEDICINAL CARBOHYDRATES FOR TREATMENT OF RESPIRATORY CONDITIONS

no abstract published

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Tetrahydropyran – Wikipedia,
Tetrahydropyran – an overview | ScienceDirect Topics

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One-step synthesis of beta-C-glycosidic ketones in aqueous media: The case of 2-acetamido sugars

The one step synthesis of beta-D-C-glycosidic ketones by condensation of pentane-2,4-dione with unprotected N-acetyl-D-gluco-, manno-, and galactosamine in alkaline aqueous media has been explored. N-Acetyl-D-gluco- and mannosamine gave, in good yield, a mixture of the two gluco and manno C-glycosidic ketones, which were separated by crystallization after acetylation, whereas N-acetyl-D-galactosamine afforded the galacto C-glycosidic ketone which was isolated as its acetylated derivative in 50% yield.

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Tetrahydropyran – Wikipedia,
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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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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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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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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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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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