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A very simple synthesis of GlcNAc-alpha-pyrophosphoryl-decanol: A substrate for the assay of a bacterial galactosyltransferase

Lipid-linked sugar pyrophosphates, such as GlcNAc-pyrophosphoryl undecaprenol, are important intermediates in the biosynthesis of cell-surface bacterial polysaccharides. It was recently demonstrated that much simpler lipids could substitute for undecaprenol while retaining biological activity, thus making efficient synthetic access to this class of compounds highly desirable. In order to facilitate the synthesis of pure substrates for bacterial glycosyltransferases, we have developed a simple ‘two-pot’ synthesis which we demonstrate here for GlcNAc-alpha-pyrophosphoryl-decanol (4). GlcNAc pyrophosphate, produced by mild periodate oxidation/beta-elimination of commercial UDP-GlcNAc, is alkylated using 1-iododecane to yield the target compound 4 in 39% yield. Compound 4 is shown to be an efficient acceptor for a bacterial galactosyltransferase.

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Tetrahydropyran – Wikipedia,
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Some scientific research about 4-(4-Chlorophenyl)dihydro-2H-pyran-2,6(3H)-dione

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Highly diastereoselective desymmetrisation of cyclic meso-anhydrides and derivatisation for use in natural product synthesis

A new and efficient desymmetrisation of succinic and glutaric cyclic meso-anhydrides is described, providing excellent yields and diastereoselectivities in most cases. Derivatisation of the desymmetrised products is demonstrated by their conversion into mono-protected 1,4-diols. General synthetic utility of the method is established by its application towards a key fragment in the total synthesis of the immunosuppressant antitumour natural product, rapamycin.

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Tetrahydropyran – Wikipedia,
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Discovery of 2-(4-Bromobutoxy)tetrahydro-2H-pyran

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Preparation of para-terphenylylalkanethiols with different chain lengths

Terphenylylalkanethiols with different chain length were synthesized using palladium-catalyzed cross-coupling reactions. While the thiols with two and three methylene groups were obtained via photoaddition of thiopivalic acid to the respective alkenes, the longer terphenylylalkanethiols were synthesized by two consecutive Kumada cross-coupling reactions followed by a Mitsunobu reaction for the introduction of the sulfur functionality. Georg Thieme Verlag Stuttgart.

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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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Phosphate prodrugs derived from N-acetylglucosamine have enhanced chondroprotective activity in explant cultures and represent a new lead in antiosteoarthritis drug discovery

We report the application of the phosphoramidate ProTide approach, developed by us for antiviral nucleosides, to sugar derivatives with potential chondroprotection against osteoarthritis. In particular, N-acetylglucosamine was converted to a series of 06 arylaminoacyl phosphoramidates with ester and amino acid variation. Compounds were prepared by two routes, with or without sugar protection, and were isolated as phosphate diastereoisomers. The compounds were assayed for cellular toxicity and for inhibition of IL-1 induced glycosaminoglycan (GAG) release (i.e., proteoglycan degradation) from bovine articular cartilage in vitro expiant cultures. By comparison to the N-acetyl glucosamine parent, some of the analogues show a significant enhancement in efficacy in the inhibition of inflammatory cytokine-induced proteoglycan degradation.

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Archives for Chemistry Experiments of 14215-68-0

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Structurally diverse disaccharide analogs of antifreeze glycoproteins and their ability to inhibit ice recrystallization

The beta-D-galactosyl-(1,3)-alpha-N-acetyl-D-galactosamine disaccharide is present in antifreeze glycoproteins (AFGPs). Analogs of this disaccharide including the beta-linked (1,3)-, (1,4)-, and (1,6)-galactosyl-N-acetyl galactosamine and the beta-(1,3)-galactosyl-galactoside were synthesized and evaluated for ice recrystallization inhibition (IRI) activity. The results from this study demonstrate that the b-linked-(1,4) disaccharide exhibits more potent IRI activity than the native b-linked-(1,3) disaccharide. The C2 N-acetyl group of the disaccharide does not affect IRI activity but in monosaccharides, the presence of the C2 N-acetyl group decreases IRI activity. The current study will facilitate the design of potent small-molecule ice recrystallization inhibitors.

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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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Synthesis of a potential 10E4 tetrasaccharide antigen involved in scrapie pathogenesis

To test the hypothesis that tetrasaccharide 3 is involved in scrapie pathogenesis, tetrasaccharide derivative 32 functionalized with an amine linker at the reducing end was synthesized. A (2 + 2) glycosylation approach was chosen to furnish the target compound in fully protected form. To investigate its biological role, tetrasaccharide 32 was further functionalized to the corresponding thiol 33 using Traut’s reagent. During the course of the synthesis, the N,N-diacetyl protecting group proved surprisingly labile to radical and acidic conditions.

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Tetrahydropyran – Wikipedia,
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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 Patent£¬once mentioned of 14215-68-0, Application In Synthesis of N-((2S,3R,4R,5R,6R)-2,4,5-Trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-3-yl)acetamide

METHODS TO INHIBIT HISTONE ACETYLTRANSFERASE USING GLYCOSAMINOGLYCANS

The present invention is directed to methods for inhibition of histone acetyltransferases using glycosaminoglycans. The invention is further directed to methods for treating disorders associated with hyperacetylation by administration of glycosaminoglycans to a patient in need thereof. In one preferred embodiment, the glycosaminoglycan is a heparin or heparan sulfate oligosaccharide. Studies show that removal of sulfate residues from the O-positions of either the uronic acid or the glucosamine did not eliminate the inhibitory activity of heparan sulfate. Since a majority of heparan sulfate binding proteins appear to require O-sulfation, molecules without certain O-sulfations can be used to inhibit HATs while not interacting with most known heparin-binding proteins. In addition, specific sequences of heparin/heparan sulfate can be used to specifically inhibit various HATs.

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One-pot three-enzyme synthesis of UDP-GlcNAc derivatives

A Pasteurella multocida N-acetylglucosamine 1-phosphate uridylyltransferase (PmGlmU) was cloned and used efficiently with an N-acetylhexosamine 1-kinase (NahK-ATCC55813) and an inorganic pyrophosphatase (PmPpA) for one-pot three-enzyme synthesis of UDP-GlcNAc derivatives with or without further chemical diversification.

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More research is needed about 31608-22-7

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Partially fluorinated liquid crystal material

The invention provides LC compositions that exhibit V-shaped switching when aligned in an analog device configuration and exhibit bistability when aligned in a bookshelf-type device configuration. The invention more specifically provides LC compositions of formula 1 and particularly chiral nonracemic compounds of formula 1 which exhibit bistable switching as well as V-shaped switching when aligned in appropriate device configurations. The invention also provides methods of using the compounds of the invention in making LC compositions and electooptical devices comprising an aligned layer of the compositions of this invention.

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Practical preparation of lacto-N-biose I, a candidate for the bifidus factor in human milk

A one-pot enzymatic reaction to produce lacto-N-biose I (LNB), which is supposed to represent the bifidus factor in human milk oligosaccharides, was demonstrated. Approximately 500mM of LNB was generated in 10-liter of reaction mixture initially containing 660 mM of sucrose and 600mM of GlcNAc by the concurrent actions of four enzymes, sucrose phosphorylase, UDP-glucose – hexose-1-phospate uridylyltransferase, UDP-glucose 4-epimerase, and lacto-N-biose phosphorylase, in the presence of UDP-Glc and phosphate, indicating a reaction yield of 83%. LNB was isolated from the mixture by crystallization after yeast treatment. Finally, 1.4 kg of LNB of 99.6% purity was recovered after recrystallization.

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Tetrahydropyran – Wikipedia,
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