- Glycosylation in flow: effect of the flow rate and type of the mixer
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The influence of the flow rate and the mode of mixing of reagent solutions on the result of glycosylation of isopropyl alcohol with glycooxazoline in 1,2-dichloroethane in the presence of (±)-camphor-10-sulfonic acid was studied. No reaction products were observed at low flow rates (?0.043 mL h?1) when using two Comet X-01 micromixers. Under these conditions, the disaggregation of supramers of the reagents is apparently inefficient for the reaction between them to occur. However, when one of the Comet X-01 micromixers was replaced with a T-shaped adapter (at the same flow rate), the expected reaction products, glycoside and glycal, appeared in the reaction mixture. This apparently suggests a higher disaggregation of the supramers reagents under these conditions, which allows the chemical reaction between them to occur.
- Myachin,Orlova,Kononov
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p. 2126 - 2129
(2019/12/23)
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- Synthesis of anti-inflammatory α-and β-linked acetamidopyranosides as inhibitors of toll-like receptor 4 (TLR4)
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Abstract The low-molecular weight isopropyl 2-acetamido-α-glucoside 16 (C34) inhibits toll-like receptor 4 (TLR4) in enterocytes and macrophages in vitro, and reduces systemic inflammation in mouse models of endotoxemia and necrotizing enterocolitis. We used a copper(II)-mediated solvolysis of anomeric oxazolines and an acid-mediated conversion of β-glucosamine and β-galactosamine pentaacetates to generate analogs of 16 at the anomeric carbon and at C-4 of the pyranose ring. These compounds were evaluated for their influence on TLR4-mediated inflammatory signaling in cultured enterocytes and monocytes. Their efficacy was confirmed using a NF-kB-luciferase reporter mouse, thus establishing the first structure-activity relationship (SAR) study in this series and identifying the more efficacious isopropyl 2-acetamido-α-galactoside 17.
- Wipf, Peter,Eyer, Benjamin R.,Yamaguchi, Yukihiro,Zhang, Feng,Neal, Matthew D.,Sodhi, Chhinder P.,Good, Misty,Branca, Maria,Prindle, Thomas,Lu, Peng,Brodsky, Jeffrey L.,Hackam, David J.
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p. 3097 - 3100
(2015/06/02)
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- NOVEL TLR4 INHIBITORS FOR THE TREATMENT OF HUMAN INFECTIOUS AND INFLAMMATORY DISORDERS
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The present invention relates to methods of treating infectious, inflammatory and post-traumatic disorders by administering various compounds newly discovered to have TLR4 inhibitory activity. In addition to methods of treatment, the present invention further provides for pharmaceutical compositions comprising said compounds, together with a suitable pharmaceutical carrier. Because TLR4 is the most upstream receptor in the pro-inflammatory LPS signaling cascade, treatments of the invention, which inhibit or antagonize TLR4 action, may avoid the pitfalls associated with other cytokine inhibitors that act further down the pathway and accordingly play a less specific (and perhaps non-critical) role.
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Paragraph 0080
(2013/11/05)
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- Glycosylated derivatives of substituted hydroxylamine. II. the phase transfer synthesis and the study of the glycosyl transfer reaction of glucosaminides of substituted hydroxylamine
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The interaction of 1-(2-acetamido-3,4,6,-tri-O-acetyl-2-deoxy-β-D- glucopyranosyloxy)benzotriazole with primary and secondary aliphatic and cycloaliphatic alcohols or diisopropylidenegalactose in refluxing methylene chloride under the catalysis of Lewis a
- Kuryanov,Luschtshyk,Chupakhina
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p. 426 - 433
(2013/08/23)
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- Copper(II)-mediated activation of sugar oxazolines: Mild and efficient synthesis of β-glycosides of N-acetylglucosamine
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2-Methyl-(3,4,6-tri- O-acetyl- 1,2-dideoxy-α-D-glucopyrano)-[2,1-d]-2-oxazoline (5) was reacted with glycosyl acceptors bearing primary (6, 8, 10, 20) or secondary hydroxy groups (12, 14, 16, 18) in the presence of anhydrous cupric bromide or cupric chloride at elevated temperature to provide 2-acet-amido-2-deoxy-β-D-glucopyranosides in 36-92% yield. The reaction conditions are milder than those previously described for oxazoline activation employing p-toluenesulfonic acid or ferric chloride. Treatment of the oxazoline with trimethylsilyl azide (22) and CuCl2 leads to 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl azide (23) in 69% yield. Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002).
- Wittmann, Valentin,Lennartz, Dirk
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p. 1363 - 1367
(2007/10/03)
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- The mild cleavage of 2-amino-2-deoxy-D-glucoside methoxycarbonyl derivatives.
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The conversion of methyl carbamate to the corresponding free amine is described for a series of 2-amino-2-deoxy-D-glucosamine derivatives. Cleavage of methoxycarbonyl moiety with MeSiCl(3) and triethylamine in dry THF at 60 degrees C and subsequent aqueou
- Yeung,Adamski-Werner,Bernard,Poulenat,Petillo
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p. 3135 - 3138
(2007/10/03)
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- Use of 2-pyridyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-1-thio-β-D-glucopyranoside as a glycosyl donor and methyl iodide as an activator for the synthesis of 1,2-trans-linked saccharides
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The authors report on the successful use of 2-pyridyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-1-thio-β-D- glucopyranoside as a glycosyl donor and methyl iodide as an activator for the synthesis of 1,2-trans-linked saccharides. This synthesis is significant because the 2-amino-2-deoxyglycopyranosides are important constituents of glycoproteins, glycolipids and glycoside antibiotics. All known for their biological functions like antigen-antibody reactions and in cell communication.
- Mereyala,Gurijala
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p. 277 - 280
(2007/10/02)
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- A NEW SYNTHESIS OF 1,2-TRANS-2-ACETAMIDO-2-DEOXYGLYCOPYRANOSIDES VIA 1,2-TRANS-2-DEOXY-2-IODOGLYCOSYL AZIDES
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Trans-addition of iodoazide to the double bond of 3,4,6-tri-O-acetyl-1,5-anhydro-D-arabino-hex-1-enitol yielded 2-deoxy-2-iodoglycosyl azides, which are percursors of 1,2-trans-2-amino-2-deoxyglycopyranosides when treated by an alcohol in the presence of triphenylphosphine.
- Lafont, Dominique,Guilloux, Pascal,Descotes, Gerard
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- STANNOUS TRIFLATE MEDIATED GLYCOSIDATIONS. A STEREOSELECTIVE SYNTHESIS OF 2-AMINO 2-DEOXY-β-D-GLUCOPYRANOSIDES DIRECTLY WITH THE NATURAL N-ACETYL PROTECTING GROUP.
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Variuos 2-acetamido 2-deoxy β-D-glucopyranosides have been prepared in good yield from the crystalline 2-acetamido 3,4,6-tri-O-acetyl 2-deoxy α-D-glucopyranosyl chloride using stannous triflate as promoter.
- Lubineau, Andre,Gallic, Joelle Le,Malleron, Annie
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p. 5041 - 5044
(2007/10/02)
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- N-Allyloxycarbonyl derivatives of D-glucosamine as promotors of 1,2-trans-glucosylation in Koenigs-Knorr reactions and in Lewis acid catalysed condensations
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The use of suitably blocked D-glucosamine derivatives possessing the N-allyloxyxarbonyl protective group of the amino function represents potential new routes to 1,2-trans-glucosylations.Both 3,4,6-tri-O-acetyl-2-N-allyloxycarbonyl-2-amino-2-deoxy-α-D-glu
- Boullanger, Paul,Banoub, Joseph,Descotes, Gerard
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p. 1343 - 1348
(2007/10/02)
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