- Nucleoside triphosphate mimicry: A sugar triazolyl nucleoside as an ATP-competitive inhibitor of B. anthracis pantothenate kinase
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The synthesis of a library of nucleoside triphoshate mimetics is described where the Mg2+ chelated triphosphate sidechain is replaced by an uncharged methylene-triazole linked monosaccharide sidechain. The compounds have been evaluated as inhib
- Rowan, Andrew S.,Nicely, Nathan I.,Cochrane, Nicola,Wlassoff, Wjatschesslaw A.,Claiborne, Al,Hamilton, Chris J.
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- A one-step β-selective glycosylation of N-acetyl glucosamine and recombinant chitooligosaccharides
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N-Acetyl glucosamine and chitooligosaccharides are selectively converted into β-glycosides without protection of the other hydroxyl groups by alkylation of the anomeric alkoxides in N,N-dimethylformamide containing lithium bromide. Addition of the lithium salt notably improves the stereoselectivity of the glycosylation of the monomer and the efficiency of the process with higher oligomers.
- Vauzeilles, Boris,Dausse, Bruno,Palmier, Sara,Beau, Jean-Marie
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- Novel Glycoconjugate of 8-Fluoro Norfloxacin Derivatives as Gentamicin-resistant Staphylococcus aureus Inhibitors: Synthesis and Molecular Modelling Studies
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Antibiotic resistance has been the subject of interest in clinical practice due to high prevalence of antibiotic-resistant pathogenic organisms. In view of the prevalence of lesser resistance in antibiotics belonging to aminoglycoside class of compounds viz. Food and Drug Administration-approved gentamicin for the treatment of Staphylococcus infections, which also has instances of resistance in the clinical isolates of Staphylococcus aureus, a series of novel glycoconjugates of 8-fluoro norfloxacin analogues with high regio-selectivity by employing copper (I)-catalyzed 1, 3-dipolar cycloaddition of 1-O-propargyl monosaccharides has been synthesized and evaluated for the antibacterial activity against gentamicin resistance Staphylococcus aureus. Among these compounds, the compound 10g showed better antibacterial activity (MIC = 3.12 μg/ml) than gentamicin (Escherichia coli (12.5 μg/ml), Staphylococcus aureus (6.25 μg/ml) and Klebsiella pneumonia (6.25 μg/ml), including gentamicin resistant (>50 μg/ml) strain in vitro). The docking studies suggest DNA gyrase of Staphylococcus aureus as a probable target for the antibacterial action of compound 10g.
- Azad, Chandra S.,Bhunia, Shome S.,Krishna, Atul,Shukla, Praveen K.,Saxena, Anil K.
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- Studies toward the synthesis of linear triazole linked pseudo oligosaccharides and the use of ferrocene as analytical probe
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Three different building blocks have been synthesised and used for the synthesis of linear triazole linked pseudo oligosaccharides with copper(I)-catalysed cycloaddition (CuAAC). Ethynylferrocene has been used as analytical probe to improve the UV/Vis pro
- Schmidt, Magnus S.,G?tz, Kathrin H.,Koch, Wolfgang,Grimm, Tanja,Ringwald, Markus
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- Probing replacement of pyrophosphate via click chemistry; synthesis of UDP-sugar analogues as potential glycosyl transferase inhibitors
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A series of potential UDP-sugar mimics were readily synthesised by copper(I) catalysed modified Huisgen cycloaddition of the corresponding α-propargyl glycosides with 5-azido uridine in aqueous solution. None of the compounds accessed displayed significant inhibitory activity at concentrations of up to 4.5 mM in an assay against bovine milk β-1,4-galactosyltransferase.
- Yeoh, Kar Kheng,Butters, Terry D.,Wilkinson, Brendan L.,Fairbanks, Antony J.
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- Synthesis of bivalent glycoclusters containing GlcNAc as hexasaccharide mimetics. Bactericidal activity against Helicobacter pylori
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The Cu(I) catalysed cycloaddition reaction of azides and alkynes has been used to generate a series of divalent GlcNAc clusters with both α and β configurations. These glycoclusters can be considered as potential mimetics of an anti Helicobacter pylori he
- Yan, Dandan,Naughton, Julie,Clyne, Marguerite,Murphy, Paul V.
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- Sulfuric acid immobilized on silica: an excellent catalyst for Fischer type glycosylation
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Fischer glycosylation, a widely used technique for the preparation of simple alkyl or aryl glycosides, has a few drawbacks including the use of strong mineral acids, excess alcohols, high temperature and long reaction times. This manuscript highlights a modification using sulfuric acid immobilized on silica as catalyst for the preparation of glycosides from free sugars such as d-glucose, d-galactose, d-mannose, l-rhamnose, l-fucose, N-acetyl-d-glucosamine and d-maltose with a diverse range of alcohols to afford a series of useful sugar derivatives in good to excellent yields.
- Roy, Bimalendu,Mukhopadhyay, Balaram
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p. 3783 - 3787
(2008/02/06)
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