One-pot synthesis of multivalent arrays of mannose mono- and disaccharides

Hayes, Wayne; Osborn, Helen M. I.; Osborne, Sadie D.; Rastall, Robert A.; Romagnoli, Bárbara

doi:10.1016/j.tet.2003.08.011

Cited by 90 publications

(55 citation statements)

References 28 publications

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“…Treatment of tetra-azides 9 [27] and tetrakis(2-propynyloxymethyl)methane 1 in Cu I catalysed click reaction conditions with prop-2-ynyl a-d-mannopyranoside 6 [26] and 2-azidoethyl-2,3,4,6-tetra-O-acetyl-a-d-mannopyranoside 12 [28,29] respectively provided tetramers 11 and 14 in good yields after deacetylation (NaOMe, MeOH) (Scheme 3).…”

Section: Entrymentioning

confidence: 99%

Mannosylated G(0) Dendrimers with Nanomolar Affinities to Escherichia coli FimH

Wellens²,

et al. 2007

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Pentaerythritol and bis-pentaerythritol scaffolds were used for the preparation of first generation glycodendrimers bearing aryl alpha-D-mannopyranoside residues assembled using single-step Sonogashira and click chemistry. The carbohydrate precursors were built with either para-iodophenyl, propargyl, or 2-azidoethyl aglycones whereas the pentaerythritol moieties were built with terminal azide or propargyl groups, respectively. Cross-linking abilities of this series of glycodendrimers were first evaluated with the lectin from Canavalia ensiformis (Concanavalin A). Surface plasmon resonance measurements showed these two families of mannosylated clusters as the best ligands known to date toward Escherichia coli K12 FimH with subnanomolar affinities. Tetramer 4 had a K(d) of 0.45 nM. These clusters were 1000 times more potent than mannose for their capacity to inhibit the binding of E. coli to erythrocytes in vitro.

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Section: Entrymentioning

confidence: 99%

Mannosylated G(0) Dendrimers with Nanomolar Affinities to Escherichia coli FimH

Wellens²,

et al. 2007

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“…Mannose which is known as the principal constituent of carbohydrates present on host cells surface and to which bind the bacterial surface lectins, means of adhesion expressed by bacteria prior to infection. Starting from this mechanism, anti-adhesion drugs for infectious diseases has been developed based on mannose, its derivatives and oligosaccharides [16][17][18]. Thus the EPS from G. hansenii LMG1524 are potentially of high-added value.…”

Section: Introductionmentioning

confidence: 99%

Optimization of Production and Preliminary Characterization of New Exopolysaccharides from <i>Gluconacetobacter hansenii</i> LMG1524

Valepyn¹,

Berezina²,

Paquot³

2012

AiM

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The influence of different carbon and nitrogen sources, of ethanol concentration, the optimal pH, temperature and medium composition were evaluated on extracellular polysaccharides (EPS) synthesis and bacterial growth of Gluconacetobacter hansenii LMG1524, and preliminary characterization of EPS was investigated. The highest EPS yields were obtained using glycerol and ammonium sulphate as carbon and nitrogen sources, respectively. The increase of ethanol concentration in the medium did not influence the EPS synthesis but reduced the bacterial growth. The optimum temperature and pH for polysaccharides production were respectively 25˚C and 5; whereas for cell growth were respectively 30˚C and 4. The optimal culture medium composition was determined as follows: 10 g/L sucrose, 0.892 g/L (NH 4 ) 2 SO 4 , 0.34 g/L NaNO 3 , 3 mL acetic acid, 1.5 g/L KH 2 PO 4 , 1.5 g/L K 2 HPO 4 and 0.6 g/L MgSO 4 . The polysaccharides produced were of 14 and 10 polymerization degrees (DP) and constituted mainly of glucose, galactose and mannose, in relative percent of 36.36, 33.94 and 22.42, respectively.

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“…The synthesis protocol of the galactose linker was performed in four steps according to literatures, 13,22,23 with some modifications. O-Acetyl protected galactose was subsequently bromopropyl substituted, azido substituted, hydrogenation, acylation and deacetylation (Scheme 1).…”

Section: Synthesis Of a Galactose Linkermentioning

confidence: 99%

Galactose-functionalized Magnetic Iron-oxide Nanoparticles for Enrichment and Detection of Ricin Toxin

Liu¹,

Tang²,

Xiao³

et al. 2011

ANAL. SCI.

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One-pot synthesis of multivalent arrays of mannose mono- and disaccharides

Cited by 90 publications

References 28 publications

Mannosylated G(0) Dendrimers with Nanomolar Affinities to Escherichia coli FimH

Mannosylated G(0) Dendrimers with Nanomolar Affinities to Escherichia coli FimH

Optimization of Production and Preliminary Characterization of New Exopolysaccharides from <i>Gluconacetobacter hansenii</i> LMG1524

Galactose-functionalized Magnetic Iron-oxide Nanoparticles for Enrichment and Detection of Ricin Toxin

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One-pot synthesis of multivalent arrays of mannose mono- and disaccharides

Cited by 90 publications

References 28 publications

Mannosylated G(0) Dendrimers with Nanomolar Affinities to Escherichia coli FimH

Mannosylated G(0) Dendrimers with Nanomolar Affinities to Escherichia coli FimH

Optimization of Production and Preliminary Characterization of New Exopolysaccharides from &lt;i&gt;Gluconacetobacter hansenii&lt;/i&gt; LMG1524

Galactose-functionalized Magnetic Iron-oxide Nanoparticles for Enrichment and Detection of Ricin Toxin

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Optimization of Production and Preliminary Characterization of New Exopolysaccharides from <i>Gluconacetobacter hansenii</i> LMG1524