2-Azidoethyl glycosides: glycosides potentially useful for the preparation of neoglycoconjugates

Chernyak, A. Ya.; Sharma, G. V. M.; Kononov, L. O.; Krishna, Palakodety Radha; Levinsky, Anatoly B.; Kochetkov, Nikolay K.; Rao, A. V. Rama

doi:10.1016/0008-6215(92)80029-z

Cited by 104 publications

(64 citation statements)

References 15 publications

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“…Although not strictly required, all reactions were performed under nitrogen atmosphere. Complexes 5 [14], 6 [15], 11 [16], and 12 [17,18] were synthesised according to the literature procedures. For the investigation of photophysical properties, a dilute solution of the protonated complex (1-4) (5 × 10 −5 M) in water with constant ionic strength ( = 0.1 M using NaCl) was titrated against NaOH.…”

Section: Methodsmentioning

confidence: 99%

Synthesis and Characterisation of First Generation Luminescent Lanthanide Complexes Suitable for Being Adapted for Uptake via the Mannose Receptor

Brooks

Borlace

et al. 2013

Journal of Inorganic Chemistry

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With the aim of directing lanthanide complex uptake via the mannose receptor, a first generation of luminescent lanthanide complexes has been developed with an -D-mannose targeting motif. Four complexes were produced to investigate photophysical properties and determine the effect of the coordinated mannose residue on emission intensity. The free hydroxyls of the -Dmannose residue quenched lanthanide phosphorescence due to their close proximity, though they did not bind the lanthanide centre as observed by q-values ≈1.0 for all complexes between pH 3 and 10. Fluorescent emission was found to vary significantly with pH, though phosphorescent emission was relatively insensitive to pH. This lack of pH sensitivity has the potential to provide stable emission for the visualisation of the endosome-lysosome system where acidic pH is often encountered.

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Section: Methodsmentioning

confidence: 99%

Synthesis and Characterisation of First Generation Luminescent Lanthanide Complexes Suitable for Being Adapted for Uptake via the Mannose Receptor

Brooks

Borlace

et al. 2013

Journal of Inorganic Chemistry

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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: 97%

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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“…Considering that the carbohydrate-protein interactions found in nature are multivalent to allow an efficient and specific recognition of such biomolecules, the immobilization of not only monovalent but also of multivalent carbohydrate displays over silica was planned by choosing the alkyne and azido monosaccharides 7 [33] and 8 [34] as well as the trivalent dendrons 12 and 13 which are readily obtainable by clickchemistry from the pentaerythritol derivative 9 [35] as depicted in Scheme 2. O-Alkylation with an excess of 2-chloroethyl ether [36] gave the trialkynyl derivative 10 suitable for click conjugation with 8.…”

Section: Resultsmentioning

confidence: 99%

Synthesis of Glyco‐Silicas by Cu(I)‐Catalyzed “Click‐Chemistry” and their Applications in Affinity Chromatography

et al. 2006

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The covalent immobilization of suitable alkyne/azide carbohydrate derivatives on complementarily functionalizated azide/alkyne silica was performed by click ligation througth the Cu(I)-catalyzed 1,3-dipolar cycloaddition reaction of such compounds. The new glyco-silicas have shown to be efficient and valuable bio-selective affinity chromatographic supports for the purification of lectins as well as for the one-pot fluorescent labeling of those proteins. The synthetic methodology is simple, high yielding and flexible, allowing the preparation of tailored glyco-silicas with potential future applications in the inmobilization of other biomolecules.

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2-Azidoethyl glycosides: glycosides potentially useful for the preparation of neoglycoconjugates

Cited by 104 publications

References 15 publications

Synthesis and Characterisation of First Generation Luminescent Lanthanide Complexes Suitable for Being Adapted for Uptake via the Mannose Receptor

Synthesis and Characterisation of First Generation Luminescent Lanthanide Complexes Suitable for Being Adapted for Uptake via the Mannose Receptor

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

Synthesis of Glyco‐Silicas by Cu(I)‐Catalyzed “Click‐Chemistry” and their Applications in Affinity Chromatography

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