Synthetic Approaches to Study Multivalent Carbohydrate—Lectin Interactions

Wittmann, Valentin

doi:10.1002/3527603727.ch2g

Cited by 8 publications

(2 citation statements)

References 17 publications

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“…A possible solution to compensate for these weak individual receptor–ligand interactions is the multivalent presentation of sugar epitopes on suitable scaffolds. This principle is not only used in nature but is also a valid strategy for the construction of artificial lectin ligands [ 3 – 13 ]. Prime examples are the recently described ligands for the Shiga-like [ 14 – 15 ] and cholera toxins [ 16 – 17 ] both belonging to the AB 5 family of bacterial toxins.…”

Section: Introductionmentioning

confidence: 99%

High-affinity multivalent wheat germ agglutinin ligands by one-pot click reaction

Beckmann¹,

Möller²,

Wittmann³

2012

Beilstein J. Org. Chem.

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SummaryA series of six mono-, di-, and trivalent N,N’-diacetylchitobiose derivatives was conveniently prepared by employing a one-pot procedure for Cu(II)-catalyzed diazo transfer and Cu(I)-catalyzed azide–alkyne cycloaddition (CuAAC) starting from commercially available amines. These glycoclusters were probed for their binding potencies to the plant lectin wheat germ agglutinin (WGA) from Triticum vulgaris by an enzyme-linked lectin assay (ELLA) employing covalently immobilized N-acetylglucosamine (GlcNAc) as a reference ligand. IC50 values were in the low micromolar/high nanomolar range, depending on the linker between the two disaccharides. Binding enhancements β up to 1000 for the divalent ligands and 2800 for a trivalent WGA ligand, compared to N,N’-diacetylchitobiose as the corresponding monovalent ligand, were observed. Molecular modeling studies, in which the chitobiose moieties were fitted into crystallographically determined binding sites of WGA, correlate the binding enhancements of the multivalent ligands with their ability to bind to the protein in a chelating mode. The best WGA ligand is a trivalent cluster with an IC50 value of 220 nM. Calculated per mol of contained chitobiose, this is the best WGA ligand known so far.

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Section: Introductionmentioning

confidence: 99%

High-affinity multivalent wheat germ agglutinin ligands by one-pot click reaction

Beckmann¹,

Möller²,

Wittmann³

2012

Beilstein J. Org. Chem.

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“…the phenomenon of multivalency [9,10] frequently associated with the recognition of these substrates have boosted the design and synthesis of a wide range of polyglycosylated compounds [11][12][13][14][15][16][17]. The major aim is to clarify the principles [10,18] of the so-called glycoside cluster effect [19] and find new bioactive molecules for diagnostic [20] and therapy [21][22][23] based on the saccharide recognition.…”

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confidence: 99%

Conformationally Mobile Glucosylthioureidocalix[6]- and Calix[8]arenes: Synthesis, Aggregation and Lectin Binding

Sansone

Baldini

Casnati

et al. 2008

Supramolecular Chemistry

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Azides in Carbohydrate Chemistry

Beckmann

Wittmann

2009

Organic Azides

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I )~.THF.HiO.N~ 2) NB, ~ TI-F . EIOH '''' Schcm c 16.7 SyntheSiS of aminoglycoside derivative 11 using azides as protecting groups for amines. First the amino groups of 18 were converted into azides by diazo /r.lnsfer. l1 After chemical remodeling of the aminoglycoside (one amino group was replaced by a hydroxy grotlp), the amines were regenerated by Stiludinger reduction" 474 Organic Azides: Sylllheses and Applicalions 23 BnO~O BnO~ N °9N'O~N' , 0 0 :1 ~ Cl Y 25 Cl PM~ (1.3 equiv), THF, H~, NaOH 46% PMe3 (1.

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Synthetic Approaches to Study Multivalent Carbohydrate—Lectin Interactions

Cited by 8 publications

References 17 publications

High-affinity multivalent wheat germ agglutinin ligands by one-pot click reaction

High-affinity multivalent wheat germ agglutinin ligands by one-pot click reaction

Conformationally Mobile Glucosylthioureidocalix[6]- and Calix[8]arenes: Synthesis, Aggregation and Lectin Binding

Azides in Carbohydrate Chemistry

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