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. 2009;48(10):1775-9.
doi: 10.1002/anie.200804905.

A synthetic lectin for O-linked beta-N-acetylglucosamine

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A synthetic lectin for O-linked beta-N-acetylglucosamine

Yann Ferrand et al. Angew Chem Int Ed Engl. 2009.

Abstract

Changing employment: Receptor 1 binds beta-N-acetylglucosaminyl (beta-GlcNAc) up to 100 times more strongly than it does glucose. This synthetic lectin shows affinities similar to wheat germ agglutinin (WGA), a natural lectin used to bind GlcNAc. Remarkably, 1 is more selective than WGA. It favors especially the glycoside unit in glycopeptide 2, a model of the serine-O-GlcNAc posttranslational protein modification.

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Figures

Figure 1
Figure 1
Receptors for all-equatorial carbohydrates. a) Cartoon depicting the general strategy. b) Monosaccharide receptor 5, showing the labelling system used for NMR analysis. Apolar surfaces are shown as blue, spacers red and water-solubilising groups as green.
Figure 2
Figure 2
1H NMR spectra for addition of GlcNAc 6 to receptor 5 (0.5 mM) in D2O, observing the signals due to aromatic protons in the receptor.
Figure 3
Figure 3
1H NMR structure determination of the complex between 5 and 8. a) A portion of the NOESY spectrum of 5 (1 mM) + 8 (8.7 mM) in H2O/D2O (9:1) showing intermolecular contacts between carbohydrate and receptor. Mixing time = 150 ms. Each cross peak is labelled according to the receptor proton (for key, see Fig. 1b), and coloured according to the carbohydrate proton (for key, see inset). b) Derived structure for the complex. Isophthalamide spacer atoms are coloured according to element (C = black, H = white, O = red, N = blue), and the biphenyl units are highlighted in cyan. Carbohydrate 8 is shown as pink, except the OMe and NHAc units which are highlighted in yellow. Intramolecular and intermolecular nOe contacts are shown as green and red dotted lines respectively. The water-solubilising tricarboxylate groups are omitted.
Figure 4
Figure 4
1H NMR spectra for addition of glycopeptide 13 to 5 (0.25 mM) in D2O, observing the signals due to aromatic protons in the receptor.

Comment in

  • Synthetic lectins.
    Kubik S. Kubik S. Angew Chem Int Ed Engl. 2009;48(10):1722-5. doi: 10.1002/anie.200805497. Angew Chem Int Ed Engl. 2009. PMID: 19115356

References

    1. Zachara NE, Hart GW. Chem Rev. 2002;102:431. - PubMed
    1. Hart GW, Housley MP, Slawson C. Nature. 2007;446:1017. - PubMed
    1. Comer FI, Hart GW. J Biol Chem. 2000;275:29179. - PubMed
    1. Wells L, Vosseller K, Hart GW. Science. 2001;291:2376. - PubMed
    1. Zachara NE, Hart GW. Biochimica Et Biophysica Acta-General Subjects. 2004;1673:13. - PubMed

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