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Neo-glycopeptides: the importance of sugar core conformation in oxime-linked glycoprobes for interaction studies

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Abstract

Carbohydrate binding proteins, such as lectins, are crucial in numerous biological recognition processes. While binding may be mediated by a single monosaccharide, several lectins have shown exquisite epimer and linkage recognition indicating that a larger structure is essential for optimal interaction. Several approaches have been described for their detailed study, including lectinosorbent assays, microarrays and surface plasmon resonance (SPR). Most of these approaches ignore that the aglycon-bound monosaccharide is often in a non-natural conformation that affects the occurring binding event. In this paper we demonstrate that oxime-bound glycans, employed in such approaches, occur predominantly in the open form (~70%). Through the use of a secondary amine, the aglycon-bound monosaccharide in the resulting neo-glycopeptide probe is forced into the ring-form. Resulting structures were analyzed by means of nuclear magnetic resonance and differential derivatization experiments. The impact of ring closure was further demonstrated through interaction studies using SPR and various lectins with distinct binding specificities.

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Acknowledgements

This work was supported by the Spanish Ministry of Education and Science (project BIO2005-07592-CO2-02 to D.A.; predoctoral fellowship BES-2006-12879 to C.J.C.) and by Generalitat de Catalunya (SGR 00494). The authors acknowledge Dr. M.A. Molins from the NMR unit of the University of Barcelona for the assistance with the NMR experiments.

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Authors and Affiliations

  1. Department of Experimental and Health Sciences, Pompeu Fabra University, Barcelona Biomedical Research Park, Dr. Aiguader 88, 08003, Barcelona, Spain

    Carmen Jiménez-Castells, Beatriz G. de la Torre, David Andreu & Ricardo Gutiérrez-Gallego

  2. Pharmacology Research Unit, Bio-analysis Group, Neuropsychopharmacology Program, Municipal Institute of Medical Research IMIM-Hospital del Mar, Barcelona, Spain

    Ricardo Gutiérrez-Gallego

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  1. Carmen Jiménez-Castells
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  2. Beatriz G. de la Torre
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  3. David Andreu
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  4. Ricardo Gutiérrez-Gallego
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Correspondence to Ricardo Gutiérrez-Gallego.

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Jiménez-Castells, C., de la Torre, B.G., Andreu, D. et al. Neo-glycopeptides: the importance of sugar core conformation in oxime-linked glycoprobes for interaction studies. Glycoconj J 25, 879–887 (2008). https://doi.org/10.1007/s10719-008-9150-8

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  • DOI: https://doi.org/10.1007/s10719-008-9150-8

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