Glycoconjugate Journal

, Volume 25, Issue 9, pp 879–887

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

  • Carmen Jiménez-Castells
  • Beatriz G. de la Torre
  • David Andreu
  • Ricardo Gutiérrez-Gallego
Article

DOI: 10.1007/s10719-008-9150-8

Cite this article as:
Jiménez-Castells, C., de la Torre, B.G., Andreu, D. et al. Glycoconj J (2008) 25: 879. doi:10.1007/s10719-008-9150-8

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.

Keywords

Oxime-linked glycopeptidesCarbohydrate-lectin interactionSPRSecondary amine

Copyright information

© Springer Science+Business Media, LLC 2008

Authors and Affiliations

  • Carmen Jiménez-Castells
    • 1
  • Beatriz G. de la Torre
    • 1
  • David Andreu
    • 1
  • Ricardo Gutiérrez-Gallego
    • 1
    • 2
  1. 1.Department of Experimental and Health SciencesPompeu Fabra UniversityBarcelonaSpain
  2. 2.Pharmacology Research Unit, Bio-analysis Group, Neuropsychopharmacology ProgramMunicipal Institute of Medical Research IMIM-Hospital del MarBarcelonaSpain