Glycan tagging to produce bioactive ligands for a surface plasmon resonance study via immobilization on different surfaces

Bioconjug Chem. 2009 Apr;20(4):673-82. doi: 10.1021/bc800350q.

Abstract

Suitable glycan derivatives will find immediate application in the study of their interactions. Here, we present an efficient synthetic strategy to introduce a fluorescent tag functionalized with an amino group into a model disaccharide structure (lactose). This strategy led to the maintenance of bioactivity, checked by the study of the interaction of this bioconjugate with a plant lectin (mistletoe lectin 1) by NMR spectroscopy, computational docking, and surface plasmon resonance (SPR). To demonstrate the versatility of this approach, we immobilized the new glycan derivatives on different surfaces, and a comparative analysis is presented and can be successfully used for biomimetic carbohydrate-protein interaction studies on the SPR biochip.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • 2-Naphthylamine / analogs & derivatives
  • 2-Naphthylamine / chemistry
  • Fluorescent Dyes / chemical synthesis
  • Fluorescent Dyes / chemistry*
  • Fluorescent Dyes / metabolism
  • Lactose / chemistry
  • Ligands
  • Molecular Conformation
  • Plant Lectins / metabolism
  • Polysaccharides / chemical synthesis
  • Polysaccharides / chemistry*
  • Polysaccharides / metabolism
  • Ribosome Inactivating Proteins / metabolism
  • Ribosome Inactivating Proteins, Type 2
  • Spectrometry, Fluorescence
  • Spectrophotometry, Ultraviolet
  • Substrate Specificity
  • Surface Plasmon Resonance / methods*
  • Surface Properties
  • Toxins, Biological / metabolism

Substances

  • Fluorescent Dyes
  • Ligands
  • Plant Lectins
  • Polysaccharides
  • Ribosome Inactivating Proteins, Type 2
  • Toxins, Biological
  • VAA-I protein, Viscum album
  • 1,5-diaminonaphthalene
  • 2-Naphthylamine
  • Ribosome Inactivating Proteins
  • Lactose