Next Article in Journal
Alcohol and Apoptosis: Friends or Foes?
Next Article in Special Issue
The Hinge Region of Bovine Zona Pellucida Glycoprotein ZP3 Is Involved in the Formation of the Sperm-Binding Active ZP3/ZP4 Complex
Previous Article in Journal
Immune Mechanisms Linking Obesity and Preeclampsia
Previous Article in Special Issue
Engineering and Characterization of a Fluorescent Native-Like HIV-1 Envelope Glycoprotein Trimer
Article Menu

Export Article

Open AccessArticle
Biomolecules 2015, 5(4), 3177-3192; doi:10.3390/biom5043177

Fluorinated Carbohydrates as Lectin Ligands: 19F-Based Direct STD Monitoring for Detection of Anomeric Selectivity

1
Centre de Recherches sur les Macromolécules Végétales, UPR5301, CNRS-Université Grenoble Alpes, BP53, 38041 Grenoble cédex 09, France
2
CIC bioGUNE, Bizkaia Technological Park, Building 800, 48160 Derio, Spain
3
Ikerbasque, Basque Foundation for Science, 48013 Bilbao, Spain
4
Institut für Physiologische Chemie, Tierärztliche Fakultät der Ludwig-Maximilians-Universität, Veterinärstr. 13, 80539 München, Germany
5
Chemical and Physical Biology, Centro de Investigaciones Biológicas, CIB-CSIC, Ramiro de Maeztu 9, 28040 Madrid, Spain
*
Authors to whom correspondence should be addressed.
Academic Editor: Hans Vliegenthart
Received: 9 June 2015 / Revised: 2 November 2015 / Accepted: 4 November 2015 / Published: 13 November 2015
(This article belongs to the Special Issue Challenges in Glycan, Glycoprotein and Proteoglycan Research)
View Full-Text   |   Download PDF [769 KB, uploaded 13 November 2015]   |  

Abstract

The characterization of the binding of reducing carbohydrates present as mixtures of anomers in solution to a sugar recepor (lectin) poses severe difficulties. In this situation, NMR spectroscopy enables the observation of signals for each anomer in the mixture by applying approaches based on ligand observation. Saturation transfer difference (STD) NMR allows fast and efficient screening of compound mixtures for reactivity to a receptor. Owing to the exceptionally favorable properties of 19F in NMR spectroscopy and the often complex 1H spectra of carbohydrates, 19F-containing sugars have the potential to be turned into versatile sensors for recognition. Extending the recently established 1H → 1H STDre19F-NMR technique, we here demonstrate its applicability to measure anomeric selectivity of binding in a model system using the plant lectin concanavalin A (ConA) and 2-deoxy-2-fluoro-d-mannose. Indeed, it is also possible to account for the mutual inhibition between the anomers on binding to the lectin by means of a kinetic model. The monitoring of 19F-NMR signal perturbation disclosed the relative activities of the anomers in solution and thus enabled the calculation of their binding affinity towards ConA. The obtained data show a preference for the α anomer that increases with temperature. This experimental approach can be extended to others systems of biomedical interest by testing human lectins with suitably tailored glycan derivatives. View Full-Text
Keywords: agglutinin; carbohydrates; drug design; glycans; glycoproteins; lectins; sugar receptors agglutinin; carbohydrates; drug design; glycans; glycoproteins; lectins; sugar receptors
Figures

Figure 1

This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

Scifeed alert for new publications

Never miss any articles matching your research from any publisher
  • Get alerts for new papers matching your research
  • Find out the new papers from selected authors
  • Updated daily for 49'000+ journals and 6000+ publishers
  • Define your Scifeed now

SciFeed Share & Cite This Article

MDPI and ACS Style

Ribeiro, J.P.; Diercks, T.; Jiménez-Barbero, J.; André, S.; Gabius, H.-J.; Cañada, F.J. Fluorinated Carbohydrates as Lectin Ligands: 19F-Based Direct STD Monitoring for Detection of Anomeric Selectivity. Biomolecules 2015, 5, 3177-3192.

Show more citation formats Show less citations formats

Related Articles

Article Metrics

Article Access Statistics

1

Comments

[Return to top]
Biomolecules EISSN 2218-273X Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert
Back to Top