Document Detail


Versatile strategy for the synthesis of biotin-labelled glycans, their immobilization to establish a bioactive surface and interaction studies with a lectin on a biochip.
MedLine Citation:
PMID:  18347977     Owner:  NLM     Status:  MEDLINE    
Abstract/OtherAbstract:
The emerging role of glycans as versatile biochemical signals in diverse aspects of cellular sociology calls for establishment of sensitive methods to monitor carbohydrate recognition by receptors such as lectins. Most of these techniques involve the immobilization of one of the binding partners on a surface, e.g. atomic force microscopy, glycan array and Surface Plasmon Resonance (SPR), hereby simulating cell surface presentation. Here, we report the synthesis of fluorescent glycoconjugates, with a functionalization strategy which avoids the frequently occurring ring opening at the reducing end for further immobilization on a surface or derivatization with biotin. In order to improve the versatility of these derivatized glycans for biological studies, a new approach for the synthesis of biotinylated and fluorescent glycans has also been realized. Finally, to illustrate their usefulness the neoglycoconjugates were immobilized on different surfaces, and the interaction analysis with a model lectin, the toxin from mistletoe, proved them to act as potent ligands, underscoring the merit of the presented synthetic approach.
Authors:
F Javier Muñoz; Angel Rumbero; José V Sinisterra; J Ignacio Santos; Sabine André; Hans-J Gabius; Jesús Jiménez-Barbero; María J Hernáiz
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Publication Detail:
Type:  Journal Article; Research Support, Non-U.S. Gov't     Date:  2008-03-18
Journal Detail:
Title:  Glycoconjugate journal     Volume:  25     ISSN:  0282-0080     ISO Abbreviation:  Glycoconj. J.     Publication Date:  2008 Oct 
Date Detail:
Created Date:  2008-09-23     Completed Date:  2009-03-19     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  8603310     Medline TA:  Glycoconj J     Country:  United States    
Other Details:
Languages:  eng     Pagination:  633-46     Citation Subset:  IM    
Affiliation:
Grupo de Biotransformaciones, Departamento de Química Orgánica y Farmacéutica, Facultad de Farmacia, Universidad Complutense de Madrid (UCM), Madrid, Spain.
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MeSH Terms
Descriptor/Qualifier:
Amination
Biotin / chemistry*
Biotinylation
Carbohydrate Conformation
Fluorescent Dyes
Glycoconjugates / chemical synthesis,  chemistry
Kinetics
Magnetic Resonance Spectroscopy
Mistletoe / chemistry
Models, Molecular
Plant Lectins / chemistry,  metabolism*
Polysaccharides / chemical synthesis*,  chemistry
Protein Array Analysis*
Surface Plasmon Resonance / methods*
Chemical
Reg. No./Substance:
0/Fluorescent Dyes; 0/Glycoconjugates; 0/Plant Lectins; 0/Polysaccharides; 58-85-5/Biotin

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