Document Detail

Cyclodextrin-based multivalent glycodisplays: covalent and supramolecular conjugates to assess carbohydrate-protein interactions.
MedLine Citation:
PMID:  23340678     Owner:  NLM     Status:  Publisher    
Covalent attachment of biorecognizable sugar ligands in several copies at precise positions of cyclomaltooligosaccharide (cyclodextrin, CD) macrocycles has proven to be an extremely flexible strategy to build multivalent conjugates. The commercial availability of the native CDs in three different sizes, their axial symmetry and the possibility of position- and face-selective functionalization allow a strict control of the valency and spatial orientation of the recognition motifs (glycotopes) in low, medium, high and hyperbranched glycoclusters, including glycodendrimer-CD hybrids. "Click-type" ligation chemistries, including copper(i)-catalyzed azide-alkyne cycloaddition (CuAAC), thiol-ene coupling or thiourea-forming reactions, have been implemented to warrant full homogeneity of the adducts. The incorporation of different glycotopes to investigate multivalent interactions in heterogeneous environments has also been accomplished. Not surprisingly, multivalent CD conjugates have been, and continue to be, major actors in studies directed at deciphering the structural features ruling carbohydrate recognition events. Nanometric glycoassemblies endowed with the capability of adapting the inter-saccharide distances and orientations in the presence of a receptor partner or capable of mimicking the fluidity of biological membranes have been conceived by multitopic inclusion complex formation, rotaxanation or self-assembling. Applications in the fields of sensors, site-specific drug and gene delivery or protein stabilization attest for the maturity of the field.
Alvaro Martínez; Carmen Ortiz Mellet; José M García Fernández
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Publication Detail:
Type:  JOURNAL ARTICLE     Date:  2013-1-23
Journal Detail:
Title:  Chemical Society reviews     Volume:  -     ISSN:  1460-4744     ISO Abbreviation:  Chem Soc Rev     Publication Date:  2013 Jan 
Date Detail:
Created Date:  2013-1-23     Completed Date:  -     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  0335405     Medline TA:  Chem Soc Rev     Country:  -    
Other Details:
Languages:  ENG     Pagination:  -     Citation Subset:  -    
Departamento de Química Orgánica, Facultad de Química, Universidad de Sevilla, c/ Profesor García González 1, E-41012 Sevilla, Spain.
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