Click Multivalent Heterogeneous Neoglycoconjugates - Modular Synthesis and Evaluation of Their Binding Affinities

• Published in: European Journal of Organic Chemistry Vol. 2009; no. 15; pp. 2454 - 2473
• Main Authors: Ortega-Muñoz, Mariano, Perez-Balderas, Francisco, Morales-Sanfrutos, Julia, Hernandez-Mateo, Fernando, Isac-García, Joaquín, Santoyo-Gonzalez, Francisco
• Format: Book Review Journal Article
• Language: English
• Published: Weinheim WILEY-VCH Verlag 01.05.2009; WILEY‐VCH Verlag; Wiley; Wiley-VCH
• Subjects: Carbohydrates; Carbohydrates with 4, 5, 6, ... C atoms, dissacharides and oligosaccharides; Carbohydrates. Nucleosides and nucleotides; Chemistry; Chemistry, Organic; Click chemistry; Cycloaddition; Exact sciences and technology; Glycoconjugates; Ligand design; Multivalency; Organic chemistry; Physical Sciences; Preparations and properties; Science & Technology; Carbohydrates; Glycoconjugates; FUNCTIONALIZED DENDRIMERS; LIGATION; PREDICTABLE TUNABILITY; SUPRAMOLECULAR CHEMISTRY; 1,3-DIPOLAR CYCLOADDITION REACTION; Cycloaddition; Multivalency; CHEMICAL BIOLOGY; LECTIN; Ligand design; AZIDE-ALKYNE CYCLOADDITIONS; D-GALACTOPYRANOSIDES; OCTOPUS GLYCOSIDES; Click chemistry; Lectin; Aldose; Ligand; Glycoprotein; Oside; Mannose; Glycoconjugate; Concanavalin A; Binding protein; Binding capacity; Chemical synthesis; Heterogeneous reaction
• ISSN: 1434-193X; 1099-0690
• DOI: 10.1002/ejoc.200801169

The efficient synthesis of structurally diverse, multivalent, heterogeneous neoglycoconjugates by means of a series of different click‐based strategies is described. The methodology is highly efficient and versatile allowing for easy access to a series of mannose (α‐Man)‐containing glycoconjugates differing in their valency, nature of the scaffold, nature of the constitutive sugars and length of the linker. The influence of those structural parameters on the binding affinities of these glycomimics toward Concanavalin A (Con A) was evaluated.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009) Multivalent neoglycoconjugates containing two different sugars were synthesized by a modular strategy based in the CuI‐catalyzed azide‐alkyne cycloaddition reaction and their binding affinities toward Concanavalin A were evaluated.