title: Synthesis and solvodynamic diameter measurements of closely related mannodendrimers for the study of multivalent carbohydrate-protein interactions.
abstract: This paper describes the synthesis of three closely related families of mannopyranoside-containing dendrimers for the purpose of studying subtle structural parameters involved in the measurements of multivalent carbohydrate-protein binding interactions. Toward this goal, two trimers 5 and 9, three 9-mers 12, 17, 21, and one 27-mer 23, varying by the number of atoms separating the anomeric and the core carbons, were synthesized using azide-alkyne cycloaddition (CuAAc). Compound 23 was prepared by an efficient convergent strategy. The sugar precursors consisted of either a 2-azidoethyl (3) or a prop-2-ynyl α-D-mannopyranoside (7) derivative. The solvodynamic diameters of 9-mer 12, 17, and 21 were determined by pulsed-field-gradient-stimulated echo (PFG-STE) NMR experiments and were found to be 3.0, 2.5, and 3.4 nm, respectively.
authors.affiliation: Pharmaqam, Department of Chemistry, Université du Québec à Montréal, P. O. Box 8888, Succ. Centre-ville, Montréal, Québec, Canada H3C 3P8.
authors.forename: Yoann M
authors.initials: YM
authors.lastname: Chabre
authors.affiliation: Pharmaqam, Department of Chemistry, Université du Québec à Montréal, P. O. Box 8888, Succ. Centre-ville, Montréal, Québec, Canada H3C 3P8.
authors.forename: Alex
authors.initials: A
authors.lastname: Papadopoulos
authors.affiliation: Pharmaqam, Department of Chemistry, Université du Québec à Montréal, P. O. Box 8888, Succ. Centre-ville, Montréal, Québec, Canada H3C 3P8.
authors.forename: Alexandre A
authors.initials: AA
authors.lastname: Arnold
authors.affiliation: Pharmaqam, Department of Chemistry, Université du Québec à Montréal, P. O. Box 8888, Succ. Centre-ville, Montréal, Québec, Canada H3C 3P8.
authors.forename: René
authors.initials: R
authors.lastname: Roy
keywords: carbohydrates; click chemistry; dendrimers; glycodendrimers; lectins; multivalent glycosystems