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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 ?-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.

SUBMITTER: Chabre YM

PROVIDER: S-EPMC4144466 | biostudies-literature | 2014

REPOSITORIES: biostudies-literature

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Synthesis and solvodynamic diameter measurements of closely related mannodendrimers for the study of multivalent carbohydrate-protein interactions.

Chabre Yoann M YM Papadopoulos Alex A Arnold Alexandre A AA Roy René R

Beilstein journal of organic chemistry 20140704

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 ...[more]

PMID: 25165490

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