Synthesis of glycodendrimers by modification of poly(propylene imine) dendrimers

P.R. Ashton, S.E. Boyd, C.L. Brown, S.A. Nepogodiev, E.W. Meijer, H.W.I. Peerlings, J.F. Stoddart

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Abstract

The use of preformed poly(propylene imine) dendrimers (DAB-dendr-(NH2)x) for the rapid and facile construction of high-mol.-wt. carbohydrate-coated dendrimers (glycodendrimers) is presented. An efficient attachment of spacer-armed derivs. of D-galactose and lactose to the primary amino end groups of DAB-dendr-(NH2)x was achieved by means of amide bond formation, using the N-hydroxysuccinimide coupling procedure. Acetate protecting groups were employed in order to avoid side reactions at the coupling stage. Deacetylation leads to the target glycodendrimers. The reactivity of all the available DAB-dendr-(NH2)x (generations 1-5) was investigated and a series of homologous carbohydrate-coated dendrimers were synthesized. In addn., the attachment of larger saccharide moieties was demonstrated by the condensation of a trisgalactoside cluster with DAB-dendr-(NH2)x carrying both four and eight primary amino groups. The regularity of the glycodendrimers was proven by NMR spectroscopy, and the mol. wts. of the low-generation carbohydrate-coated dendrimers were detd. by mass spectrometry. Modifications of DAB-dendr-(NH2)x with biol. active carbohydrates affords a new and simple approach to high mol. wt. compds. that may be considered as neoglycoconjugates with perfectly sym. structures and that offer much promise as multivalent ligands involved in carbohydrate-protein interactions
Original languageEnglish
Pages (from-to)974-984
JournalChemistry : A European Journal
Volume3
Issue number6
DOIs
Publication statusPublished - 1997

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