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Abstract
A rapid, high-yielding microwave-mediated synthetic procedure was developed and optimized using a model system of monovalent sugar linkers, with the ultimate goal of using this method for the synthesis of multivalent glycoclusters. The reaction occurs between the aldehyde/ketone on the sugars and an aminooxy moiety on the linker/trivalent core molecules used in this study, yielding acid-stable oxime linkages in the products and was carried out using equimolar quantities of reactants under mild aqueous conditions. Because the reaction is chemoselective, sugars can be incorporated without the use of protecting groups and the reactions can be completed in as little as 30 min in the microwave. As an added advantage, in the synthesis of the trivalent glycoclusters, the fully substituted trivalent molecules were the major products produced in excellent yields. These results illustrate the potential of this rapid oxime-forming microwave-mediated reaction in the synthesis of larger, more complex glycoconjugates and glycoclusters for use in a wide variety of biomedical applications.
Highlights
Multivalent glycoconjugates such as glycoclusters, glycodendrimers, glyconanoparticles and glycan microarrays have found a wide range of applications in biochemistry and medicine from studying protein-carbohydrate interactions to developing potential therapeutic agents [1,2,3,4]
In this paper we outline the successful combination of chemoselectivity with a microwave-mediated reaction for purposes of synthesizing a series of oxime-linked monovalent sugar-linker molecules and three trivalent glycoclusters
The trivalent glycoclusters synthesized in this study provide proof of concept for the synthesis of higher order glycoclusters efficiently and excellent isolated yields via a chemoselective microwave synthesis
Summary
Multivalent glycoconjugates such as glycoclusters, glycodendrimers, glyconanoparticles and glycan microarrays have found a wide range of applications in biochemistry and medicine from studying protein-carbohydrate interactions to developing potential therapeutic agents [1,2,3,4]. It has long been recognized in nature that proteins and their binding partners are often displayed in a multivalent fashion. It is well known for carbohydrate-containing molecules that their binding interactions with their biological partners are much stronger when present in multiple copies rather than in a 1:1 ratio. We previously showed that we could use amide coupling between the carboxylic acid-containing unprotected sugar, sialic acid and a poly(amidoamine) (PAMAM) dendrimer core to create a fully substituted 2nd generation 16-mer glycodendrimer that showed μM activity against
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