A rapid, high-yielding microwave-mediated synthetic procedure was developed and\noptimized using a model system of monovalent sugar linkers, with the ultimate goal of using\nthis method for the synthesis of multivalent glycoclusters. The reaction occurs between the\naldehyde/ketone on the sugars and an aminooxy moiety on the linker/trivalent core molecules used\nin this study, yielding acid-stable oxime linkages in the products and was carried out using equimolar\nquantities of reactants under mild aqueous conditions. Because the reaction is chemoselective, sugars\ncan be incorporated without the use of protecting groups and the reactions can be completed in\nas little as 30 min in the microwave. As an added advantage, in the synthesis of the trivalent\nglycoclusters, the fully substituted trivalent molecules were the major products produced in excellent\nyields. These results illustrate the potential of this rapid oxime-forming microwave-mediated reaction\nin the synthesis of larger, more complex glycoconjugates and glycoclusters for use in a wide variety\nof biomedical applications.
Loading....