A concise solid-phase synthesis of inverse poly(amidoamine) dendrons was developed. Upon introduction of AB2-type monomers, each dendron generation was constructed via one reaction. G2 to G5 dendrons were constructed in a peptide synthesizer in 93%, 89%, 82%, and 78% yields, respectively, within 5 days.

Selective glucose binding was identified through five generations of monoboronic acid-functionalized PAMAM dendrimers. The best selectivity obtained when using G3 dendrimers (1b) generated 71.1, 94.9, and 1309 times stronger binding than when using galactose, fructose, and lactose, respectively. Further experiments using dendrimer analogues and glucose derivatives suggested that two nearby monoboronic acids cooperatively bound one glucose.

No abstract

The preparation of boronic acid containing dendrimers is still a difficult task in dendrimer chemistry. In this investigation, an unanticipated hydrolysis product (4) was identified during the preparation of (G:2)-PAMAM-dendri-(4-phenyl boronic acid)14 (3) by acquiring its 1H NMR, 13C NMR, and UV–vis absorption spectra and IR spectra and comparing them with those of 4-hydroxylbenzoic acid (5). Furthermore, an Alizarin Red S staining analysis, ICP-MS, and 11B NMR spectrum indicated the lack of boronic acid in 4. Finally, treatment of 3 with hydrogen peroxide gave a product that was determined to be identical to dendrimer 4. By analyzing the formation of 4 under various conditions, the presence of numerous primary amines in a PAMAM dendrimer did accelerate the hydrolysis of peripheral boronic acid. This investigation revealed an apparent intrinsic problem that needs to be overcome during the preparation of boronic acid containing dendrimers and related boronic acid containing macromolecules.