Meenakshi Dowlut, D. Hall
Mar 15, 2006
Citations
3
Influential Citations
329
Citations
Quality indicators
Journal
Journal of the American Chemical Society
Abstract
This study describes a new class of carbohydrate-binding boronic acids. ortho-Hydroxymethyl phenylboronic acid (boronophthalide) was shown to be superior to the well-established dialkylamino ("Wulff-type") analogues, and it is more soluble in aqueous solvents. The most significant finding in this work is the surprising ability of ortho-hydroxyalkyl arylboronic acids to complex model glycopyranosides under physiologically relevant conditions. These boronic acid units appear to complex hexopyranosides mainly using their 4,6-diol. This behavior is significant because a majority of cell-surface glycoconjugates present free 4,6-diols. Thus, conjugatable forms of these boronic acids could be used in the design of oligomeric receptors and sensors to exploit multivalency effects. Such receptors could dramatically expand the potential of boronic acids toward the selective recognition of cell-surface glycoconjugates.