3-methoxycarbonyl-5-nitrophenyl boronic acid: high affinity diol recognition at neutral pH

Several boronic acids were screened for their ability to bind to diols. 3-Methoxycarbonyl-5-nitrophenyl boronic acid bound to both a catechol dye as well as fructose with a comparable affinity to that of an ortho-methylamino substituted boronic acid. This work suggests a greater role for appropriately functionalized electron deficient boronic acids in diol and carbohydrate recognition. (C) 2003 Elsevier Ltd. All rights reserved.