title: Probing the general time scale question of boronic acid binding with sugars in aqueous solution at physiological pH.
abstract: The boronic acid group is widely used in chemosensor design due to its ability to reversibly bind diol-containing compounds. The thermodynamic properties of the boronic acid-diol binding process have been investigated extensively. However, there are few studies of the kinetic properties of such binding processes. In this report, stopped-flow method was used for the first time to study the kinetic properties of the binding between three model arylboronic acids, 4-, 5-, and 8-isoquinolinylboronic acids, and various sugars. With all the boronic acid-diol pairs examined, reactions were complete within seconds. The k(on) values with various sugars follow the order of D-fructose>D-tagatose>D-mannose>D-glucose. This trend tracks the thermodynamic binding affinities for these sugars and demonstrates that the 'on' rate is the key factor determining the binding constant.
authors.affiliation: Department of Chemistry, Center for Diagnostics and Therapeutics, and Center for Biotechnology and Drug Design, Georgia State University, Atlanta, GA 30302-4098, USA.
authors.forename: Nanting
authors.initials: N
authors.lastname: Ni
authors.forename: Sarah
authors.initials: S
authors.lastname: Laughlin
authors.forename: Yingji
authors.initials: Y
authors.lastname: Wang
authors.forename: You
authors.initials: Y
authors.lastname: Feng
authors.forename: Yujun
authors.initials: Y
authors.lastname: Zheng
authors.forename: Binghe
authors.initials: B
authors.lastname: Wang
mesh_terms: D001897:Boronic Acids / Q000737:chemistry*; D005632:Fructose / Q000737:chemistry; D005947:Glucose / Q000737:chemistry; D006601:Hexoses / Q000737:chemistry*; D006863:Hydrogen-Ion Concentration; D007546:Isoquinolines / Q000737:chemistry; D007700:Kinetics; D008358:Mannose / Q000737:chemistry; D013050:Spectrometry, Fluorescence; D013816:Thermodynamics; D014867:Water / Q000737:chemistry*
chemical_list: C555743:8-isoquinolinylboronic acid; D001897:Boronic Acids; D006601:Hexoses; D007546:Isoquinolines; D014867:Water; D005632:Fructose; D005947:Glucose; D008358:Mannose; C030192:tagatose