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.

journal_name

Bioorg Med Chem

authors

Ni N,Laughlin S,Wang Y,Feng Y,Zheng Y,Wang B

doi

10.1016/j.bmc.2012.03.014

subject

Has Abstract

pub_date

2012-05-01 00:00:00

pages

2957-61

issue

9

eissn

0968-0896

issn

1464-3391

pii

S0968-0896(12)00193-9

journal_volume

20

pub_type

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