A detailed examination of boronic acid–diol complexation

Boronic acids bind with compounds containing diol moieties with high affinity through reversible boronate formation. However, the conditions that foster tight binding between the diol and the boronic acid are not well understood. Also, due to the multiple ionic states of both the boronic acid and bo...

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Bibliographic Details
Published in:Tetrahedron 2002-06, Vol.58 (26), p.5291-5300
Main Authors: Springsteen, Greg, Wang, Binghe
Format: Article
Language:English
Subjects:
acid–diol
boronic acid
phenylboronic acid
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Summary:Boronic acids bind with compounds containing diol moieties with high affinity through reversible boronate formation. However, the conditions that foster tight binding between the diol and the boronic acid are not well understood. Also, due to the multiple ionic states of both the boronic acid and boronate ester, the equilibrium constants reported in the literature have not always been strictly defined, and therefore there is a lack of ‘comparability’ between the reported values. To address these issues, we have developed a method for examining boronate ester stability using the fluorescent reporter Alizarin Red S. We have used this system to determine the binding constants of a series of diols, and as a basis from which to derive a number of relationships that correlate the various equilibrium constants in the literature. Graphic
ISSN:0040-4020
1464-5416
DOI:10.1016/S0040-4020(02)00489-1