A kinetic investigation of boronic acid/diol interactions and pattern-based recognition of [alpha]-chiral carboxylates

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Title: A kinetic investigation of boronic acid/diol interactions and pattern-based recognition of [alpha]-chiral carboxylates
Author: Collins, Byron Elliot
Abstract: Amine -functionalized boronic acids have revolutionized the field of carbohydrate sensing in recent years . Capable of rapidly and reversibly forming cyclic boronate esters with of 1 ,2 - and 1 ,3 -diols , polyols , catechols , and α -hydroxycarboxylic acids , boronic acids have found applications spanning from lipid transport to Hydrogen fuel cells . The majority of the work presented in this dissertation will be aimed at gaining a better understanding of the Boron -Nitrogen interactions in ortho -aminomethyl functionalized boronic acids . Chapter 2 will provide an overview of the mechanistic understanding of boronic acid -diol interactions with a special focus on amine -functionalized boronic acids . Chapters 3 – 5 report the progress made by the Anslyn group to develop a more thorough understanding of Boron -Nitrogen interactions and how they affect boronate ester formation . The first introductory chapter will present a the recent advances that have been made in the development of pattern -based sensor systems . Finally , chapter 6 will present the synthesis of a series of bicycloguanidinium hosts , which will be used in a sensing array for chiral carboxylates .
URI: http : / /hdl .handle .net /2152 /ETD -UT -2010 -05 -759
Date: 2010-09-15

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A kinetic investigation of boronic acid/diol interactions and pattern-based recognition of [alpha]-chiral carboxylates. Doctoral dissertation, University of Texas at Austin. Available electronically from http : / /hdl .handle .net /2152 /ETD -UT -2010 -05 -759 .

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