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Designed Boronate Ligands for Glucose‐Selective Holographic Sensors
Author(s) -
Yang Xiaoping,
Lee MeiChing,
Sartain Felicity,
Pan Xiaohan,
Lowe Christopher R.
Publication year - 2006
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.200600442
Subject(s) - chemistry , intramolecular force , boronic acid , ligand (biochemistry) , combinatorial chemistry , stereochemistry , biochemistry , receptor
In this study, 2‐acrylamidophenylboronate (2‐APB) was synthesised and its ability to bind with glucose was investigated both in solution and when integrated into a holographic sensor. Multiple forms of 2‐APB, resulting from the neighbouring effect of the amido group with the boronic acid through an intramolecular BO‐coordinated interaction, were shown to exist in solution by using multinuclear NMR spectrometry. It was found that 2‐APB predominantly adopts a zwitterionic tetrahedral form at physiological pH values. The complex formation of 2‐APB with glucose and lactate was investigated in DMSO; 2‐APB favours binding with glucose rather than lactate and generates a five‐membered‐ring complex. Furthermore, a 2‐APB‐based holographic sensor displayed a significant response to glucose with little interference from lactate, and with no dependence on pH in the physiological pH range. These features suggest that the new ligand 2‐APB is a potential candidate for the development of glucose‐selective sensors.