Guidelines in Implementing Enantioselective Indicator-Displacement Assays for α-Hydroxycarboxylates and Diols
- 1 March 2005
- journal article
- research article
- Published by American Chemical Society (ACS) in Journal of the American Chemical Society
- Vol. 127 (12) , 4260-4269
- https://doi.org/10.1021/ja0435945
Abstract
Enantioselective association events between boronic acid receptors and bifunctional substrates such as α-hydroxycarboxylates and vicinal diols were exploited to develop enantioselective indicator-displacement assays. It was found that the sensitivity of the assay could be tuned by using either colorimetric or fluorescent indicators. Mathematical principles were established for concurrent determination of concentration and enantiomeric excess (ee) of a chiral analyte, which has been a challenge to the high-throughput analysis of chiral samples. Furthermore, experimental protocols were optimized to maximize the chiral resolution of the assay and to improve the accuracy of the ee measurements.Keywords
This publication has 37 references indexed in Scilit:
- Thermodynamic Analysis of Receptors Based on Guanidinium/Boronic Acid Groups for the Complexation of Carboxylates, α‐Hydroxycarboxylates, and Diols: Driving Force for Binding and CooperativityChemistry – A European Journal, 2004
- Kinetic Control over the Thermal Stability of the In-H Bond: Synthesis and Characterization of Amido Indium Hydride ComplexesAngewandte Chemie International Edition in English, 2004
- Activation of All Bonds of a Methyl Group Attached to an Organic FragmentAngewandte Chemie International Edition in English, 2004
- Study of the Mechanism of Electron-Transfer Quenching by Boron−Nitrogen Adducts in Fluorescent SensorsThe Journal of Physical Chemistry B, 2003
- Stable and Highly Water‐Dispersible, Highly Unsaturated Carotenoid Phospholipids—Surface Properties and Aggregate SizeAngewandte Chemie International Edition in English, 2003
- Designing the Selectivity of the Fluorescent Detection of Amino Acids: A Chemosensing Ensemble for HistidineJournal of the American Chemical Society, 2002
- Boronic Acid Receptors for α-Hydroxycarboxylates: High Affinity of Shinkai's Glucose Receptor for TartrateThe Journal of Organic Chemistry, 2002
- β‐Cyclodextrin‐Modified Diphosphanes as Ligands for Supramolecular Rhodium CatalystsAngewandte Chemie International Edition in English, 1997
- Chemoenzymic Synthesis of Chiral Boronates for the Determination of the Absolute Configuration and Enantiomeric Excess of Bacterial and Synthetic cis-DienediolsThe Journal of Organic Chemistry, 1995
- A Reagent for Determining Optical Purities of Diols by Formation of Diastereomeric Arylboronate EstersAngewandte Chemie International Edition in English, 1994