An Enantioselective Fluorescent Sensor for Sugar Acids
- 16 November 2004
- journal article
- research article
- Published by American Chemical Society (ACS) in Journal of the American Chemical Society
- Vol. 126 (49) , 16179-16186
- https://doi.org/10.1021/ja046289s
Abstract
Chiral fluorescent boronic acid 1 was found to be a highly enantioselective, chemoselective, and sensitive sensor for sugar acids, such as tartaric acid. Enantioselectivities (KR/KS) of up to 550:1, chemoselectivity up to 11 000:1, and sensitivities in the micromolar range with sensor 1 were observed. Single-crystal X-ray analysis was used to confirm the structure of the fluorescent species.Keywords
This publication has 26 references indexed in Scilit:
- Chiral Binol–Bisboronic Acid as Fluorescence Sensor for Sugar AcidsAngewandte Chemie International Edition in English, 2004
- Facile Quantification of Enantiomeric Excess and Concentration with Indicator-Displacement Assays: An Example in the Analyses of α-HydroxyacidsJournal of the American Chemical Society, 2004
- Fluorescence of Organic Molecules in Chiral RecognitionChemical Reviews, 2004
- Study of the Mechanism of Electron-Transfer Quenching by Boron−Nitrogen Adducts in Fluorescent SensorsThe Journal of Physical Chemistry B, 2003
- Boronic Acid Receptors for α-Hydroxycarboxylates: High Affinity of Shinkai's Glucose Receptor for TartrateThe Journal of Organic Chemistry, 2002
- Modular fluorescence sensors for saccharidesJournal of the Chemical Society, Perkin Transactions 1, 2002
- Fluorescent sensing of uronic acids based on a cooperative action of boronic acid and metal chelateChemical Communications, 1997
- Novel Saccharide-Photoinduced Electron Transfer Sensors Based on the Interaction of Boronic Acid and AmineJournal of the American Chemical Society, 1995
- A Glucose‐Selective Molecular Fluorescence SensorAngewandte Chemie International Edition in English, 1994
- Chiral recognition of tartaric acid derivatives by a synthetic receptorJournal of the Chemical Society, Chemical Communications, 1991