Determination of Enantiomeric Excess in Amine Derivatives with Molecular Self-Assemblies

We report the first fluorescence‐based assay for the rapid determination of the ee value of amines, amino alcohols, and amino acid esters. The method uses the self‐assembly of 2‐formylphenylboronic acid with a chiral diol and a chiral amine or derivatives (of unknown chirality) to produce two diaste...

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Bibliographic Details
Published in:Angewandte Chemie International Edition 2015-06, Vol.54 (24), p.7130-7133
Main Authors: Shcherbakova, Elena G., Minami, Tsuyoshi, Brega, Valentina, James, Tony D., Anzenbacher Jr, Pavel
Format: Article
Language:English
Subjects:
Amines
Amines - chemistry
Amino Acids - chemistry
Amino Alcohols - chemistry
Benzaldehydes - chemistry
Boronic Acids - chemistry
Chirality
Covalence
Derivatives
Diols
Dynamics
Fluorescence
Fluorescent Dyes - chemistry
Kinetics
Molecular Conformation
Polarization
Self assembly
sensors
Stereoisomerism
Support Vector Machine
supramolecular chemistry
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Summary:We report the first fluorescence‐based assay for the rapid determination of the ee value of amines, amino alcohols, and amino acid esters. The method uses the self‐assembly of 2‐formylphenylboronic acid with a chiral diol and a chiral amine or derivatives (of unknown chirality) to produce two diastereomeric iminoboronates that differ in their fluorescence intensity and polarization. The approach allows for the accurate determination of the ee value of chiral amines with errors of just 1–2 %. We believe that this application of orthogonal dynamic covalent self‐assembly in the determination of the enantioselectivity will lead to the development of high‐throughput procedures for the determination of chirality. The dynamic covalent self‐assembly of chiral amines with chiral fluorescent diols and 2‐formylphenylboronic acid produces fluorescent diastereomeric iminoboronates that differ in their fluorescence intensity and polarization. This fluorescence‐based assay for the rapid determination of the enantiomeric excess of amine derivatives requires only simple laboratory instrumentation and is amenable to high‐throughput screening.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201501736