TY - JOUR
T1 - Determination of enantiomeric excess in amine derivatives with molecular self-assemblies
AU - Shcherbakova, Elena G.
AU - Minami, Tsuyoshi
AU - Brega, Valentina
AU - James, Tony D.
AU - Anzenbacher, Pavel
PY - 2015/6/8
Y1 - 2015/6/8
N2 - 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.
AB - 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.
UR - http://www.scopus.com/inward/record.url?scp=84930068836&partnerID=8YFLogxK
UR - http://dx.doi.org/10.1002/anie.201501736
U2 - 10.1002/anie.201501736
DO - 10.1002/anie.201501736
M3 - Article
VL - 54
SP - 7130
EP - 7133
JO - Angewandte Chemie-International Edition
JF - Angewandte Chemie-International Edition
SN - 1433-7851
IS - 24
ER -
