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 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.
Department of Chemistry, Bowling Green State University, Bowling Green, OH 43403 (USA).
Elena G
EG
Shcherbakova
Department of Chemistry, Bowling Green State University, Bowling Green, OH 43403 (USA).
Tsuyoshi
T
Minami
Department of Chemistry, Bowling Green State University, Bowling Green, OH 43403 (USA).
Valentina
V
Brega
Department of Chemistry, University of Bath, Claverton Down, Bath BA2 7AY (UK).
Tony D
TD
James
Department of Chemistry, Bowling Green State University, Bowling Green, OH 43403 (USA). pavel@bgsu.edu.
Pavel
P
Anzenbacher
D000588:Amines / Q000737:chemistry*; D000596:Amino Acids / Q000737:chemistry; D000605:Amino Alcohols / Q000737:chemistry; D001547:Benzaldehydes / Q000737:chemistry; D001897:Boronic Acids / Q000737:chemistry; D005456:Fluorescent Dyes / Q000737:chemistry; D007700:Kinetics; D008968:Molecular Conformation; D013237:Stereoisomerism; D060388:Support Vector Machine
C532809:2-formylphenylboronic acid; D000588:Amines; D000596:Amino Acids; D000605:Amino Alcohols; D001547:Benzaldehydes; D001897:Boronic Acids; D005456:Fluorescent Dyes
chirality; fluorescence; self-assembly; sensors; supramolecular chemistry