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Tandem Use of Optical Sensing and Machine Learning for the Determination of Absolute Configuration, Enantiomeric and Diastereomeric Ratios, and Concentration of Chiral Samples
Author(s) -
De los Santos Zeus A.,
MacAvaney Sean,
Russell Katina,
Wolf Christian
Publication year - 2020
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201912904
Subject(s) - diastereomer , chemistry , salicylaldehyde , enantiomer , hypsochromic shift , absolute configuration , analyte , analytical chemistry (journal) , microscale chemistry , enantiomeric excess , chromatography , stereochemistry , schiff base , organic chemistry , enantioselective synthesis , optics , physics , mathematics education , mathematics , fluorescence , catalysis
We have developed an optical method for accurate concentration, er , and dr analysis of amino alcohols based on a simple mix‐and‐measure workflow that is fully adaptable to multiwell plate technology and microscale analysis. The conversion of the four aminoindanol stereoisomers with salicylaldehyde to the corresponding Schiff base allows analysis of the dr based on a change in the UV maximum at 420 nm that is very different for the homo‐ and heterochiral diastereomers and of the concentration of the sample using a hypsochromic shift of another absorption band around 340 nm that is independent of the analyte stereochemistry. Subsequent in situ formation of Cu II assemblies in the absence and presence of base enables quantification of the er values for each diastereomeric pair by CD analysis. Applying a linear programming method and a parameter sweep algorithm, we determined the concentration and relative amounts of each of the four stereoisomers in 20 samples of vastly different stereoisomeric compositions with an averaged absolute percent error of 1.7 %.