Simultaneous microbatch screening of enantiorecognition on solid chiral selectors using selected mixtures of test-racemates: a case study on cellulose tris(alpha-phenylpropionate) with configurational diversity.
An improved methodology for microbatch screening in the liquid-solid enantioselective adsorption of racemates by solid chiral selector is presented and illustrated by the evaluation of a series of six cellulose tris(alpha-phenylpropionate) presenting a configurational diversity and cellulose tris (4-methylbenzoate). Analyses were performed on 5 mg scale of chiral selector and 150 microL of supernatant containing a mixture of three test-racemates. Fifteen test-racemates were chosen according to their molecular diversity using a hierarchical clustering approach for seven selected three-dimensional molecular properties. The 15 racemates were sorted in five test mixtures composed of three racemates each according to the following constraints: each triplet of test-racemates can be analyzed without peak overlap on a commercially available chiral stationary phase (CSP). The designed five groups of three racemates may be used for the evaluation of other chiral selectors in view of the preparation of CSPs. This methodology improves the throughput of the evaluation and could be automated.
Roussel
C
C
Laboratoire Stéréochimie Dynamique et Chiralité, ENSSPICAM, UMR CNRS 6516, Université, 13397 Marseille Cedex 20, France. roussel@u3pic105.u-3mrs.fr
Bonnet
B
B
De Riggi
I
I
Suteu
C
C
D000327:Adsorption; D001565:Benzoates; D002482:Cellulose / Q000031:analogs & derivatives; D002851:Chromatography, High Pressure Liquid; D007202:Indicators and Reagents; D010666:Phenylpropionates; D012984:Software; D012996:Solutions; D013237:Stereoisomerism
D001565:Benzoates; D007202:Indicators and Reagents; D010666:Phenylpropionates; D012996:Solutions; C432125:cellulose tris(phenylpropionate); D002482:Cellulose; C009504:4-toluic acid