Selection of an Optimized Adsorbent for Preparative Chromatographic Enantioseparation by Microscale Screening of a Second-Generation Chiral Stationary Phase Library

Welch, Christopher J.; Bhat, Ganapati A.; Protopopova, Marina

doi:10.1021/cc9900091

“…Chiral HPLC of the supernatant allows the determination of the ratio of enantiomers. Welch et al, (1998aWelch et al, ( ,b,1999 and Lindner (Tobler et al, 2000) have described the method in their respective papers. They both addressed the enantioselectivity issues by measuring the ratio of enantiomers in the supernatant.…”

Section: Microbatch Methodsmentioning

confidence: 99%

“…These chiral selectors prepared at the 5 g scale are then packed into a chromatography column and evaluated with test analytes (Welch et al, 1998a). Much more promising is the description by the same authors of microscale synthesis and screening of chiral stationary phases (Welch et al, 1998b).…”

Section: Introductionmentioning

confidence: 99%

“…These chiral selectors prepared at the 5 g scale are then packed into a chromatography column and evaluated with test analytes (Welch et al, 1998a). Much more promising is the description by the same authors of microscale synthesis and screening of chiral stationary phases (Welch et al, 1998b). In this paper, a dipeptide library of 50 members was prepared using silica-based solid synthesis at the 50 mg scale and these individual supports were evaluated using a microbatch technology with N-(2-naphthylalanine) diethylamide as a test-racemate.…”

Section: Introductionmentioning

confidence: 99%

“…This technology has many advantages for rapid discovery of new chromatographic chiral stationary phases since the synthesis is performed on the milligram scale and evaluation can be fully automated with the minimal solvent consumption. Extrapolation was shown to be possible when the selected chiral selector was further optimised using the same technology and packed in a preparative column (Welch et al, 1999).…”

Section: Introductionmentioning

confidence: 99%

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Simultaneous microbatch screening of enantiorecognition on solid chiral selectors using selected mixtures of test‐racemates: a case study on cellulose tris(α‐phenylpropionate) with configurational diversity

Roussel¹,

Bonnet²,

Riggi³

et al. 2001

Biomedical Chromatography

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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.

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“…In the last few years, we and others have developed microbatch methodologies to evaluate the application field of new chiral selectors or to select commercially available chiral stationary phases (CSPs) (Wolf et al, 1993;Nakano et al, 1998Nakano et al, , 2001Welch et al, 1999Welch et al, , 2001Welch et al, , 2002Roussel et al, 2000Roussel et al, , 2001Bluhm et al, 2000;Tobler et al, 2000;Wang et al, 2000;Xu et al, 2001). The so-called microbatch method for the evaluation of solid chiral selectors as potential CSP involves the enantioselective partition of a racemate between the solid chiral support and an achiral solvent.…”

Section: Introductionmentioning

confidence: 99%

Enantiorecognition on solid chiral selectors using microbatch technology: an example of limitation in case of strong association in the racemate

Roussel¹,

Rafii²,

Río³

et al. 2005

Biomedical Chromatography

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When they were independently tested, the enantiomers of N,N'-bis(salicylidene)-trans-1,2-cyclohexanediamine showed a large difference in adsorption on new chiral selectors using microbatch technology. Surprisingly, when these enantiomers were applied on the same supports as a racemic mixture, no discrimination was observed even though suitable adsorption existed. When a mixture enriched in one enantiomer (scalemic mixture) was applied, the resulting supernatant contained the racemic form and the enantiomer in excess was adsorbed on the support together with a part of racemate. This behavior, which militates in favor of a strong heterochiral dimer formation in the racemate, was revealed using microbatch technology but remained hidden on classical column chromatography on chiral support. Molecular dynamics calculations corroborate this hypothesis, showing a favorite binding mode of the heterochiral dimer, which is stabilized by various inter- and intramolecular interactions. Our findings may be considered as a new limitation of microbatch technology, but they may have some inference in case of chiral amplification using the N,N'-bis(salicylidene)-trans-1,2-cyclohexanediamine enantiomers as chiral ligands.

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Combinatorial Methods in Catalysis and Materials Science

Brümmer¹,

Hall²,

Leclerc³

et al. 2003

Ullmann's Encyclopedia of Industrial Chemistry

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The article contains sections titled: 1. Introduction 2. Enzyme Mimetics and Metal Complexes as Enzyme Mimetics 2.1. Combinatorial Libraries of Catalysts as Enzyme Mimetics 2.2. Combinatorial Synthesis Enzyme Mimetics 2.2.1. Hydrolytically Active Metal Complexes 2.2.2. Evolutionary Solid‐Phase Synthesis of Oxygenase Mimics 2.2.3. Libraries of Organic Acylation Catalysts 3. Combinatorial Catalysis in Asymmetric Synthesis 3.1. Combinatorial Catalyst Libraries in Enantioselective Additions of Dialkylzinc Reagents 3.2. Ligands for the Lewis Acid‐Catalyzed Asymmetric Aza Diels ‐ Alder Reaction 3.3. Divergent Ligand Synthesis for Enantioselective Alkylations 3.4. Chiral Phosphine Ligands for Asymmetric Hydrogenation 3.5. Asymmetric Reactions Catalyzed by Schiff Base‐Type Ligands: the Positional Scanning Approach 3.6. Identification of Novel Catalysts for Asymmetric Epoxidations by the Positional Scanning Approach 4. Multidimensional Combinatorial Screening for the Identification of Novel Catalysts 4.1. Catalyst Discovery and Optimization Using Catalyst Arrays 4.2. Parallel Array Screening for Catalyst Optimization Using Discovery and Focused Ligand Libraries 5. One‐Pot, Multi‐Substrate Screening 6. Combinatorial Approaches to Olefin Polymerization Catalysts 7. Combinatorial Inorganic Catalysis 7.1. Combinatorial Libraries of Homogeneous Polyoxometalate‐Based Catalysts 7.2. Combinatorial Libraries and High‐Throughput Screening of Heterogenous Polyoxometalate Catalysts 8. Combinatorial Heterogeneous Catalysis 8.1. Oxidative Dehydrogenation of Ethane 8.2. Oxidative Dehydrogenation of Propane 8.3. Catalytic Oxidation of CO and Reduction of NO 9. Combinatorial Electrocatalysis 9.1. Electrocatalysts for Fuel Cells 9.2. Combinatorial Electrosynthesis 10. High‐throughput Screening Tools for Catalysis 11. Combinatorial Solid‐State Materials Science 11.1. Materials Library Synthesis 11.1.1. Vapor Deposition Techniques 11.1.2. Alternative Library Synthesis Techniques 11.2. High‐Throughput Screening for Materials 11.2.1. Optical Screening 11.2.2. X‐Ray Characterization 11.3. Applications of Materials 11.3.1. Superconductivity 11.3.2. Ferromagnetic Semiconductors 11.3.3. Magnetoresistant Materials 11.3.4. Dielectric and Ferroelectric Materials 11.3.5. Luminescent Materials 12. Organic Materials and Polymers 12.1. Schiff Bases for Nonlinear Optical (NLO) Materials 12.2. Artificial Receptors for Small Organic Molecules 12.3. New Materials for the Separation of Enantiomers 12.4. Molecular Imprinting 12.5. Polymer Topologies and Functionalization 13. Summary and Outlook

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Selection of an Optimized Adsorbent for Preparative Chromatographic Enantioseparation by Microscale Screening of a Second-Generation Chiral Stationary Phase Library

Cited by 31 publications

References 9 publications

Simultaneous microbatch screening of enantiorecognition on solid chiral selectors using selected mixtures of test‐racemates: a case study on cellulose tris(α‐phenylpropionate) with configurational diversity

Simultaneous microbatch screening of enantiorecognition on solid chiral selectors using selected mixtures of test‐racemates: a case study on cellulose tris(α‐phenylpropionate) with configurational diversity

Enantiorecognition on solid chiral selectors using microbatch technology: an example of limitation in case of strong association in the racemate

Combinatorial Methods in Catalysis and Materials Science

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