An approach to discriminating 25 commercial chiral stationary phases from structural data sets extracted from a molecular database

Roussel, Christian; Piras, Patrick; Heitmann, I.K.

doi:10.1002/(sici)1099-0801(199709)11:5<311::aid-bmc705>3.0.co;2-6

Cited by 19 publications

(5 citation statements)

References 11 publications

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“…Although the database is constructed as a tool for deciding on separation procedures for particular analytes, it may also be used for broad statistical analyses of chiral recognition. One such analysis 60 was aimed at linking various chemical descriptors of both selector and selectands to separation efficiencies and at clustering separation parameters according to these descriptors. Here we attempt the task of mapping the distribution of separation constants and related free-energy differences for the entire CHIRBASE dataset.…”

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confidence: 99%

Probability rule for chiral recognition

Kafri

Lancet

2004

Chirality

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Molecular Chirality is of central interest in biological studies because enantiomeric compounds, while indistinguishable by most inanimate systems, show profoundly different properties in biochemical environments. Enantioselective separation methods, based on the differential recognition of two optical isomers by a chiral selector, have been amply documented. Also, great effort has been directed towards a theoretical understanding of the fundamental mechanisms underlying the chiral recognition process. Here we report a comprehensive data examination of enantio separation measurements for over 72000 chiral selector-select and pairs from the chiral selection compendium CHIRBASE. The distribution of alpha = k'(D)/k'(L) values was found to follow a power law, equivalent to an exponential decay for chiral differential free energies. This observation is experimentally relevant in terms of the number of different individual or combinatorial selectors that need to be screened in order to observe alpha values higher than a preset minimum. A string model for enantiorecognition (SMED) formalism is proposed to account for this observation on the basis of an extended Ogston three-point interaction model. Partially overlapping molecular interaction domains are analyzed in terms of a string complementarity model for ligand-receptor complementarity. The results suggest that chiral selection statistics may be interpreted in terms of more general concepts related to biomolecular recognition.

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confidence: 99%

Probability rule for chiral recognition

Kafri

Lancet

2004

Chirality

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“…[10] This pioneering work was followed by numerous other examples of SDE via achiral chromatography, [1,[3][4][5] as well as the theoretical modelling of chromatographic behaviour of nonracemic compoundsu nder various conditions of achiral chromatography. [27][28][29][30][31][32][33][34] As predicted by Charles and Gil-Av, SDE via achiralc hromatography turned out to be ar emarkably comprehensivep henomenon observed for virtually all types of chiral compounds containing central, [1][2][3][4][5]35] axial, [36][37][38] or helical [39] chirality.I nt his review article,c elebrating the scientificl egacy of ProfessorG il-Av,w ef ocus on our most recent research relating to the subjecto fh is seminal work in this area, [26,30] devoted to SDE via achiral chromatography of chiral amides,i ncluding somey et unpublished results.T he data presented and discussed in this review are divided to threem ajor groups, including amides derived from chiral amines, aamino acids,a nd b-amino acids.I ne ach group,w ed iscuss the observedS DE magnitude as af unction of ac ompoundss tructure,a nd composition of eluent and stationary phases.P articular emphasis is given to the examples which demonstrate the application of SDE via achiral chromatography as an unconventionalm ethod for enan- tiomeric purifications,a ffording,i nm ost of cases,b etter practicalo utcomest han with traditionalf ractional recrystallization.…”

Section: Introductionmentioning

confidence: 94%

Self‐disproportionation of Enantiomers (SDE) of Chiral Nonracemic Amides via Achiral Chromatography

Wzorek

Sato

Drabowicz

et al. 2016

Israel Journal of Chemistry

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This article is based on a review of literature devoted to the phenomenon of SDE via achiral chromatography since the appearance of the seminal work of Professor Emanuel Gil‐Av. The discussed examples of chromatographic studies are related to amides derived from chiral amines and α‐ and β‐amino acids. We discuss the observed SDE magnitude as a function of a compound's structure, and composition of eluent and stationary phases, providing some mechanistic considerations. Particular emphasis is given to the aspect of SDE via achiral chromatography as an emerging unconventional enantiomeric purification technique.

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“…On the other hand, chemoinformatic techniques have been widely applied to both low-and high-molecular-weight chiral selectors, with the aim of studying their chiral discrimination mechanisms and generating predictive models [92]. The simplest strategy to get information on the chiral recognition models for a given selector involves the interpretation of experimental data obtained with a series of analytes displaying structural analogies [93], without a direct calculation of the ligand/selector interaction forces.…”

Section: X-ray Spectroscopic and Chemoinformatic Investigationsmentioning

confidence: 99%

Human Serum Albumin as Chiral Selector in Enantioselective High-Performance Liquid Chromatography

Bertucci¹,

Tedesco²

2017

CMC

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Enantioselective high-performance liquid chromatography (eHPLC) using chiral stationary phases (CSPs) is surely the most used technique for the determination of the enantiomeric excess (e.e.) of chiral drugs, a fundamental parameter for reliable studies on the relationship between stereochemistry and pharmacological activity. A key aspect of this enantioseparation technique is the efficiency of the chiral selector, which can be optimized to obtain higher selectivity and a wider applicability. Thus, the determination of the mechanisms behind chiral recognition is very important to predict and improve the enantioselectivity of CSPs. The present review deals with the preparation and use of CSPs for eHPLC with human serum albumin (HSA) as chiral selector, with particular emphasis on the modulation of the chromatographic performance. HSA-based CSPs allow a relatively easy prediction of the binding sites involved in the retention of analytes and the possibility to improve the selectivity of enantioresolution by modulating the binding process, using either reversible or covalent modifications of the protein. Significant improvements of the chromatographic parameters, such as reduction of analysis time and increase of enantioselectivity, have been obtained for selected analytes by using competitors for a particular binding site of HSA dissolved in the mobile phase or by selectively modifying the protein structure at single amino acid residues.

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An approach to discriminating 25 commercial chiral stationary phases from structural data sets extracted from a molecular database

Cited by 19 publications

References 11 publications

Probability rule for chiral recognition

Probability rule for chiral recognition

Self‐disproportionation of Enantiomers (SDE) of Chiral Nonracemic Amides via Achiral Chromatography

Human Serum Albumin as Chiral Selector in Enantioselective High-Performance Liquid Chromatography

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