Theoretical considerations concerning the separation of enantiomeric solutes by liquid chromatography

Boehm, Richard E.; Martire, Daniel E.; Armstrong, Daniel W.

doi:10.1021/ac00157a006

Cited by 103 publications

(33 citation statements)

References 40 publications

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“…A few diastereoisomers are well separated on traditional normal and reversed phase columns but most of these isomers are difficult to separate [271]. Cyclobondm phases are chiral stationary phases (CSP) [269,272,273] and they were effectively used in separating many compounds [260,269,273], including dansylsulfonamide, b-naphthamide, and b-naphthyl ester derivatives of amino acids, substituted phenylacetic acids, racemic nicotine, substituted dioxolanes, and barbiturates. It was possible to detect as little as 0.20% of one enantiomer in the presence of 99.8% of the other one [266].…”

Section: Cyclobondm Phasesmentioning

confidence: 99%

Synthesis and applications of adsorbents containing cyclodextrins

Crini¹,

2002

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Synthesis and applications of adsorbents containing cyclodextrinsCyclodextrins (CDs), which possess a hydrophobic cavity, have a remarkable capacity to form inclusion complexes with various molecules through host-guest interactions. It is well known that the usefulness of CDs is due to the combination of the inclusion properties and structural features of these molecules. CDs are used extensively in separation science because CD-complexation phenomena offer a procedure of choice for separation of compounds and extraction processes, and provide a useful and versatile tool for protecting the environment. The present review shows the advantages accruing from the use of adsorbents containing cyclodextrins, in particular in chromatographic separations and in waste water treatment. The main goal of this review is to provide a summary of the information concerning the synthesis of materials containing CDs and to give a general overview of the different possible applications of CDs as sorbents in the field of separation techniques. Recent and continuing interest in these adsorbents is evident from the number of papers that appear each year in the literature.

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Section: Cyclobondm Phasesmentioning

confidence: 99%

Synthesis and applications of adsorbents containing cyclodextrins

Crini¹,

2002

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“…Direct evidence for chiral recognition was derived from the crystal structure of an inclusion complex between fenoprofen and b-cyclodextrin by Hamilton et al 3 Statistical thermodynamic theory for chiral recognition in liquid chromatography (LC) was developed by Boehm et al 4 Retention mechanisms have been studied and thermodynamic constants involved in the transfer of solute from mobile to b-CD bonded stationary phase were also determined by Guillaume et al 5 Armstrong et al 6 have also devised an empirical procedure that uses molecular structure to predict enantioselectivity for selected CSPs based on a library of substitution free energy contributions from various side chains attached to a chiral carbon. Armstrong et al 7 have studied enantioresolution mechanisms in GC with cyclodextrin CSPs.…”

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confidence: 99%

Comparison of cyclodextrin-barbiturate noncovalent complexes using electrospray ionization mass spectrometry and capillary electrophoresis

Srinivasan

Bartlett

2000

Rapid Commun. Mass Spectrom.

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Various noncovalent complexes between native and derivatized cyclodextrins (CDs) and barbiturates were studied using capillary electrophoresis (CE) and electrospray ionization mass spectrometry (ESI-MS). This paper involves the study of four aspects of CD-barbiturate noncovalent inclusion complexes. The first study focused on determining the formation of CD-barbiturate inclusion complexes in ESI-MS. This determination was accomplished by the comparison of migration data from CE with ESI-MS inclusion complex peak abundances, which were found to be complementary. The second study found the possibility of predicting native beta-CD mediated CE elution orders for barbiturates using data from ESI-MS. A third study focused on the formation of barbiturate inclusion complexes with derivatized beta-CD and gamma-CD. As part of this study, the effect of the extent of side chain substitution on native CD complexation behavior was investigated. The results indicated that the number of side chains on the CD does not affect the formation of barbiturate complexes with the hydrophobic CD cavity. Finally, a comparison of the hydroxypropyl-beta-CD-barbiturate and hydroxypropyl-gamma-CD-barbiturate complexes in CE and ESI-MS was made to study the relationship between strength of drug-CD binding and enantioresolution. The results from the above studies indicated that the gas phase and the solution state complexes showed comparable behavior indicating that similar interactions played a role in stabilizing these complexes. While it was possible to use the ESI-MS data to determine drug binding to the CDs, it was not possible to predict whether a separation of the enantiomers of a chiral barbiturate would occur. However, the ESI-MS data could be used to eliminate certain CDs from consideration as chiral selectors.

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“…[1][2][3][4] Despite many efforts, [5][6][7] the study of their chiral recognition mechanisms still remains challenging. 8,9 One of the key issues in understanding how CDs work stereoselectively is the enantiomer recognition pattern.…”

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confidence: 99%