Charged cyclodextrin derivatives as chiral selectors in capillary electrophoresis

Chankvetadze, Bezhan; Endresz, Gabriele; Blaschke, Gottfried

doi:10.1039/cs9962500141

Cited by 138 publications

(82 citation statements)

References 21 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Receptors 1 were synthesized from optically pure (S)-1,1′-bi-2-naphthol via a set of straight-forward steps involving etherification in the presence of a base, tosylation with TsCl, a modified Williamson synthesis with calix [4]arene 15 in the presence of base, and condensation with 4-amino-m-cresol under alkaline conditions in the presence of K 3 [Fe(CN) 6 ]. Proton NMR analyses confirm that both 1a and 1b contained 1,1′-binaphthylas well as the bis(indophenol)-derived calix [4]crown unit.…”

Section: Synthesis and Structurementioning

confidence: 99%

“…5 Furthermore, capillary electrophoresis has recently been developed for a new methodology in which charged cyclodextrin derivatives are utilized as chiral selectors. 6 An alternative approach using molecular sensor having an ability for visual discrimination between the enantiomers of chiral guest species has attracted considerable attention, because a convenient method to monitor the chirality of the molecules would be most welcome in many areas of analytical chemistry, physiology, pharmaceutical industry, and so on. The design of such molecules constitutes a timely and challenging research topic, and has led to the synthesis of several chromogenic host molecules; also, the colorimetry for chiral recognition has been examined.…”

mentioning

confidence: 99%

See 1 more Smart Citation

Naked-Eye Detectable Chiral Recognition Using a Chromogenic Receptor

et al. 1998

View full text Add to dashboard Cite

This article is concerned with our recent achievement in developing synthetic chromogenic receptors for optical active amines and amino acid derivatives. Pre-organized (S)-1,1'-bi-2-naphthyl-and bis(indophenol)-derived calix[4]crown 1a shows naked-eye detectable chiral recognition between those enantiomers. The spectroscopic properties are reported, as well as an estimation of the enantioselectivity using an HPLC equipped with a chiral packing column.

show abstract

Section: Synthesis and Structurementioning

confidence: 99%

mentioning

confidence: 99%

Naked-Eye Detectable Chiral Recognition Using a Chromogenic Receptor

et al. 1998

View full text Add to dashboard Cite

show abstract

“…[1][2][3][4] As indicated by recent reviews, over the years charged CDs have become the most widely used chiral selectors in CE. [4][5][6][7] However, the majority of these chiral separations were performed with randomly derivatized or substituted CDs containing different numbers of derivatized or substituted groups.…”

Section: Introductionmentioning

confidence: 99%

Chiral separation of catechin by capillary electrophoresis using mono‐, di‐, tri‐succinyl‐β‐cyclodextrin as chiral selectors

et al. 2009

View full text Add to dashboard Cite

The chiral separation of (6)-catechin was investigated by capillary electrophoresis using characterized succinyl-b-cyclodextrins (Suc-b-CDs) with one to three degree of substitution values. The effects of nature and concentration of Suc-b-CDs and running buffer pH on the migration time and resolution of (6)-catechin are discussed. All three kinds of Suc-b-CDs show a clear baseline separation of (6)-catechin in capillary electrophoresis. Mono-Suc-b-CD effectively separated (6)-catechin, and additional substituted CDs (di-and tri-Suc-b-CD) were capable of chiral separation at a broad pH range. The optimum running conditions were found to be 100 mM borate buffer (pH 9.8) containing 5 mM mono-Suc-b-CD with no methanol organic modifier.

show abstract

“…1,2 In particular, many applications with charged CD derivatives have been reported in recent years because charged CDs are much superior to neutral CDs for the separation of oppositely charged enantiomers. [3][4][5] However, most commercial CD derivatives consist of a mixture having different degrees of substitution. Each component of the CD has a different binding constant with the enantiomer.…”

mentioning

confidence: 99%

“…3,[8][9][10] Because CDs are weakly UV absorbing, the indirect UV detection method has usually been used. In a previous study 10 , we also separated a quaternary ammonium b-CD (QA-b-CD) by CZE with an indirect UV detection method.…”

mentioning

confidence: 99%

Analysis of Charged Cyclodextrin Derivatives by On-Line Capillary Electrophoresis-Ionspray-Mass Spectrometry

1998

View full text Add to dashboard Cite

On-line capillary electrophoresis-ionspray-mass spectrometry (CE-ISP-MS) was applied to a composition analysis of charged cyclodextrin (CD) derivatives. Quaternary ammonium b-CD (QA-b-CD) and carboxymethylated g-CD (CM-g-CD), which were used as chiral selectors for enantiomer separations by CE, were analyzed. As for QA-b-CD, eight components having different degrees of the quaternary ammonium substitution could be identified based on their mass spectra. The components were detected as either molecular ions or fragment ions. On the other hand, six components of CMg-CD were detected as bivalent molecular ions. Such composition analyses were difficult using CE with only the UV detector. CE-MS was found to be a promising technique for a composition analysis of mixed compounds.

show abstract

Charged cyclodextrin derivatives as chiral selectors in capillary electrophoresis

Cited by 138 publications

References 21 publications

Naked-Eye Detectable Chiral Recognition Using a Chromogenic Receptor

Naked-Eye Detectable Chiral Recognition Using a Chromogenic Receptor

Chiral separation of catechin by capillary electrophoresis using mono‐, di‐, tri‐succinyl‐β‐cyclodextrin as chiral selectors

Analysis of Charged Cyclodextrin Derivatives by On-Line Capillary Electrophoresis-Ionspray-Mass Spectrometry

Contact Info

Product

Resources

About