Reciprocal principle of molecular recognition in supramolecular chromatography—highly selective analytical separation of cyclodextrin congeners on a silica-bonded [60]fullerene stationary phase

Bogdanski, Anja; Wistuba, Dorothee; Larsen, Kim Lambertsen; Hartnagel, Uwe; Hirsch, Andreas; Schurig, Volker

doi:10.1039/b9nj00725c

Cited by 19 publications

(17 citation statements)

References 31 publications

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“…The covalent immobilization of fullerenes onto various inorganic and organic LC supports, including silica, has also been described through the use of N ‐hydroxysuccinimide, epoxy groups, and amine groups . For instance, an amine‐containing C 60 fullerene was immobilized onto glycidoxypropyl silica , and brominated fullerenes have been covalently attached to amine‐containing silica . In addition, the coupling of fullerenes to silica has been investigated through use of perfluorophenyl azide, as is illustrated in Fig.…”

Section: Incorporation or Immobilization Of Nanomaterials In Lc Systemsmentioning

confidence: 99%

“…Carbon‐based nanomaterials have been used in only a few reports for affinity‐based separations. One such report examined the reciprocal molecular recognition between cyclodextrins and fullerenes and used this effect to resolve cyclodextrin rings of various sizes by using a C 60 fullerene that was immobilized onto silica and placed into a 250 mm × 4.0 mm id column . This approach was found by Bogdanski et al .…”

Section: Nanomaterials In Affinity Chromatography and Chiral Separationsmentioning

confidence: 99%

“…This approach was found by Bogdanski et al . to be complementary in its behavior to work in which the reverse format was employed with immobilized cyclodextrins to separate C 60 and C 70 fullerenes .…”

Section: Nanomaterials In Affinity Chromatography and Chiral Separationsmentioning

confidence: 99%

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Nanomaterials as stationary phases and supports in liquid chromatography

et al. 2017

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The development of various nanomaterials over the last few decades has led to many applications for these materials in liquid chromatography (LC). This review will look at the types of nanomaterials that have been incorporated into LC systems and the applications that have been explored for such systems. A number of carbon-based nanomaterials and inorganic nanomaterials have been considered for use in LC, ranging from carbon nanotubes, fullerenes and nanodiamonds to metal nanoparticles and nanostructures based on silica, alumina, zirconia and titanium dioxide. Many ways have been described for incorporating these nanomaterials into LC systems. These methods have included covalent immobilization, adsorption, entrapment, and the synthesis or direct development of nanomaterials as part of a chromatographic support. Nanomaterials have been used in many types of LC. These applications have included the reversed-phase, normal-phase, ion-exchange, and affinity modes of LC, as well as related methods such as chiral separations, ion-pair chromatography and hydrophilic interaction liquid chromatography. Both small and large analytes (e.g., dyes, drugs, amino acids, peptides and proteins) have been used to evaluate possible applications for these nanomaterial-based methods. The use of nanomaterials in columns, capillaries and planar chromatography has been considered as part of these efforts. Potential advantages of nanomaterials in these applications have included their good chemical and physical stabilities, the variety of interactions many nanomaterials can have with analytes, and their unique retention properties in some separation formats.

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Section: Incorporation or Immobilization Of Nanomaterials In Lc Systemsmentioning

confidence: 99%

Section: Nanomaterials In Affinity Chromatography and Chiral Separationsmentioning

confidence: 99%

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Nanomaterials as stationary phases and supports in liquid chromatography

et al. 2017

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“…To form a 1 : 1 complex, a host (selector) and a guest (selectand) must possess a complementary stereoelectronic arrangement of binding sites and steric barriers . The important link between supramolecular chemistry and separation science has been demonstrated in 1997, and the term “supramolecular chromatography” has been coined in the system fullerene (as selector) and cyclodextrin congeners CD n (as selectands), because the observed selectivity pattern did not follow the conventional elution order according to molecular weight differences, but was governed by a striking shape‐selectivity for medium ring sizes of cyclodextrin congeners …”

Section: Supramolecular Chromatography and The Reciprocal Principle Omentioning

confidence: 99%

On the Centenary of Emanuel Gil‐Av, Former Professor of the Weizmann Institute of Science and Pioneer of Enantioselective Chromatography

Schurig

2016

Israel Journal of Chemistry

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Emanuel Gil‐Av (Zimkin) was born in 1916 and passed away in 1996. The introduction of chemical selectivity into the chromatographic separation process constitutes his main scientific contribution. This approach culminated in the first enantiomeric separation of racemic amino acids by gas chromatography on an optically active chiral stationary phase in 1966, together with Binyamin Feibush and Rosita Charles‐Sigler. Thus the year 2016 marks an important date to remember and to appreciate the invaluable achievements of Gil‐Av in the realm of chirality carried out at the Weizmann Institute of Science, Israel.

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“…[7,15,17] Small amounts of large-ring CD could be obtained by ion exchange chromatography, [15] and CD8-CD10 could be separated using asilica-bonded [60]fullerene stationary phase. [18] Theseparation of CD9 in asingle step was achieved using anormal phase amino column however with high concentrations of acetonitrile as eluent. [16] In contrast, the C18 RP-HPLC phases were capable of separating the large-ring CD with low concentrations of methanol as eluent.…”

mentioning

confidence: 99%

Large‐Ring Cyclodextrins as Chiral Selectors for Enantiomeric Pharmaceuticals

Sonnendecker

Thurmann²,

Przybylski

et al. 2019

Angew Chem Int Ed

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Large-ring cyclodextrins (CD) are cyclic glucans composed of 9o rm ore a-1,4-linked glucose units.T hey are minor side products of bacterial glucanotransferases (CGTases,E C2.4.1.19) and have previously been available only in very small amounts for studies of their properties in supramolecular complex formation reactions.W ee ngineered aCGTase to synthesizemainly large-ring CD facilitating their preparation in larger amounts.B yr eversed phase chromatography,w eo btained single CD samples composed of 10 to 12 glucose units (CD10, CD11, and CD12) with ap urity of > 90 %. Their identity was confirmed by high resolution mass spectrometry and fragmentation analysis.Wedemonstrated the non-toxicity of CD10-CD12 for human cell lines by ac ell proliferation assaya nd impedimetric monitoring.W et hen showed that CD10 and CD11 are efficient chiral selectors for the capillary electrophoretic separation of the enantiomeric pharmaceuticals fluvastatin, mefloquine,c arvedilol, and primaquine.CDa re a-1,4-linked cyclic glucans with ad egree of polymerization (DP) between 6t o> 100. Branched a-1,6-CD have also been described. [1] In contrast to larger CD,CD6, CD7, and CD8 (a-, b-, g-CD) have been studied extensively and are produced commercially. [2] They form cone-shaped structures with ahydrophobic cavity and an outer hydrophilic area, enabling the reversible binding of hydrophobic mole-Supportinginformation and the ORCID identification number(s) for the author(s) of this article can be found under: https://doi.

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Reciprocal principle of molecular recognition in supramolecular chromatography—highly selective analytical separation of cyclodextrin congeners on a silica-bonded [60]fullerene stationary phase

Cited by 19 publications

References 31 publications

Nanomaterials as stationary phases and supports in liquid chromatography

Nanomaterials as stationary phases and supports in liquid chromatography

On the Centenary of Emanuel Gil‐Av, Former Professor of the Weizmann Institute of Science and Pioneer of Enantioselective Chromatography

Large‐Ring Cyclodextrins as Chiral Selectors for Enantiomeric Pharmaceuticals

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