Enantiomeric separation of dansyl- and dabsylamino acids by ligand-exchange chromatography with (S)- and (R)-phenylalaninamide-modified silica gel

Galli, Beatrice; Gasparrini, Francesco; Misiti, D.; Villani, Claudio; Corradini, Roberto; Dossena, Arnaldo; Marchelli, Rosangela

doi:10.1016/0021-9673(94)80371-4

Cited by 31 publications

(8 citation statements)

References 29 publications

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“…Ligand exchange (LE) chromatography, introduced by Davankov and Rogozhin [1] was shown to be a powerful liquid chromatography (LC) tool with high enantioselectivity for the chiral resolution of chelate complex-forming compounds like amino acids, hydroxy acids, and peptides [2]. LE has been used for chiral separations in several techniques, such as liquid chromatography (LC) [3], capillary electrophoresis (CE) [4±6], and micellar electrokinetic chromatography (MEKC) [7±11]. Capillary electrochromatography (CEC), a separation technique integrating some features of both highperformance liquid chromatography (HPLC) and CE, has received great interest during the 1990s, despite having origins in the 1970s.…”

Section: Introductionmentioning

confidence: 99%

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ChemicallyL-prolinamide-modified monolithic silica column for enantiomeric separation of dansyl amino acids and hydroxy acids by capillary electrochromatography and μ-high performance liquid chromatography

2001

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A silica-based chiral monolithic column prepared by sol-gel process and chemical modification of chiral selector was used for enantioseparation of dansyl amino acids and hydroxy acids by capillary electrochromatography (CEC) and mu-high-performance liquid chromatography (mu-HPLC). L-Prolinamide was modified as a chiral selector. The chiral stationary phase (CSP), the chiral complex of Cu(II) with L-prolinamide, provides an anodic electroosmotic flow (EOF) in CEC. The EOF was found to be dependent on applied electric field strength, the pH, and the composition of mobile phases. Scanning electron micrograph showed that monolithic columns have the morphology of continuous skeleton and large through-pore. D-Enantiomers migrated before L-enantiomers except for dansyl-(Dns)-DL-Ser. The separation efficiencies of up to 17600 (D) and 13,200 plates m(-1) (L) were achieved for the separation of DL-indole-3-lactic acid.

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Section: Introductionmentioning

confidence: 99%

“…Galli et al [3] reported that the enantioseparation of dansyl and dabsyl amino acids by conventional LC using (S) or (R)-phenylalaninamidemodified silica gel as CSP. Our recent work reported on a chemically L-pehnylalaninamide-modified monolithic silica column for enantioseparation of dansyl amino acids by LE-CEC [30].…”

Section: Introductionmentioning

confidence: 99%

ChemicallyL-prolinamide-modified monolithic silica column for enantiomeric separation of dansyl amino acids and hydroxy acids by capillary electrochromatography and μ-high performance liquid chromatography

2001

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“…[54][55][56] In 2001, Chen et al 36 prepared a silica-based monolith via polycondensation of TMOS using a sol-gel process. [54][55][56] In 2001, Chen et al 36 prepared a silica-based monolith via polycondensation of TMOS using a sol-gel process.…”

Section: Ligand-exchange Typementioning

confidence: 99%

“…Ligand-exchange (LE) principles have been extensively utilised in chiral liquid chromatography. [54][55][56] In 2001, Chen et al 36 prepared a silica-based monolith via polycondensation of TMOS using a sol-gel process. The native silica monolith was modified with (3-glycidoxypropyl)trimethoxysilane as spacer then chiral selectors were attached: L -phenylalaninamide, L -alaninamide and L -prolinamide.…”

Section: Ligand-exchange Typementioning

confidence: 99%

An Insight to Chiral Monolith for Enantioselective Nano and Micro HPLC: Preparation and Applications

Healey

Ghanem

2013

Chirality

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This review gives an overview of chiral separation principles and their application in enantioselective nano/micro high performance liquid chromatography (n/μ-HPLC) using chiral monolith. In particular, developments in silica and polymer chiral monolithic stationary phases are presented. The preparation and applications of chiral monoliths, the basic chiral separation principles and the mechanisms are discussed.

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“…The (S)-phenylalaninamide (PheA) molecule was first considered [37] as a potential new chiral selector on account of the good results previously reported in the reversedphase separation of dansyl-amino acids, where it was used as mobile phase chiral additive, as copper(II) complex [38]. In fact, the (S)-PheA Cu(II) complex seemed to be a well established case of classical ligand exchange, with total displacement of a bidentate ligand and substitution with a bidentate analyte.…”

Section: Introductionmentioning

confidence: 99%

Twenty years of research on silica‐based chiral stationary phases

Cancelliere

D’Acquarica

Gasparrini

et al. 2006

J of Separation Science

Self Cite

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This review provides an overview of twenty years of pioneering work (from 1985 to 2005) of our research group in the preparation and application of enantioselective packing materials for HPLC. After a brief introduction to the rational design of a new chiral stationary phase, a detailed presentation in chronological order of appearance in the literature is given of the currently developed repertoire of chiral stationary phases and their typical applications. Emphasis is placed on the different synthetic strategies exploited to obtain highly efficient, stable, and versatile chiral stationary phases.

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Enantiomeric separation of dansyl- and dabsylamino acids by ligand-exchange chromatography with (S)- and (R)-phenylalaninamide-modified silica gel

Cited by 31 publications

References 29 publications

ChemicallyL-prolinamide-modified monolithic silica column for enantiomeric separation of dansyl amino acids and hydroxy acids by capillary electrochromatography and μ-high performance liquid chromatography

ChemicallyL-prolinamide-modified monolithic silica column for enantiomeric separation of dansyl amino acids and hydroxy acids by capillary electrochromatography and μ-high performance liquid chromatography

An Insight to Chiral Monolith for Enantioselective Nano and Micro HPLC: Preparation and Applications

Twenty years of research on silica‐based chiral stationary phases

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