HPTLC separation of aromatic α-amino acid enantiomers on a new histidine-based stationary phase using ligand exchange

Remelli, Maurizio; Piazza, Rossano; Pulidori, F.

doi:10.1007/bf02276253

Cited by 23 publications

(13 citation statements)

References 31 publications

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“…On plates of this type, commercialized first by Macherey-Nagel under the Name 'chiral plate' and later by Merck (Darmstadt, Germany) under the name 'CHIR' plate, a broad spectrum of chelate-complex forming compounds, such as amino acids, a-methylamino acids, N-alkyl amino acids, dipeptides, a-hydroxy acids, halogenated carboxylic acids and some heterocyclic compounds were resolved [311,312,316]. Remelli et al [317] reported on the use of a histidine-based stationary phase for the separation of amino acids.…”

Section: Ligand Exchangementioning

confidence: 99%

Chiral separation by chromatographic and electromigration techniques. A Review

Gübitz

Schmid

2001

Biopharm & Drug Disp

225

135

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This review gives a survey of different chiral separation principles and their use in high-performance liquid chromatography (HPLC), gas chromatography (GC), supercritical fluid chromatography (SFC), thin-layer chromatography (TLC), capillary electrophoresis (CE) and capillary electrochromatography (CEC) highlighting new developments and innovative techniques. The mechanisms of the different separation principles are briefly discussed and some selected applications are shown.

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Section: Ligand Exchangementioning

confidence: 99%

Chiral separation by chromatographic and electromigration techniques. A Review

Gübitz

Schmid

2001

Biopharm & Drug Disp

225

135

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“…His(τ‐dec) was synthesized as previously described . His(τ‐dec) (1.25 g = 4.23 mmol) was dissolved in a mixture of FA (37% w/v, 0.32 cm 3 , 4.23 mmol) and HCl (37% w/v, 10 cm 3 ); the solution was then stirred for 24 h at room temperature.…”

Section: Methodsmentioning

confidence: 99%

“…In this context, several years ago our research group prepared and studied new CCSPs for the chiral separation of amino acids and dipeptides, for both high‐performance liquid chromatography (HPLC) and HPTLC. The chiral selector used was N τ ‐ n ‐decyl‐L‐histidine (His(τ‐dec)) a derivative of L‐His, selectively alkylated at the pyrrole‐like nitrogen of its imidazole ring . In this molecule, the long alkyl chain acts as an anchor for the RP‐18 silica support, while the His residue can form stationary ternary copper complexes with the enantiomers moving in the mobile phase.…”

Section: Introductionmentioning

confidence: 99%

Chiral Ligand‐Exchange Resolution of Underivatized Amino Acids on a Dynamically Modified Stationary Phase for RP‐HPTLC

2014

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The synthesis of Spi(τ-dec), derived from the selective alkylation of L-spinacine (4,5,6,7-tetrahydro-1H-imidazo[4,5-c]pyridine-6-carboxylic acid) at the τ-nitrogen of its heteroaromatic ring, with a linear hydrocarbon chain of 10 carbon atoms, is described here for the first time. Spi(τ-dec) was successfully employed in the past to prepare home-made chiral columns for chiral ligand-exchange high-performance liquid chromatography. In the present article a new method is described, using Spi(τ-dec) as a chiral selector in high-performance thin-layer chromatography (HPTLC): commercial hydrophobic plates were first coated with Spi(τ-dec) and then treated with copper sulfate. The performance of this new chiral stationary phase was tested against racemic mixtures of aromatic amino acids, after appropriate optimization of both the conditions of preparation of the plates and the mobile phase composition. The enantioselectivity values obtained for the studied compounds were higher than those reported in the literature for similar systems. The method employed here for the preparation of chiral HPTLC plates proved practical, efficient, and inexpensive.

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“…We have previously reported the synthesis of N~-decyl-L-histidine, His(T-dec) [11,18,19]. This chiral selector can be strongly adsorbed by the hydrophobic stationary phases used for reversed-phase chromatography, fully preserving the complexing properties of His [20].…”

Section: Introductionmentioning

confidence: 99%

“…This chiral selector can be strongly adsorbed by the hydrophobic stationary phases used for reversed-phase chromatography, fully preserving the complexing properties of His [20]. The chiral modification of RP HPTLC plates [18] and RP HPLC columns [11,19] with His(T-dec), by means of a dynamic coating technique, showed that this chiral selector enables good resolution of racemic mixtures of underivatized amino acid enantiomers.…”

Section: Introductionmentioning

confidence: 99%