Direct separation of carboxylic acid and amine enantiomers by high-performance liquid chromatography on reversed-phase silica gels coated with chiral copper(II) complexes

Ôi, Naobumi; Kitahara, Hajimu; Aoki, Fumiko

doi:10.1016/0021-9673(95)00350-v

Cited by 36 publications

(5 citation statements)

References 5 publications

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“…R-SBC hydrophobically binds to the RP-18 solid support, thus producing a stable, dynamically coated chiral stationary phase. The presence of a sulfur atom in the amino acid side chain of the selector covalently 19 or hydrophobically bound 5,20,21 to the solid support has been already reported. The chiral selector in the coated phase was N,Sdioctyl-D-penicillamine, which binds to the C-18 carbon chains through both the C-8 alkyl substituents.…”

Section: Introductionmentioning

confidence: 92%

Dynamic ligand‐exchange chiral stationary phase from S‐benzyl‐(R)‐cysteine

et al. 2006

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S-benzyl-(R)-cysteine (R-SBC) is a new chiral ligand-exchange stationary phase which has proved to be effective in the analytical separation of some natural and unnatural underivatized amino acids with fair to good separation and resolution factors. The dynamic coating of the RP-18 solid support with S-Benzyl-(R)-cysteine (R-SBC) gives rise to a stable and efficient chiral stationary phase (CSP) that has been successfully employed. The mechanism of chiral recognition is discussed and a molecular modeling study aimed at identifying molecular descriptors responsible for observed different behaviours of analytes upon different albeit closely related selectors is discussed.

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Section: Introductionmentioning

confidence: 92%

Dynamic ligand‐exchange chiral stationary phase from S‐benzyl‐(R)‐cysteine

et al. 2006

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“…The herein discussed ligand-exchange column consists of a copper(II)− N , S -dioctyl- d -penicillamine complex embedded in reversed-phase (C 18 ) silica. , This type of column is based on the pioneering work of Davankov and co-workers. − Chiral discrimination is a result of the formation of diastereomeric complexes between the enantiomeric analytes and the chiral selector with copper(II) as metal ion. d -Penicillamine as a tridentate ligand can interact with Cu 2+ via its N-, O- and/or S-atom, and therefore complex formation is more manifold than with the often used bidentate ligands such as proline.…”

mentioning

confidence: 99%

A Thermodynamic Study of the Temperature-Dependent Elution Order of Cyclic α-Amino Acid Enantiomers on a Copper(II)−d-Penicillamine Chiral Stationary Phase

Schlauch

Frahm

2000

Anal. Chem.

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The reversal of the elution order of cyclic alpha-amino acid enantiomers as a function of the temperature on a copper(II)-N,S-dioctyl-D-penicillamine ligand-exchange column is described. The thermodynamic parameters accounting for the retention and the separation of analytes were determined by means of van't Hoff plots. The influence of different chromatographic conditions on these parameters was investigated, showing little effect of the Cu(II) concentration in the eluent but strong influence of the organic modifier content on the separation. Further, the pH of the mobile phase was found to be a determining factor for the retention of the analytes. Based on these findings, a separation mechanism is postulated comprising the importance of complex formation for primary docking at the stationary phase, while hydrophobic interactions are crucial for chiral discrimination.

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“…The enantiomeric resolution is based on the diastereomeric interaction of the amino functionalities of the solute with the copper(II)-penicillamine complex of the coated reversedphase silica gel chiral stationary phase. 18 Retention times of 23.7 min. and 42.8 min.…”

Section: Resultsmentioning

confidence: 99%

Expeditious synthesis and chromatographic resolution of (+)- and (?)-trans-1-benzylcyclohexan-1,2-diamine hydrochlorides

Bisel¹,

Schlauch²,

Weckert

et al. 2001

Chirality

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The hitherto unknown (-)- and (+)-1-benzylcyclohexan-1,2-diamine hydrochlorides 4a. HCl and 4b. HCl were synthesized by means of diastereoselective alpha-iminoamine rearrangement with subsequent imine reduction and hydrogenolysis. The relative trans-configuration as well as the absolute (1S,2R) and (1R,2S) configurations of 4a and 4b, respectively, were elucidated on the basis of an X-ray analysis of 3b. HCl. The enantiomeric excess (ee) values of the title compounds (>99%) were determined by chiral HPLC on a Chirex (D) Penicillamine column.

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Direct separation of carboxylic acid and amine enantiomers by high-performance liquid chromatography on reversed-phase silica gels coated with chiral copper(II) complexes

Cited by 36 publications

References 5 publications

Dynamic ligand‐exchange chiral stationary phase from S‐benzyl‐(R)‐cysteine

Dynamic ligand‐exchange chiral stationary phase from S‐benzyl‐(R)‐cysteine

A Thermodynamic Study of the Temperature-Dependent Elution Order of Cyclic α-Amino Acid Enantiomers on a Copper(II)−d-Penicillamine Chiral Stationary Phase

Expeditious synthesis and chromatographic resolution of (+)- and (?)-trans-1-benzylcyclohexan-1,2-diamine hydrochlorides

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