Effects of Temperature and Mobile Phase Condition on Chiral Recognition of Poly(l-phenylalanine) Chiral Stationary Phase

Ohyama, Kaname; Oyamada, Kana; Kishikawa, Naoya; Wada, Mitsuhiro; Ohba, Yoshihito; Nakashima, Kenichiro; Kuroda, Naotaka

doi:10.1007/s10337-011-2092-5

Cited by 4 publications

(3 citation statements)

References 24 publications

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“…With the addition of L-leucine, L-proline, L-phe, or N,N-dimethyl-L-phenylalanine, many enantiomers and derivatized amino acids, such as tryptophan, phenylalanine, warfarin, and valine, have been successfully resolutioned [15][16][17][18]. Considering that DMMD was an analogue of amine acid, the diastereomeric mixed-ligand complexes containing amino acide, bivalence copper, and DMMD could be formed by their carboxylic group and neighboring amino group, which resulted in the cis-and trans-configurations.…”

Section: Resultsmentioning

confidence: 99%

Chiral ligand-exchange high-performance liquid chromatography with copper (II)-L-phenylalanine complexes for separation of 3,4-dimethoxy-α-methylphenylalanine racemes

Jia

Xue

et al. 2014

Anal Bioanal Chem

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L-3, 4-dimethoxy-α-methylphenylalanine (L-DMMD) is an important intermediate for the synthesis of 3-hydroxy-α-methyl-L-tyrosine (L-methyldopa). This paper describes an efficient, accurate, and low-priced method of high-performance liquid chromatography (HPLC) using chiral mobile phase and conventional C18 column to separate L-DMMD from its enantiomers. The effects of ligands, copper salts, organic modifiers, pHs of mobile phase, and temperatures on the retention factors (k') and selectivity (α) were evaluated to achieve optimal separation performance. Then, thermal analysis of the optimal separation conditions was investigated as well. It was confirmed that the optimal mobile phase was composed of 20 % (v/v) methanol, 8 mM L-phenylalanine (L-Phe), and 4 mM cupric sulfate in water of pH 3.2, and the column temperature was set at 20 °C. Baseline separation of two enantiomers could be obtained through the conventional C18 column with a resolution (R) of 3.18 in less than 18 min. Thermodynamic data (∆∆H and ∆∆S) obtained by Van't Hoff plots revealed the chiral separation was an enthalpy-controlled process. To the best of our knowledge, this is the first report regarding the enantioseparation of DMMD by chiral ligand-exchange HPLC.

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Section: Resultsmentioning

confidence: 99%

Chiral ligand-exchange high-performance liquid chromatography with copper (II)-L-phenylalanine complexes for separation of 3,4-dimethoxy-α-methylphenylalanine racemes

Jia

Xue

et al. 2014

Anal Bioanal Chem

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“…Also, Chen used poly(N-benzyl-L-glutamine)-coated silica for the chiral separation of hydantoins [35]. We developed a novel CSP with phenylalanine (Phe) peptide as chiral selector [36][37][38]. The CSP was prepared on APS by solid-phase synthesis with tert-butoxycarbonyl (Boc) amino acids.…”

Section: Preparation and Characterization Of Poly(l-phenylalanine) Chmentioning

confidence: 99%

Development and Pharmaceutical Applications of Functional Stationary Phases for Capillary Electrochromatography and Chiral Separation

Ohyama

2014

Chromatography

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We synthesized 3-(4-sulfo-1,8-naphthalimido)propyl-modified silica (SNAIP) for capillary electrochromatography (CEC). The unique structure of SNAIP contributed to the retention by three interactions including hydrophobic, electrostatic and S-S interactions and the acceleration of electroosmotic flow at an acidic condition. The CEC employing SNAIP was successively applied to the rapid separations of several drugs, peptides and polar compounds. Also, several examples for applying CEC to real sample analyses were demonstrated. Furthermore, with the idea to use adamantane as a shield to reduce the peak tailing of charged solutes in CEC, adamantyl (ADM)-functionalized polymer monolith by a single-step copolymerization with the monomer containing ADM structure and a cross-linker was presented. Three chiral stationary phases with different phenylalanine (Phe) peptide lengths, Phe 4 , Phe 8 , Phe 12 , were prepared to study the effect of peptide length on enantioseparation in reversed-phase HPLC. The highest resolution was observed for the selector with intermediate peptide length (i.e., Phe 8). The side chain of amino acids was also found to play a role for the separation performance of the chiral stationary phases (CSPs). The IR spectra suggested that the Phe peptides immobilized on the CSPs were assumed to be mainly in the D-helical state. Also, it was found that the conformation strongly contributed to the chiral recognition of the CSPs by thermodynamic study.

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“…Nowadays, a large diversity of CSPs is available to carry out enantioselective resolution. These CSPs mainly involve compounds such as cyclodextrins, polysaccharides, proteins, or peptide oligomers. − In the latter case, previous studies suggested that specific secondary structures, such as a helical conformation, can promote and enhance enantioselectivity. − In 2011, Wu et al investigated peptoids as a new class of chiral selector compounds in stationary phases . Peptoids are peptidomimetic molecules in which the side chain is appended to the nitrogen atom of the amide group instead of the carbon in the α-position to the amide carbonyl as it is the case in peptides .…”

Section: Introductionmentioning

confidence: 99%

Peptoids as a Chiral Stationary Phase for Liquid Chromatography: Insights from Molecular Dynamics Simulations

et al. 2021

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Peptoids are peptide regioisomers with attractive structural tunability in terms of sequence and three-dimensional arrangement. Peptoids are foreseen to have a great potential for many diverse applications, including their utilization as a chiral stationary phase in chromatography. To achieve chiral recognition, a chiral side chain is required to allow specific interactions with a given enantiomer from a racemic mixture. One of the most studied chiral stationary phases, built with (S)-N-1-phenylethyl (Nspe) units, was shown to be successful in resolving racemic mixtures of binaphthyl derivatives. However, there is currently no description at the atomic scale of the factors favoring its enantioselectivity. Here, we take advantage of steered molecular dynamics simulations to mimic the elution process at the atomic scale and present evidence that the predominantly right-handed helical conformation of Nspe peptoids and their ability to form stronger hydrogen bonds with the (S) enantiomer are responsible for the chiral recognition of the popular chiral probe 2,2′-bihydroxy-1,1′-binaphthyl.

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Effects of Temperature and Mobile Phase Condition on Chiral Recognition of Poly(l-phenylalanine) Chiral Stationary Phase

Cited by 4 publications

References 24 publications

Chiral ligand-exchange high-performance liquid chromatography with copper (II)-L-phenylalanine complexes for separation of 3,4-dimethoxy-α-methylphenylalanine racemes

Chiral ligand-exchange high-performance liquid chromatography with copper (II)-L-phenylalanine complexes for separation of 3,4-dimethoxy-α-methylphenylalanine racemes

Development and Pharmaceutical Applications of Functional Stationary Phases for Capillary Electrochromatography and Chiral Separation

Peptoids as a Chiral Stationary Phase for Liquid Chromatography: Insights from Molecular Dynamics Simulations

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