Preparation of HPLC chiral packing materials using cellulose tris(4‐methylbenzoate) for the separation of chrysanthemate isomers

Yamamoto, Chiyo; Yamada, Kenji; Motoya, Kahori; Kamiya, Yuichiro; Kamigaito, Masami; Aratani, Tadatoshi

doi:10.1002/pola.21620

Cited by 23 publications

(27 citation statements)

References 25 publications

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“…Understanding of chiral recognition mechanisms in play with these materials is very important as it can lead to the design of new, even more effective chiral selectors, as well as for the optimization of separations with existing CSPs. Numerous studies have been performed in the past for getting insight into intermolecular interactions involved in analyte–selector interactions with polysaccharide derivatives . Several instrumental techniques as well as molecular mechanics calculations and statistical methods have been applied in these studies.…”

Section: Introductionmentioning

confidence: 99%

HPLC separation of dihydropyridine derivatives enantiomers with emphasis on elution order using polysaccharide‐based chiral columns

Jibuti

Mskhiladze

Takaishvili

et al. 2012

J of Separation Science

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The separation of enantiomers of five chiral dihydropyridine derivatives was studied on five different polysaccharide-based chiral HPLC columns with various normal-phase (NP), polar organic, and reversed-phase eluents. Along with the successful separation of analyte enantiomers, the emphasis of this study was on enantiomer elution order (EEO) with various columns and mobile phase composition. The interesting phenomenon of reversal of EEO, recently reported in the case of amlodipine (AML) depending on the concentration of formic acid in acetonitrile, was also confirmed with NP eluents. Under RP conditions at relatively low water content, the EEO of AML could also be reverted by varying the concentration of formic acid in the mobile phase. However, at higher water content the same parameter did not affect the EEO, but only induced gradual decrease in resolution up to complete co-elution of enantiomers. Additionally, in organic-aqueous mobile phases retention factors decreased with increasing water content but only up to 20% (v/v), while above this concentration the expected typical RP behavior was observed. The presence of the commonly used additive diethylamine in the mobile phase seems important for observing a reversal in EEO with increasing concentration of formic acid. The reversal of the EEO was characteristic of AML only and was not observed for any of other dihydropyridines included in this study.

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Section: Introductionmentioning

confidence: 99%

HPLC separation of dihydropyridine derivatives enantiomers with emphasis on elution order using polysaccharide‐based chiral columns

Jibuti

Mskhiladze

Takaishvili

et al. 2012

J of Separation Science

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“…The four polysaccharide CSP-based HPLC columns, Chiralpak AS, Chiralpak AD, Chiralcel OD and Chiralcel OJ, have been reported to offer the highest degree of stereogenic recognition for a large number of chiral compounds. [24][25][26][27][28][29][30][31] Relative selectivity of the enantiomers of the three imidazolinones was first examined on these columns. The initial column screening was conducted under the same chromatographic conditions, with a mobile phase of n-hexane/2-propanol/acetic acid (85/ 15/0.1, v/v/v) at a flow rate of 0.8 ml min À1 and temperature of 258C.…”

Section: Results and Discussion Chiral Separation On Different Cspsmentioning

confidence: 99%

Enantiomeric separation of imidazolinone herbicides using chiral high‐performance liquid chromatography

Lin

Zhou

et al. 2006

Chirality

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Chiral high-performance liquid chromatography (HPLC) is one of the most powerful tools to prepare enantiopure standards of chiral compounds. In this study, the enantiomeric separation of imidazolinone herbicides, i.e., imazethapyr, imazapyr, and imazaquin, was investigated using chiral HPLC. The enantioselectivity of Chiralpak AS, Chiralpak AD, Chiralcel OD, and Chiralcel OJ columns for the three analytes was compared under similar chromatographic conditions. Chiralcel OJ column showed the best chiral resolving capacity among the test columns. The resolved enantiomers were distinguished by their signs of circular dichroism detected at 275 nm and their structures confirmed with LC-mass spectrometric analysis. Factors affecting the chiral separation of imidazolinones on Chiralcel OJ column were characterized. Ethanol acted as a better polar modifier than the other alcohols including 2-propanol, 1-butanol, and 1-pentanol. Although the acidic modifier in the mobile phase did not influence chiral recognition, it was necessary for reducing the retention time of enantiomers and suppressing their peak tailing. Thermodynamic evaluation suggests that enantiomeric separation of imidazolinones on Chiralcel OJ column is an enthalpy-driven process from 10 to 408C. This study also shows that small amounts of pure enantiomers of imidazolinones may be obtained by using the analytical chiral HPLC approach.

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“…Figure 3 shows a chromatogram of the resolution of 10 on the CSP prepared from amylose cinnamate (3a Table 2. 25 The chiral recognition ability was sensitive to the main-chain structures of polysaccharides. CSP 1a showed almost no chiral recognition ability, in contrast to CSP 7, which had the same side chain as CSP 1a and could separate eight kinds of racemates.…”

Section: Results and Discussion Enantioseparation On Amylose Estersmentioning

confidence: 99%

“…19,20,25,27,28 Recently, we reported that the recognition ability of cellulose 4-methylbenzoate 7 can be controlled using additives when the derivative is coated on silica gel. 25 This suggests that the higher-order structure of cellulose esters on silica gel probably varies depending on the coating conditions.…”

Section: Influence Of Additivesmentioning

confidence: 99%

Enantioseparation using amylose esters as chiral stationary phases for high-performance liquid chromatography

Sugiura

Yamamoto

Ikai

et al. 2010

Polym J

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Novel amylose ester derivatives were synthesized and their chiral recognition abilities as chiral stationary phases for highperformance liquid chromatography were evaluated. Compared with amylose benzoate derivatives, cinnamate derivatives showed a higher chiral recognition ability and some racemates could be efficiently resolved. The recognition abilities of these derivatives varied significantly depending on the types and positions of substituents introduced into the phenyl group. Among the prepared derivatives, the nonsubstituted cinnamate derivative showed a relatively high chiral recognition, and interestingly, its ability was influenced by the preparation conditions of packing materials using silica gel as a support.

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Preparation of HPLC chiral packing materials using cellulose tris(4‐methylbenzoate) for the separation of chrysanthemate isomers

Cited by 23 publications

References 25 publications

HPLC separation of dihydropyridine derivatives enantiomers with emphasis on elution order using polysaccharide‐based chiral columns

HPLC separation of dihydropyridine derivatives enantiomers with emphasis on elution order using polysaccharide‐based chiral columns

Enantiomeric separation of imidazolinone herbicides using chiral high‐performance liquid chromatography

Enantioseparation using amylose esters as chiral stationary phases for high-performance liquid chromatography

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