Enantioseparation of kavain on Chiralpak IA under normal‐phase, polar organic and reversed‐phase conditions

Cirilli, Roberto; Ferretti, Rosella; Gallinella, Bruno; Bilia, Anna Rita; Vincieri, Franco Francesco; Torre, Francesco La

doi:10.1002/jssc.200800044

Cited by 21 publications

(9 citation statements)

References 30 publications

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“…Thus, in the first step of this study, the enantioseparability of the selected bipyridines on Chiralpak IA and Chiralpak IC was tested under the same elution conditions (Table ) and a comparison between the behaviors of the two immobilized columns was made. In particular, Chiralpak IA is the immobilized version of Chiralpak AD‐H, so we were interested to verify the performance of the immobilized column compared to the coated one . In fact, under the same chromatographic conditions, the enantioselectivity of the immobilized CSPs can change compared to the coated CSPs: higher selectivity values can sometimes be achieved on the immobilized CSPs but, in other cases, the enantioselectivity tends to decrease .…”

Section: Resultsmentioning

confidence: 99%

Optimization of the HPLC enantioseparation of 3,3′-dibromo-5,5′-disubstituted-4,4′-bipyridines using immobilized polysaccharide-based chiral stationary phases

et al. 2013

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The HPLC enantioseparation of nine atropisomeric 3,3',5,5'-tetrasubstituted-4,4'-bipyridines was performed in normal and polar organic (PO) phase modes using two immobilized polysaccharide-based chiral columns, namely, Chiralpak IA and Chiralpak IC. The separation of all racemic analytes, the effect of the chiral selector, and mobile phase (MP) composition on enantioseparation and the enantiomer elution order (EEO) were studied. The beneficial effect of nonstandard solvents, such as tetrahydrofuran (THF), dichloromethane (DCM), and methyl t-butyl ether on enantioseparation was investigated. All selected 4,4'-bipyridines were successfully enantioseparated on Chiralpak IA under normal or PO MPs with separation factors from 1.14 to 1.70 and resolutions from 1.3 to 6.5. Two bipyridines were enantioseparated at the multimilligram level on Chiralpak IA. Differently, Chiralpak IC was less versatile toward the considered class of compounds and only five bipyridines out of nine could be efficiently separated. In particular, on these columns, the ternary mixture n-heptane/THF/DCM (90:5:5) as MP had a positive effect on enantioseparation. An interesting phenomenon of reversal of the EEO depending on the composition of the MP for the 3,3'-dibromo-5,5'-bis-(E)-phenylethenyl-4,4'-bipyridine along with an exceptional enantioseparation for the 3,3'-dibromo-5,5'-bis-ferrocenylethynyl-4,4'-bipyridine (α = 8.33, R(s) = 30.6) were observed on Chiralpak IC.

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Section: Resultsmentioning

confidence: 99%

Optimization of the HPLC enantioseparation of 3,3′-dibromo-5,5′-disubstituted-4,4′-bipyridines using immobilized polysaccharide-based chiral stationary phases

et al. 2013

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“…Moreover, different solvents can alter the steric structure of the polymer backbone and the binding sites inside the chiral groove, providing different selectivity on the same CSPs. For this reason, the multimodal approach is of great usefulness for method development on polysaccharide‐based CSPs because it expands the applicability of these phases for chiral separation .…”

Section: Introductionmentioning

confidence: 99%

High‐performance liquid chromatography enantioseparation of polyhalogenated 4,4′‐bipyridines on polysaccharide‐based chiral stationary phases under multimodal elution

Peluso

Mamane

Aubert

et al. 2014

J of Separation Science

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An investigation on the high-performance liquid chromatography enantioseparation of 12 polyhalogenated 4,4'-bipyridines on polysaccharide-based chiral stationary phases is described. The overall study was directed toward the generation of efficient separations in order to obtain pure atropisomers that will serve as ligands for building homochiral metal organic frameworks. Four coated columns--namely, Lux Cellulose-1, Lux Cellulose-2, Lux Cellulose-4, and Lux Amylose-2--and two immobilized columns--namely, Chiralpak IC and IA--were used under normal, polar organic, and reversed-phase elution modes. Moreover, Chiralcel OJ was considered under normal-phase and polar organic conditions. The effect of the chiral selector and mobile phase composition on the enantioseparation, the enantiomer elution order and the beneficial effect of nonstandard solvents were studied. The effect of water in the mobile phase on the enantioselectivity and retention was investigated and retention profiles typical of hydrophilic interaction liquid chromatography were observed. Interesting phenomena of solvent-induced enantiomer elution order reversal occurred under normal-phase mode. All the considered 4,4'-bipyridines were enantioseparated at the multimilligram level.

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“…In 1998 Prof. Maria Camilla Bergonzi joined the group in order to start her PhD and during the following years, first as a post-doc and since 2005 as an aggregate professor, she has strongly supported my research. Authentication, quality control and stability testing have largely been performed using not only conventional [54][55][56][57][58][59][60][61][62][63][64][65][66][67][68][69][70][71][72] Our publications represented the first studies on the stability and compatibility with excipients of important dried commercial extracts, such as St. John's wort (SJW), and results were dramatic when the studies were carried out using ICH guidelines [56]. Other studies reported on the quality and/or stability of decoctions, teas and infusions, aromatic waters, tinctures and mother tinctures, commercial instant teas of common herbal drugs and obtained important information about their preparation, content and shelf-lives.…”

Section: S Telephium (Crassulaceae) (mentioning

confidence: 99%

1968–2008: 40 Years of Franco F. Vincieri's Natural Products Research

Bilia

2008

Natural Product Communications

Self Cite

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This paper presents an overview of Prof. Vincieri's accomplishments in his career as a researcher in the field of pharmacognosy (pharmaceutical biology), analytical phytochemistry and pharmaceutical technology applied to herbal drug preparations at the Department of Pharmaceutical Sciences of the University of Florence. This article is a recognition of his valuable contributions to these research fields, especially for his outstanding and innovative interdisciplinary studies on the quality control of herbal drugs, herbal drug preparations, herbal medicinal products, botanical food supplements, and some "special foods" such as grapes, wines, olives and olive oil.

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Enantioseparation of kavain on Chiralpak IA under normal‐phase, polar organic and reversed‐phase conditions

Cited by 21 publications

References 30 publications

Optimization of the HPLC enantioseparation of 3,3′-dibromo-5,5′-disubstituted-4,4′-bipyridines using immobilized polysaccharide-based chiral stationary phases

Optimization of the HPLC enantioseparation of 3,3′-dibromo-5,5′-disubstituted-4,4′-bipyridines using immobilized polysaccharide-based chiral stationary phases

High‐performance liquid chromatography enantioseparation of polyhalogenated 4,4′‐bipyridines on polysaccharide‐based chiral stationary phases under multimodal elution

1968–2008: 40 Years of Franco F. Vincieri's Natural Products Research

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