Quinine- versus carbamoylated quinine-based chiral anion exchangers

Mandl, Alexandra; Nicoletti, Lorenzo; Lämmerhofer, Michael; Lindner, Wolfgang

doi:10.1016/s0021-9673(99)00803-1

Cited by 160 publications

(78 citation statements)

References 11 publications

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“…Cinchona alkaloids are commercially available and represent an interesting group of organic compounds, widely used as resolving agents for chiral acids, 13 N-derivatized amino acid, 14 binaphtols, 15 oligopeptides. 16 Structurally, they consist of a planar quinoline and rigid quinuclidine rings, which are connected by a secondary methyl alcohol bridge.…”

Section: Introductionmentioning

confidence: 99%

Enantioselective transport of D,L-phenylalanine and D,L-phenylglycine through a bulk liquid membrane containing cinchona alkaloid derivatives as chiral selectors

Canepari

Girelli

Mattei

et al. 2009

J. Braz. Chem. Soc.

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Diversos derivados de Cinchona foram testados como carregadores quirais móveis, para o transporte enantiosseletivo de D,L-fenilglicina e D,L-fenilalanina, através de uma membrana líquida orgânica volumosa (MLV). Os efeitos de vários parâmetros, como natureza do carregador, concentrações do solvente na membrana, do tampão, do soluto e do carregador, no enriquecimento quiral da MLV, foram avaliados. Somente a D,L-fenilglicina foi sujeita, em certo grau, ao transporte enantiosseletivo; a razão máxima de enantiosseletividade (as taxas de transporte iniciais do enantiômero L relativo ao antípoda) foi obtida empregando brometo de O-alil-N-(9-antracenilmetil) cinchonidínio como carregador. Em todos os casos, a seletividade mais alta foi observada durante os estágios iniciais do processo, indicando a taxa de aminoácido liberada da fase fonte (FF) para a fase orgânica da membrana (FM), como fator dirigente. O enriquecimento quiral pareceu depender mais de fatores termodinâmicos do que dos cinéticos, uma vez que a formação do complexo foi observada na interface (FF)/FM), enquanto a decomposição do complexo foi evidenciada na interface (FR)/(FM), onde FR é a fase receptora. O último fenômeno foi promovido pela presença de íons H + na FR. Different cinchona derivatives were tested as chiral mobile carriers for enantioselective transport of D,L-phenylglycine and D,L-phenylalanine through a bulk organic liquid membrane (BLM).The effects of several parameters such as carrier nature, membrane solvent, buffer, solute and carrier concentrations on BLM enrichment were evaluated. Only D,L-phenylglycine is subjected to enantioselective transport at a certain degree; the maximum enantioselectivity ratio (the initial transport rates of the L-enantiomer relative to the antipode) was reached by employing O-allyl-N-(9-anthracenylmethyl)cinchonidinium bromide as carrier. In all cases the highest selectivity was observed during the initial stages of the process, indicating the rate of amino acid release from the source phase (SP) to the membrane organic phase (MP) as the driving factor. Chiral enrichment appeared to depend on thermodynamic factors more than on kinetic ones, since the complex formation was observed at (SP)/MP) interface, while complex decomposition was evidenced at (RP)/(MP) interface, where RP is receiving phase. The last phenomenon was promoted by H + ions present in the RP.

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Section: Introductionmentioning

confidence: 99%

Enantioselective transport of D,L-phenylalanine and D,L-phenylglycine through a bulk liquid membrane containing cinchona alkaloid derivatives as chiral selectors

Canepari

Girelli

Mattei

et al. 2009

J. Braz. Chem. Soc.

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“…It has been reported that the ion pairing between positively-charged tertiary amine moiety in the quinuclidine ring of CCND and negatively-charged carboxylate group in the amino acids and the π-π interaction between the quinoline ring of CCND and the phenyl ring of DL-Phe plays a crucial role in the chiral selectivity of the cinchona alkaloids-based chiral column. 26,27 In the present condition, the best ion pairing and the π-π interaction would be attained at pH 5.0.…”

Section: Application To the Ot-cec Chiral Separation Of Amino Acidsmentioning

confidence: 66%

Open-tubular Electrochromatographic Chiral Separation of Amino Acids Using an Organic Nanocrystals Immobilized Capillary

et al. 2013

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“…Since introduction to the area of chiral separation, the chiral selectors obtained from the natural chiral pool, such as alkaloids [7][8][9][10], sterols [11][12][13], terpenoids [14], and tartaric acid derivatives [15], have proved their usefulness and value in HPLC, which are used as the chiral molecular recognition site of brush-type CSPs. As a new class of adsorbents, brush-type CSPs can be easily and selectively modified allowing a prompt evaluation of the structural changes on the adsorption process.…”

Section: Introductionmentioning

confidence: 99%

The synthesis and characterization of novel brush-type chiral stationary phase based on terpenoid selector for resolution of chiral drugs

Wang

Jia

Yao

et al. 2016

MATEC Web of Conferences

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Abstract. In the light of the chiral resolution mechanism and structures of brush-type CSP, a new chiral selector 4′-carboxyl-1′-ursolic methyl ester-3β-yl-benzoate has been prepared. Then the terpenoid chiral selector was covalently linked to 3-aminopropyl silica gel. Its structure identification data are provided by 1 H NMR, MS and elementary analysis. The enantiodiscriminating capability of the brush-type CSP was evaluated by static adsorption experiment with methyl mandelate, aniline derivative of mandelic acid, benzoin and ibuprofen. Experimental results demonstrated that the chiral selector has selectivity, and the enantiomers of methyl mandelate and ibuprofen could be separated on the CSP, which indicated that the novel brush-type CSP possess a bright prospects for chiral separation potentially.

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Quinine- versus carbamoylated quinine-based chiral anion exchangers

Cited by 160 publications

References 11 publications

Enantioselective transport of D,L-phenylalanine and D,L-phenylglycine through a bulk liquid membrane containing cinchona alkaloid derivatives as chiral selectors

Enantioselective transport of D,L-phenylalanine and D,L-phenylglycine through a bulk liquid membrane containing cinchona alkaloid derivatives as chiral selectors

Open-tubular Electrochromatographic Chiral Separation of Amino Acids Using an Organic Nanocrystals Immobilized Capillary

The synthesis and characterization of novel brush-type chiral stationary phase based on terpenoid selector for resolution of chiral drugs

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