New CSPs based on peptidomimetics: efficient chiral selectors in enantioselective separations

Burguete, M. Isabel; Fréchet, Jean M. J.; García‐Verdugo, Eduardo; Jančo, Miroslav; Luis, Santiago V.; Švec, František; Vicent, Marı́a J.; Xu, Mingcheng

doi:10.1007/s00289-002-0005-3

Cited by 10 publications

(7 citation statements)

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“…This pseudodilution effect has been demonstrated by the results of several authors showing that the activity of different polymer-bound reagents and catalysts is increased by low levels of functionalization. 83,100,121 This is the case, for instance, of supported pseudopeptides 55 and 56 prepared by grafting onto gel-type resins, [122][123][124][125] whose copper complexes were studied for the catalytic cyclopropanation of styrene ( Fig. 8).…”

Section: Gel-type Polymeric Supportsmentioning

confidence: 99%

Chiral catalysts immobilized on achiral polymers: effect of the polymer support on the performance of the catalyst

et al. 2018

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Section: Gel-type Polymeric Supportsmentioning

confidence: 99%

Chiral catalysts immobilized on achiral polymers: effect of the polymer support on the performance of the catalyst

et al. 2018

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“…Highly cross-linked, permanently porous polymers are useful in a wide range of applications. − Unlike lightly cross-linked “gel-type” polymers which become porous when swollen by solvents, more highly cross-linked polymers have a permanent porous structure which is formed during their preparation and persists in the dry state . The internal porous morphology is characterized by interconnected channels (pores) which permeate the rigid, extensively cross-linked polymer matrix.…”

Section: Introductionmentioning

confidence: 99%

Structural Control in Porous Cross-Linked Poly(methacrylate) Monoliths Using Supercritical Carbon Dioxide as a “Pressure-Adjustable” Porogenic Solvent

et al. 2003

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The synthesis of permanently porous, highly cross-linked, poly(methacrylate) resins using supercritical CO 2 is described. The pressure-adjustable solvent properties associated with supercritical fluid solvents are exploited to fine-tune the average pore size and surface area of the materials. It was found that the materials' properties varied in a discontinuous manner with respect to the CO 2 pressure. A minimum in the BET surface area (and a maximum in the pore diameter) was observed at a reaction pressure of approximately 2600 psi. These trends were rationalized by the fact that the mechanisms of nucleation, aggregation, and pore formation are highly sensitive to the nature of the porogenic solvent environment.

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“…Synthetic peptide derivatives [17][18][19][20], macrocyclic (glyco)peptides [21,22] and peptidomimetics [23,24] were already earlier found to be of special interest as chiral SOs, covalently bonded to chromatographic support, for enantioselective chromatography. Other approaches utilized N-protected peptides as chiral counterions for enantioselective ion-pair HPLC or SFC [25][26][27][28].…”

Section: Introductionmentioning

confidence: 99%

Novel enantioselective strong cation exchangers based on sulfodipeptide selectors: Evaluation for enantiomer separation of chiral bases by nonaqueous capillary electrochromatography

et al. 2004

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Strong cation exchange (SCX)-type chiral stationary phases (CSPs) based on beta-amino sulfonic acid-terminated dipeptide derivatives as chiral selectors, immobilized on thiol-modified silica particles (3.5 microm), were synthesized and applied to enantiomer separations of chiral bases by nonaqueous capillary electrochromatography (CEC). The effect of structural variations of the sulfodipeptide selectors on the separation factors alpha was investigated. These studies included variation of the acid-terminal amino sulfonic acid residue, variation of the configurations, i.e., comparison of the diastereomeric (S,S)- and (R,S)-configurations of the sulfodipeptides, and finally comparison of sulfodipeptide selectors with corresponding beta-amino sulfonic acid analogs. In general, the capillary columns (100 microm ID) packed with the new SCX-type CSPs showed enantioselectivity for an elaborated set of chiral basic drugs in CEC acting by an enantioselective cation-exchange retention mechanism. N-[N-(4-Allyloxy-3,5-dichlorobenzoyl)-leucyl]-2-amino-3,3-dimethylbutane sulfonic acid, in particular with (R,S)-configuration, turned out to be a more effective SCX-type selector than a more rigid analog based on N-[N-(4-Allyloxy-3,5-dichlorobenzoyl)-leucyl]-2-pyrrolidinemethane sulfonic acid. Both of the former diastereomers were capable to baseline-resolve the enantiomers of ca. 40% of the tested basic chiral solutes including sympathomimetics and beta-blockers, while for the latter SCX-type CSPs only 10-20% of the selected solutes afforded resolutions > 1.5.

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New CSPs based on peptidomimetics: efficient chiral selectors in enantioselective separations

Cited by 10 publications

References 1 publication

Chiral catalysts immobilized on achiral polymers: effect of the polymer support on the performance of the catalyst

Chiral catalysts immobilized on achiral polymers: effect of the polymer support on the performance of the catalyst

Structural Control in Porous Cross-Linked Poly(methacrylate) Monoliths Using Supercritical Carbon Dioxide as a “Pressure-Adjustable” Porogenic Solvent

Novel enantioselective strong cation exchangers based on sulfodipeptide selectors: Evaluation for enantiomer separation of chiral bases by nonaqueous capillary electrochromatography

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