Comparison of three chiral stationary phases with respect to their enantio- and diastereoselectivity for cyclic β-substituted α-amino acids

Schlauch, Michael; Kos, Olha; Frahm, A. W.

doi:10.1016/s0731-7085(01)00587-8

Cited by 16 publications

(9 citation statements)

References 34 publications

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“…[26][27][28] Besides complex formation, additional interactions (e.g., hydrogen bonding, hydrophobic interactions) may contribute to the separation of the enantiomers, and steric reasons may also have crucial effect on the elution order. 6 It can be assumed that the pencillamine (fixed on the silicagel) interacts with copper(II) through the amino and carboxyl groups, 11 while the stereoisomers of the analyte occupy the remaining two positions (the coordination of water molecules may be involved in the case of octahedral complex formations).…”

Section: Resultsmentioning

confidence: 99%

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High‐performance liquid chromatographic enantioseparation of unusual secondary amino acids on a D‐penicillamine‐based chiral ligand exchange column

Ilisz¹,

Tourwé²,

Armstrong³

et al. 2006

Chirality

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The application of a chiral ligand-exchange column (CLEC) for the direct high-performance liquid chromatographic enantioseparation of unusual secondary amino acids using D-penicillamine-Cu(II) complex as chiral selector is reported. The amino acids investigated were pyrrolidine-2-carboxylic acid, piperidine-2-carboxylic acid, piperazine-2-carboxylic acid, morpholine-3-carboxylic acid, and thiomorpholine-3-carboxylic acid analogs. Chromatographic results are given as the retention, separation, and resolution factors. The chromatographic conditions were varied to achieve optimal separation. The elution sequence of the enantiomers was determined and in most cases the S isomer eluted before R.

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Section: Resultsmentioning

confidence: 99%

“…28 The incorporation of another heteroatom (N, O, or S) in the ring caused rather varying retention behavior, which may be associated with the differing complexation behavior of the hetero atoms or with the ability for further secondary interactions of the second heteroatom.…”

Section: Resultsmentioning

confidence: 99%

High‐performance liquid chromatographic enantioseparation of unusual secondary amino acids on a D‐penicillamine‐based chiral ligand exchange column

Ilisz¹,

Tourwé²,

Armstrong³

et al. 2006

Chirality

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“…2-Piperidinecarboxylic acid (pipecolic acid) enantiomers in plasma and commercially available Arg enantiomers were separated by Aboul-Enein et al [64,65] on T-A 2-2 in RPM, and their method was successfully used for enantiomeric purity determination. Schlauch et al [66,67] investigated the influence of the mobile phase composition and pH on the enantioseparation of several cyclic b-substituted a-amino acids on T-A 2-2 . It was found that the discrimination mechanism for the enantiomers and diastereomers (amino acids with two chiral centers) differed, probably in consequence of the different effects caused by the changes in the conformation of teicoplanin.…”

Section: Enantioseparation Of Nonprotected Protein and Unusual Amino mentioning

confidence: 99%

HPLC separation of amino acid enantiomers and small peptides on macrocyclic antibiotic‐based chiral stationary phases: A review

Ilisz

Berkecz

Péter

2006

J of Separation Science

158

105

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The search for new and effective chiral selectors capable of separating a wide variety of enantiomeric compounds is an ongoing process. In the past decade, macrocyclic antibiotics have proved to be an exceptionally useful class of chiral selectors for the separation of enantiomers of biological and pharmacological importance by means of HPLC, TLC and electrophoresis. More chiral analytes have been resolved through the use of glycopeptides than with all the other macrocyclic antibiotics combined (ansamycins, thiostrepton, aminoglycosides, etc.). The glycopeptides avoparcin, teicoplanin, ristocetin A and vancomycin have been extensively used as chiral selectors in the form of chiral bonded phases in HPLC, and HPLC stationary phases based on these glycopeptides have been commercialized. Teicoplanin, vancomycin, their analogs and ristocetin A seem to be the most useful glycopeptide HPLC bonded phases for the enantioseparation of proteins and unusal native and derivatized amino acids. In fact, the macrocyclic glycopeptides are to some extent complementary to one another: where partial enantioresolution is obtained with one glycopeptide, there is a high probability that baseline or better separation can be obtained with another. This review sets out to characterize the physicochemical properties of these antibiotics and their application in the enantioseparations of amino acids. The mechanism of separation, the sequence of elution of the stereoisomers and the relation to the absolute configuration are also discussed.

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“…Different enantiomers of various amines and amino acids may possess different biological activities; therefore, the determination of the enantiomeric composition of these organic compounds is of great importance, especially in the pharmaceutical, pesticide, food, and cosmetic industries. Since the seminal work of Cram and coworkers, a large number of different chiral crown ethers have been synthetized and studied for their enantiomeric recognition ability toward the enantiomers of protonated chiral primary amines, amino acids, and their derivates …”

Section: Introductionmentioning

confidence: 99%

Synthesis and pK_a determination of new enantiopure dimethyl‐substituted acridino‐crown ethers containing a carboxyl group: Useful candidates for enantiomeric recognition studies

et al. 2017

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New enantiopure dimethyl-substituted acridino-18-crown-6 and acridino-21-crown-7 ethers containing a carboxyl group at position 9 of the acridine ring [(S,S)-8, (S,S)-9, (R,R)-10] were synthesized. The pK values of the new crown ethers [(S,S)-8, (S,S)-9, (R,R)-10] and of an earlier reported macrocycle [(R,R)-2] were determined by UV-pH titrations. Crown ether (S,S)-8 was attached to silica gel by covalent bonds and the enantiomeric separation ability of the newly prepared chiral stationary phase [(S,S)-CSP-12] was studied by high-performance liquid chromatography (HPLC). Homochiral preference was observed and the best separation was achieved for the enantiomers of 1-NEA. Ligands (S,S)-9 and (R,R)-10 are precursors of enantioselective sensor and selector molecules for the enantiomers of protonated primary amines, amino acids, and their derivatives.

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Comparison of three chiral stationary phases with respect to their enantio- and diastereoselectivity for cyclic β-substituted α-amino acids

Cited by 16 publications

References 34 publications

High‐performance liquid chromatographic enantioseparation of unusual secondary amino acids on a D‐penicillamine‐based chiral ligand exchange column

High‐performance liquid chromatographic enantioseparation of unusual secondary amino acids on a D‐penicillamine‐based chiral ligand exchange column

HPLC separation of amino acid enantiomers and small peptides on macrocyclic antibiotic‐based chiral stationary phases: A review

Synthesis and pK_a determination of new enantiopure dimethyl‐substituted acridino‐crown ethers containing a carboxyl group: Useful candidates for enantiomeric recognition studies

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Comparison of three chiral stationary phases with respect to their enantio- and diastereoselectivity for cyclic β-substituted α-amino acids

Cited by 16 publications

References 34 publications

High‐performance liquid chromatographic enantioseparation of unusual secondary amino acids on a D‐penicillamine‐based chiral ligand exchange column

High‐performance liquid chromatographic enantioseparation of unusual secondary amino acids on a D‐penicillamine‐based chiral ligand exchange column

HPLC separation of amino acid enantiomers and small peptides on macrocyclic antibiotic‐based chiral stationary phases: A review

Synthesis and pKa determination of new enantiopure dimethyl‐substituted acridino‐crown ethers containing a carboxyl group: Useful candidates for enantiomeric recognition studies

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Synthesis and pK_a determination of new enantiopure dimethyl‐substituted acridino‐crown ethers containing a carboxyl group: Useful candidates for enantiomeric recognition studies