Direct high-performance liquid chromatographic separation of unusual secondary amino acids and a comparison of the performances of Chirobiotic T and TAG columns

Péter, Antal; Török, Roland; Armstrong, Daniel W.

doi:10.1016/j.chroma.2004.09.027

Cited by 29 publications

(15 citation statements)

References 28 publications

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“…12,45 The elution sequences for 1, 2, 5, and 6 were determined on all three Chirobiotic CSPs; in all cases, the elution sequence R < S was observed. This differs from the result for a-amino acids, [46][47][48][49] whereas for b-3-homoamino acids 9-13 with one chiral center both S < R and R < S elution sequences were observed.…”

Section: Results and Discussion Separation Of Enantiomers On Chirobiocontrasting

confidence: 99%

“…In general, it seems that the steric hindrance effect of the sugar moieties was predominant for the b 2 -homoamino acids. Better enantioseparations of the enantiomers of aamino acids, cyclic-b-amino acids, and secondary amino acids were observed on the teicoplanin aglycone CSP, 14,42,44,47 but for b-3-homoamino acids better separation was found on native teicoplanin. 12,45 The elution sequences for 1, 2, 5, and 6 were determined on all three Chirobiotic CSPs; in all cases, the elution sequence R < S was observed.…”

Section: Results and Discussion Separation Of Enantiomers On Chirobiomentioning

confidence: 94%

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High‐performance liquid chromatographic chiral separation of β²‐homoamino acids

et al. 2008

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Reversed-phase high-performance liquid chromatographic methods were developed for the separation of enantiomers of eleven unnatural beta(2)-homoamino acids on chiral stationary phases containing macrocyclic glycopeptides (teicoplanin-containing Chirobiotic T and T2) or the macrocyclic peptide teicoplanin aglycone (Chirobiotic TAG) as chiral selectors. The effects of the organic modifier, the mobile phase composition, temperature, and the structures of the analytes on the separations were investigated. Separations were carried out at constant mobile phase compositions in temperature range 7-45 degrees C and the changes in enthalpy, Delta(DeltaH(o)), entropy, Delta(DeltaS(o)), and free energy, Delta(DeltaG(o)), were calculated. The -Delta(DeltaG(o)) values obtained on the three columns indicated that Chirobiotic TAG, without sugar units, may promote the interactions of the enantiomers of beta(2)-homoamino acids with branched alkyl or aryl side-chains, whereas for beta(2)-homoamino acids with alkyl side-chains Chirobiotic T and T2 seem to be more favorable. The elution sequence was determined in some cases and was observed to be R < S.

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Section: Results and Discussion Separation Of Enantiomers On Chirobiocontrasting

confidence: 99%

Section: Results and Discussion Separation Of Enantiomers On Chirobiomentioning

confidence: 94%

High‐performance liquid chromatographic chiral separation of β²‐homoamino acids

et al. 2008

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“…They also concluded that sugar moieties can contribute significantly to the resolution of a number of non-amino acid enantiomeric pairs. PØter et al [79,80] CSPs for a series of unusual a-and b-amino acids. For comparison purposes, the same mobile phase composition was used on the two selectors.…”

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

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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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“…[1][2][3][4] On the contrary, the enantiomer separation of free amino acids with nonderivatized (nonprotected) amino groups is much more challenging. LC methods of choice for this task make use of teicoplanin or teicoplanin aglycone CSPs (Chirobiotic T and TAG, respectively), [8][9][10][11] chiral ligand exchange chromatography systems, [12][13][14][15] or chiral crown ether CSPs. [16][17][18] Underivatized amino acids endowed with specific physicochemical features such as the presence of an additional ionizable group and/or particularly bulky portions can also be resolved on quinine and quinidine carbamate CSPs (Chiralpak QN-AX and QD-AX, respectively).…”

Section: Introductionmentioning

confidence: 99%

Enantioselective HPLC of potentially CNS‐active acidic amino acids with a cinchona carbamate based chiral stationary phase

et al. 2008

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A tert-butylcarbamoylquinine-based chiral stationary phase (Chiralpak QN-AX) has been employed for the enantiomer separation of underivatized chiral acidic amino acids, viz. 4-carboxyphenylalanine (4-CPHE), 1-aminoindan-1,5-dicarboxylic acid (AIDA), 2-(5-carboxy-3-methyl-2-thienyl)glycine (3-MATIDA), 2-(4-carboxy-5-methyl-2-thienyl)glycine (5-MATIDA), and 2-(2'-carboxy-3'-phenylcyclopropyl)glycine (PCCG). Some of the acidic amino acids have potential activity on the central nervous system and are thus of great interest. A stereoselective HPLC method that allows the baseline resolution of all the five test solutes has been developed. For that purpose the mobile phase composition (pH, organic modifier, and type) and flow rate were optimized. The final method makes use of mild elution conditions, namely methanol - 0.8 M ammonium acetate buffer (97.5:2.5; v/v) pH 5.5 which are also compatible with mass spectrometric detection.

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Direct high-performance liquid chromatographic separation of unusual secondary amino acids and a comparison of the performances of Chirobiotic T and TAG columns

Cited by 29 publications

References 28 publications

High‐performance liquid chromatographic chiral separation of β²‐homoamino acids

High‐performance liquid chromatographic chiral separation of β²‐homoamino acids

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

Enantioselective HPLC of potentially CNS‐active acidic amino acids with a cinchona carbamate based chiral stationary phase

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Direct high-performance liquid chromatographic separation of unusual secondary amino acids and a comparison of the performances of Chirobiotic T and TAG columns

Cited by 29 publications

References 28 publications

High‐performance liquid chromatographic chiral separation of β2‐homoamino acids

High‐performance liquid chromatographic chiral separation of β2‐homoamino acids

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

Enantioselective HPLC of potentially CNS‐active acidic amino acids with a cinchona carbamate based chiral stationary phase

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High‐performance liquid chromatographic chiral separation of β²‐homoamino acids

High‐performance liquid chromatographic chiral separation of β²‐homoamino acids