Comparison of Separation Efficiency of Macrocyclic Glycopeptide-Based Chiral Stationary Phases for the LC Enantioseparation of β-Amino Acids

Sztojkov‐Ivanov, Anita; Lázár, László; Fülöp, Ferenc; Armstrong, Daniel W.; Péter, Antal

doi:10.1365/s10337-006-0824-8

Cited by 29 publications

(21 citation statements)

References 30 publications

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“…Many investigations were done to understand and to optimize the chiral separation properties of this recent class of chiral selectors. 6,[8][9][10][11] This work focuses on the separation mechanism of the commercially available macrocyclic glycopeptidebased CSPs. Table 1 compares the physicochemical properties of ristocetin A, teicoplanin, its aglycon and vancomycin, the four macrocyclic glycopeptide antibiotics used in commercially available CSPs.…”

Section: Introductionmentioning

confidence: 99%

Chiral recognition mechanisms with macrocyclic glycopeptide selectors

Berthod

2008

Chirality

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Macrocyclic glycopeptide selectors are naturally occurring antibiotics produced by microorganisms. They were found to be excellent chiral selectors for a wide range of enantiomers, including amino acids. Four selectors are commercialized as chiral stationary phases (CSP) for chromatography. They are ristocetin, teicoplanin, vancomycin, and the teicoplanin aglycone (TAG). The key docking interaction for amino acid recognition was established to be a charge-charge interaction between the anionic carboxylate group of the amino acid and a cationic amine group of the macrocyclic peptidic selector basket. The carbohydrate units are responsible for secondary interactions. However, they hinder somewhat the charge-charge docking interaction. The TAG selector is more effective for amino acid enantioseparations than the other CSPs. The "sugar" units are however useful allowing for chiral recognitions of other analytes, e.g., beta-blockers, not possible with the aglycone. Thermodynamic studies established that normal phase and reversed phase enantioseparations were enthalpy-driven. With polar waterless mobile phases used in the polar ionic mode, some separations were enthalpy-driven and others were entropy-driven. The linear solvation energy method was tentatively used to gain knowledge about the chiral recognition mechanism. It appeared to be a viable approach with neutral molecules but it failed with ionizable solutes. With molecular solutes and the teicoplanin CSP, the study showed a significant role of the surface charge-induced dipole interaction and steric effects. The remarkable complementary enantioselectivity effect observed with the four CSPs is discussed.

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Section: Introductionmentioning

confidence: 99%

Chiral recognition mechanisms with macrocyclic glycopeptide selectors

Berthod

2008

Chirality

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“…Similar results were observed in this study for monoterpene-based analogues and -amino acids [62,[137][138][139][140].…”

Section: Effects Of the Nature Of The Mobile Phasesupporting

confidence: 91%

High-performance liquid chromatographic enantioseparation of unnatural b-amino acids on chiral stationary phases

Sípos

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“…On a CSP containing an A-40.926 glycopeptide, D'Acquarica 8 observed somewhat higher retention factors for alicyclic and cyclic b-amino acids on the aglycone CSP than on the native glycopeptide. Similarly, Pé ter and coworkers 11,12,14,44,45 observed that for b-3-homoamino acids the retention factors were higher on the teicoplanin aglycone CSP.…”

Section: Results and Discussion Separation Of Enantiomers On Chirobiomentioning

confidence: 73%

“…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. 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 Chirobiomentioning

confidence: 99%

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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Comparison of Separation Efficiency of Macrocyclic Glycopeptide-Based Chiral Stationary Phases for the LC Enantioseparation of β-Amino Acids

Cited by 29 publications

References 30 publications

Chiral recognition mechanisms with macrocyclic glycopeptide selectors

Chiral recognition mechanisms with macrocyclic glycopeptide selectors

High-performance liquid chromatographic enantioseparation of unnatural b-amino acids on chiral stationary phases

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

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Comparison of Separation Efficiency of Macrocyclic Glycopeptide-Based Chiral Stationary Phases for the LC Enantioseparation of β-Amino Acids

Cited by 29 publications

References 30 publications

Chiral recognition mechanisms with macrocyclic glycopeptide selectors

Chiral recognition mechanisms with macrocyclic glycopeptide selectors

High-performance liquid chromatographic enantioseparation of unnatural b-amino acids on chiral stationary phases

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

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Product

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