Study of mechanisms of chiral discrimination of amino acids and their derivatives on a teicoplanin-based chiral stationary phase

Cavazzini, Alberto; Nadalini, Giorgio; Dondi, Francesco; Gasparrini, Francesco; Ciogli, Alessia; Villani, Claudio

doi:10.1016/j.chroma.2003.10.090

Cited by 104 publications

(72 citation statements)

References 55 publications

(104 reference statements)

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“…36 , and a values for 9 were higher than those for 8, especially on the Chirobiotic TAG column (Table 1 and Fig. 5).…”

Section: Results and Discussion Separation Of Enantiomers On Chirobiomentioning

confidence: 54%

“…[26][27][28][29] Accordingly, the column temperature has often been optimized in enantioselective HPLC separations. [30][31][32][33][34][35][36] The dependence of the retention of an analyte on the temperature can be expressed by the van't Hoff equation, which may be interpreted in terms of mechanistic aspects of chiral recognition:…”

Section: Introductionmentioning

confidence: 99%

“…[26][27][28][29][30][31][32][33][34][35][36] After the immobilization of selector molecules on CSPs, they exhibit enantioselective (s) and nonenantioselective (ns) adsorption sites, both of which can contribute to the overall retention factors (k 0 app ) of the enantiomers:…”

Section: Introductionmentioning

confidence: 99%

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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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“…36 , and a values for 9 were higher than those for 8, especially on the Chirobiotic TAG column (Table 1 and Fig. 5).…”

Section: Results and Discussion Separation Of Enantiomers On Chirobiomentioning

confidence: 54%

Section: Introductionmentioning

confidence: 99%

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

et al. 2008

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“…Cavazzini et al [119] studied the mechanism of chiral discrimination of amino acids and their N-acylated derivatives on T-A 2-2 , and formulated some general conclusions: (i) the importance of the formation of the complex between the carboxylic moiety of the enantiomer and the aglycone basket; (ii) formation of a H-bond between the amidic hydrogen of the acylated analyte and an amidic group on the stationary phase is pivotal for the stability of the complex aglycone D-enantiomer; (iii) esterification leads to complete loss of the apparent enantioselectivity; (iv) one or both enantiomers can be excluded from the selector owing to ionic interactions between the CSP, the analytes and the surrounding medium and/or a steric hindrance effect; (v) selection appears better for MeOH as modifier than for MeCN as modifier.…”

Section: Possible Separation Mechanisms On Macrocyclic Glycopeptide Cspsmentioning

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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“…Ráadásul egy királis molekula retenciója nemkirális és királis kölcsönhatások eredménye, melyek aránya jelentősen változhat a kromatográfiás körülményekkel [60][61][62][63][64][65] …”

Section: Királis Elválasztások Hőmérsékletfüggésének Rövid Irodalmi áunclassified

Poliszacharid és ciklofruktán típusú királis állófázisok alkalmazása enantiomerek elválasztására

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Study of mechanisms of chiral discrimination of amino acids and their derivatives on a teicoplanin-based chiral stationary phase

Cited by 104 publications

References 55 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

Poliszacharid és ciklofruktán típusú királis állófázisok alkalmazása enantiomerek elválasztására

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Study of mechanisms of chiral discrimination of amino acids and their derivatives on a teicoplanin-based chiral stationary phase

Cited by 104 publications

References 55 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

Poliszacharid és ciklofruktán típusú királis állófázisok alkalmazása enantiomerek elválasztására

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

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