Effect of temperature on retention of enantiomers of β-methyl amino acids on a teicoplanin chiral stationary phase

Péter, Antal; Török, G.; Armstrong, Daniel W.; Tóth, Géza; Tourwé, Dirk

doi:10.1016/s0021-9673(98)00835-8

Cited by 130 publications

(48 citation statements)

References 47 publications

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“…CHIROBIOTIC TAG is one of the most appropriate columns to analyse amino acids with a hyphenated system HPLC-MS and without any previous derivatisation because it permits to separate optical isomers using volatile mobile phase with a high percentage of organic solvent, preserving the spray stability [38,47,48].…”

Section: Chromatographic Separationmentioning

confidence: 99%

d- and l-amino acids in Antarctic lakes: assessment of a very sensitive HPLC-MS method

et al. 2014

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Amino acids represent a fraction of organic matter in marine and freshwater ecosystems, and a source of carbon, nitrogen and energy. L-Amino acids are the most common enantiomers in nature because these chiral forms are used during the biosynthesis of proteins and peptide. To the contrary, the occurrence of D-amino acids is usually linked to the presence of bacteria. We investigated the distribution of L-and D-amino acids in the lacustrine environment of Terra Nova Bay, Antarctica, in order to define their natural composition in this area and to individuate a possible relationship with primary production. A simultaneous chromatographic separation of 40 L-and D-amino acids was performed using a chiral stationary phase based on teicoplainin aglycone (CHIROBIOTIC TAG). The chromatographic separation was coupled to two different mass spectrometers-an LTQ-Orbitrap XL (Thermo Fisher Scientific) and an API 4000 (ABSciex)-in order to investigate their quantitative performance. High-performance liquid chromatography coupled with mass spectrometry methods were evaluated through the estimation of their linear ranges, repeatability, accuracy and detection and quantification limits. The high-resolution mass spectrometer LTQ-Orbitrap XL presented detection limits between 0.4 and 7 μgL −1 , while the triple quadrupole mass spectrometer API 4000 achieved the best detection limits reported in the literature for the quantification of amino acids (between 4 and 200 ngL −1 ). The most sensitive method, HPLC-API 4000, was applied to lake water samples.

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Section: Chromatographic Separationmentioning

confidence: 99%

d- and l-amino acids in Antarctic lakes: assessment of a very sensitive HPLC-MS method

et al. 2014

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“…No or only partial separation was achieved for aMe-substituted unusual amino acids (with the exception of a-methyl-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid (a-MeTic-3) [70,72] and for alicyclic b-amino acids [70]. Nice separations were attained for the b-substituteda-amino acid diastereomers (four enantiomers) of bMePhe, b-MeTyr, b-MeTic-3 and b-MeTrp [71], for different b-alkyl or aryl-substituted Trp analogs [73] and for the enantioseparation of Ala, Phe [74] and secondary amino acid analogs [75]. N-t-Boc protection in most cases decreased the quality of resolution relative to that for the nonprotected amino acid analogs [74].…”

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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“…The HPLC measurements were carried out on a Waters HPLC system consisting of an M-600 low-pressure gradient pump, an M-996 photodiode-array detector, and a Millenium 32 Chromatography Manager data system; the alternative Waters Breeze system consisted of a 1525 binary pump, a 487 dual-channel absorbance detector, a 717 plus autosampler, and Breeze data manager software (both systems from Waters Chromatography, Milford, MA). Both chromatographic systems were equipped with Rheodyne Model 7125 injectors (Cotati, CA) with 20-ll loops.…”

Section: Apparatus and Chromatographymentioning

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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Effect of temperature on retention of enantiomers of β-methyl amino acids on a teicoplanin chiral stationary phase

Cited by 130 publications

References 47 publications

d- and l-amino acids in Antarctic lakes: assessment of a very sensitive HPLC-MS method

d- and l-amino acids in Antarctic lakes: assessment of a very sensitive HPLC-MS method

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

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

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Effect of temperature on retention of enantiomers of β-methyl amino acids on a teicoplanin chiral stationary phase

Cited by 130 publications

References 47 publications

d- and l-amino acids in Antarctic lakes: assessment of a very sensitive HPLC-MS method

d- and l-amino acids in Antarctic lakes: assessment of a very sensitive HPLC-MS method

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

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

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