Enantiomeric and diastereomeric high-performance liquid chromatographic separation of cyclic β-substituted α-amino acids on a teicoplanin chiral stationary phase

Schlauch, Michael; Frahm, A. W.

doi:10.1016/s0021-9673(99)01222-4

Cited by 33 publications

(20 citation statements)

References 26 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%

“…Other possible solutions to separate two enantiomers include using chiral ligand-exchange chromatography [34] or a chiral stationary phase based on α-cyclodextrin [35], crown ether [36] or teicoplanin [37,38]. The detector most frequently used to analyse underivatised amino acids is the amperometric/electrochemical detector [39], which has low specificity.…”

Section: Introductionmentioning

confidence: 99%

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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%

Section: Introductionmentioning

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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“…92,93 As CSPs de teicoplanina e de teicoplanina aglicona são as mais utilizadas, principalmente para a resolução de aminoácidos quirais. [94][95][96][97][98] Porém, as CSPs de vancomicina e ristocetina também são úteis para a separação destes compostos. 89,99 Ademais, essas fases quirais apresentam enantiosseletividade para uma grande variedade de classes de compostos, tais como lactonas, 89 sulfóxidos 100 e alcaloides, 101 e fazem parte do protocolo de separação de produtos racêmicos de corporações farmacêuticas.…”

Section: Figura 4 Fases Quirais Derivadas De Fenilcarbamatos De Celuunclassified

Fases estacionárias quirais para cromatografia líquida de alta eficiência

2010

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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%

“…Other examples of the reverse elution sequence have been published for a-amino acids on ristocetin A in RP mode [82], for b-amino acids in POM [85] and also for b-amino acids on T-A 2-2 and teicoplanin aglycone in both RP mode and POM [86]. Schlauch et al [66] similarly observed the reverse elution sequence for cis-and trans-1-amino-2-hydroxycyclohexanecarboxylic acids on T-A2-2 , as did Xiao et al [96] for Dns-a-amino acids on ristocetin A and Chen [97] for N-benzoylisothiocyanated-a-amino acids on T-A 2-2 . Since some amino acids show the opposite elution sequence from that expected, it is not yet possible to predict the absolute configuration of an amino acid via its retention behavior on a macrocyclic glycopeptide CSP.…”

Section: Elution Sequence and Absolute Configuration Of Amino Acidsmentioning

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

159

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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Enantiomeric and diastereomeric high-performance liquid chromatographic separation of cyclic β-substituted α-amino acids on a teicoplanin chiral stationary phase

Cited by 33 publications

References 26 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

Fases estacionárias quirais para cromatografia líquida de alta eficiência

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

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