Highly enantioselective HPLC separations using the covalently bonded macrocyclic antibiotic, ristocetin A, chiral stationary phase

Ekborg-Ott, K. Helen; Liu, Youbang; Armstrong, Daniel W.

doi:10.1002/(sici)1520-636x(1998)10:5<434::aid-chir10>3.0.co;2-0

Cited by 168 publications

(84 citation statements)

References 28 publications

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“…Macrocyclic antibiotics have been shown to be very effective chiral selectors both for HPLC and CE. The glycopeptides vancomycin [131], teicoplanin [132], ristocetin A [133] and avoparcin [134] as well as the polypeptide thiostrepton [131] and the ansamycin rifamycin B [131] have been used for the preparation of chiral HPLC phases. A comprehensive review on the application of macrocyclic antibiotics as chiral selectors for both HPLC and CE was recently given by Ward and Fattis [135].…”

Section: Direct Methodsmentioning

confidence: 99%

“…Teicoplanin [132] was used for the separation of amino acids, dipeptides [140,141] and unusual aromatic balkyl amino acids [141]. Ristocetin A was shown to be applicable to a broad spectrum of compounds [133] using either normal-phase, polar organic or reversed-phase mode. Avoparcin, has recently been introduced as a chiral selector and was demonstrated to have chiral recognition properties complementary to the other macrocyclic antibiotics [134].…”

Section: Direct Methodsmentioning

confidence: 99%

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Chiral separation by chromatographic and electromigration techniques. A Review

Gübitz

Schmid

2001

Biopharm & Drug Disp

225

135

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This review gives a survey of different chiral separation principles and their use in high-performance liquid chromatography (HPLC), gas chromatography (GC), supercritical fluid chromatography (SFC), thin-layer chromatography (TLC), capillary electrophoresis (CE) and capillary electrochromatography (CEC) highlighting new developments and innovative techniques. The mechanisms of the different separation principles are briefly discussed and some selected applications are shown.

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Section: Direct Methodsmentioning

confidence: 99%

Section: Direct Methodsmentioning

confidence: 99%

Chiral separation by chromatographic and electromigration techniques. A Review

Gübitz

Schmid

2001

Biopharm & Drug Disp

225

135

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“…For N-protected amino acids, the most efficient enantioseparations on ristocetin A as selector were achieved when the N-acyl group exhibited an aromatic character, and the separations were performed in RP mode or POM [20]. NPM separation appeared to be less effective in the enantiorecognition of N-acylated amino acids.…”

Section: Enantioseparation Of N-protected Proteins and Unusual Amino mentioning

confidence: 99%

“…Ristocetin A has a molecular mass of 2066, and consists of an aglycone portion with four joined macrocyclic rings (one twelve-membered, one fourteen-membered, and two sixteen-membered rings), to which several sugars (including arabinose, glucose, mannose and rhamnose) are covalently bonded ( Fig. 3) [20,44]. The molecule contains 38 stereogenic centers, seven aromatic rings, six amide linkages, twenty-one hydroxy groups, two primary amino groups, and one methyl ester.…”

Section: Ristocetin Amentioning

confidence: 99%

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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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Evaluation of the macrocyclic antibiotic avoparcin as a new chiral selector for HPLC

et al. 1998

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Avoparcin is a macrocyclic glycopeptide antibiotic structurally related to vancomycin, teicoplanin, and ristocetin A. When attached to 5‐μm spherical silica gel, the avoparcin proved to be an effective chiral stationary phase (CSP) that could be used in the reversed‐phase, normal‐phase, and polar‐organic modes. The avoparcin CSP was complimentary to the other macrocyclic glycopeptide CSPs in that it could resolve some racemates that the others could not, and vice versa. Some important compounds resolved on the avoparcin CSP include verapamil, thyroxine, mephenytoin, and 2‐imidazolidone‐4‐carboxylic acid. The use of this CSP and the optimization of separations on it are discussed. Avoparcin appears to be a useful addition to this family of CSPs. Chirality 10:627–660, 1998. © 1998 Wiley‐Liss, Inc.

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Highly enantioselective HPLC separations using the covalently bonded macrocyclic antibiotic, ristocetin A, chiral stationary phase

Cited by 168 publications

References 28 publications

Chiral separation by chromatographic and electromigration techniques. A Review

Chiral separation by chromatographic and electromigration techniques. A Review

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

Evaluation of the macrocyclic antibiotic avoparcin as a new chiral selector for HPLC

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