Use of a Macrocyclic Antibiotic, Rifamycin B, and Indirect Detection for the Resolution of Racemic Amino Alcohols by CE

Armstrong, Daniel W.; Rundlett, Kumber.; Reid, George L.

doi:10.1021/ac00082a015

Cited by 234 publications

(140 citation statements)

References 39 publications

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“…The ansamycins are of historical significance in that they were the first chiral selectors used exclusively in CE prior to their use in HPLC [17]. Their physicochemical data are listed in Table 1.…”

Section: The Ansamycinsmentioning

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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Section: The Ansamycinsmentioning

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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“…Generally, rifamycin B is chosen to separate cationic compounds [12,26], while the glycopeptide antibiotics vancomycin, teicoplanin and ristocetin A are used for the separation of compounds containing an anionic moiety such as carboxylate, phosphate, sulphonate groups, etc. Approximately 500 racemic analytes have been electrophoretically resolved with glycopeptide antibiotics, including most N-blocked amino acids, numerous nonsteroidal antiinflammatory compounds, antineoplasics, lactic acids, herbicides, rodenticides and a variety of pharmaceutically important compounds [15,17,18,21,22,28].…”

Section: Applicationsmentioning

confidence: 99%

“…The solubility increases in the short alcohols and acetone. Rifamycin B and SV give stable yellow to orange solutions depending in part on pH and organic cosolvents [12,26]. Rifamycin B is a diacid with pK a s of approximately 2.8 and 6.7.…”

Section: Structure and Physico-chemical Propertiesmentioning

confidence: 99%

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Enantioseparation in CE using macrocyclic antibiotics as chiral selectors

Hui¹,

Caude²

1999

Analusis

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Micellar phaseA mixed micelle system is obtained by adding surfactants such as SDS (sodium dodecylsulfate) above its critical micelle concentration (CMC) to the run buffers containing antibiotics. To date, only the glycopeptide antibiotics have been used in conjunction with micelles. In the case of vancomycin, it is estimated that approximately 90 % of vancomycin is bound to the SDS micelle. Thus there are three pseudophases: the free vancomycin, the vancomycin-SDS mixed micelle and the bulk aqueous solution. The use of such mixed micelle systems allow the resolution a variety of hydrophobic, neutral analytes, e.g., pesticides and drugs [16]. The major separation mechanism is thought to be the partitioning of hydrophobic, neutral compounds between the three pseudophases. In a recent study, Rundlett and Armstrong [17] found the addition of SDS micelles with vancomycin to the run buffer can reverse the elution order of enantiomers, decreases analysis times and enhances efficiencies by one order of magnitude.The addition of SDS to a teicoplanin-based separation produces similar effects to vancomycin experiments [17,22]. However, the elution order of enantiomers in teicoplanin system is not universal. In the case of ristocetin A, the addition of SDS to the analogous conditions does not produce the extensive increase in efficiency and decrease in migration times. Furthermore, there is a significant concentrationdependent effect on selectivity and the reversal of elution order is uncommon [21]. Complementarity among glycopeptide antibiotics used as chiral selectorsAlthough all of three glycopeptide antibiotics vancomycin, teicoplanin and ristocetin A belong to the same family, they have some distinct structural differences as well. Therefore, they exhibit somewhat similar but not identical enantioselectivities. In fact, the glycopeptide antibiotics are complementary to one another. Armstrong et al. proposed that if only a partial enantioresolution can be obtained with one glycopeptide, there is a high probability that a baseline or better separation may be obtained with another glycopeptide [30]. This "principle of complementary separations" is illustrated in figure 3. While it is not yet possible to predict which glycopeptide antibiotic will provide the best resolution for a given analyte, it appears that a partial resolution with one selector usually can be improved upon by using one of the structurally related macrocyclic glycopeptide chiral selectors. ApplicationsGenerally, rifamycin B is chosen to separate cationic compounds [12,26], while the glycopeptide antibiotics vancomycin, teicoplanin and ristocetin A are used for the separation of compounds containing an anionic moiety such as carboxylate, phosphate, sulphonate groups, etc. Approximately 500 racemic analytes have been electrophoretically resolved with glycopeptide antibiotics, including most N-blocked amino acids, numerous nonsteroidal antiinflammatory compounds, antineoplasics, lactic acids, herbicides, rodenticides and a variety of pharmaceutically im...

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“…Used as chiral selectors for LC, TLC, GC, SFC, and CE, macrocyclic antibiotics compounds were first introduced by Armstrong et al [143][144][145]. This class of compound falls into two categories: ansamycin antibiotics (rifamycin B and SV) and the amphotiric 23 glycopeptide antibiotics (vancomycin, ristocetin A, and teicopianin).…”

Section: Antibioticsmentioning

confidence: 99%

Capillary electrophoresis separation of neutral organic compounds, pharmaceutical drugs, proteins and peptides, enantiomers and anions

Ding

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This manuscript has been reproduced from the microfilm master. UMI films the t»ct directly from the original or copy submitted. Thus, some thesis and dissertation copies are in typewriter face, while others may be from any type of computer printer.The quality of this reproduction is dependent upon the quality of the copy submitted. Broken or indistinct print, colored or poor quality illustrations and photographs, print bleedthrough, substandard margins, and improper alignment can adversely affect reproduction.In the unlikely event that the author did not send UMI a complete manuscript and there are missing pages, these will be noted. Also, if unauthorized copyright material had to be removed, a note will indicate the deletion.Oversize materials (e.g., maps, drawings, charts) are reproduced by sectioning the original, beginning at the upper left-hand comer and continuing from left to right in equal sections with small overlaps. Each original is also photographed in one e7q)osure and is included in reduced form at the back of the book.Photographs included in the original manuscript have been reproduced xerographically in this copy. Higher quality 6" x 9" black and white photographic prints are available for any photographs or illustrations appearing in this copy for an additional charge. Contact UMI directly to order. The effect of adding this new surfactant to the acidic electrolyte was also investigated. UMIWorking at acidic condition at pH 2.4 has the advantage that electroosmotic flow is virtually eliminated. Neutral compounds are dragged by their association with the surfactant, moving as the same direction as the surfactant, resulting in fast separations. Basic compounds are also investigated under the same conditions. Excellent resolution of a mixture of 19 polyaromatic hydrocarbons was obtained in only 20 min.Incorporation of cetyltrimethylammonium bromide in the electrolyte is shown to dynamically coat the capillary and reverse electroosmotic flow. The coating prevents basic proteins and peptides adsorption into the capillary wall, resulting in high separation efficiencies. A systematic study of experimental parameters demonstrated the importance of selecting a suitable buffer and an appropriate pH.Gliral recogmtion mechanism is smdied using several novel synthetic surfactants as chiral selectors, which are made from amino acids reacting with al&yl chloroformates. It was found that enantiomeric resolution can be readily manipulated by varying the alkyl groups (different chain lengths), amino acids and surfactant concentrations. Sulfonated Bcyclodextrin is also employed as a chiral selector to compare chiral selectivity with these synthetic surfactants. A duo-chiral selectors system is further investigated for the possibility of eliminating some tedious steps in chiral compounds method development.A satisfactory separation of both inorganic and organic anions is obtained using electrolyte solutions as high as 5 M sodium chloride using direct photometric detection. The temperature inside the capillary that ...

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Use of a Macrocyclic Antibiotic, Rifamycin B, and Indirect Detection for the Resolution of Racemic Amino Alcohols by CE

Cited by 234 publications

References 39 publications

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

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

Enantioseparation in CE using macrocyclic antibiotics as chiral selectors

Capillary electrophoresis separation of neutral organic compounds, pharmaceutical drugs, proteins and peptides, enantiomers and anions

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