Immobilized vancomycin as chiral stationary phase in packed capillary liquid chromatography

Svensson, L.A.; Karlsson, K.; Vessman, Jörgen

doi:10.1002/(sici)1520-636x(1998)10:3<273::aid-chir10>3.0.co;2-x

Cited by 33 publications

(10 citation statements)

References 37 publications

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“…1), a macrocyclic antibiotic, is an amphoteric glycopeptide produced by Streptomyces orientalis which has proven to be a viable chiral selector for HPLC. [12][13][14][15][16][17] While it is related to other glycopeptide antibiotics, vancomycin has a number of unique structural features, including 18 stereogenic centers, five aromatic rings, and two side chains one of which is a carbohydrate dimer. Therefore, a vancomycin-based stationary phase appears to be multimodal in that it can be utilized in both normal-phase and reversed-phase liquid chromatography.…”

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confidence: 99%

Liquid chromatography/atmospheric pressure chemical ionization tandem mass spectrometry enantiomeric separation ofdl-threo-methylphenidate, (Ritalin®) using a macrocyclic antibiotic as the chiral selector

Ramos

Bakhtiar

Majumdar

et al. 1999

Rapid Commun. Mass Spectrom.

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Vancomycin, a macrocyclic antibiotic, is an amphoteric glycopeptide produced by Streptomyces orientalis which has proven to be a viable chiral selector for high performance liquid chromatograph (HPLC) (D. W. Armstrong, Y. Tang, S. Chen, Y. Zhou, C. Bagwill and J-R. Chen, Anal. Chem. (1994; 66: 1473). While it is related to other glycopeptide antibiotics, vancomycin has a number of unique structural features, including 18 stereogenic centers, five aromatic rings, and two side chains one of which is a carbohydrate dimer. Therefore, a vancomycin-based stationary phase appears to be multimodal in that it can be utilized in both normal-phase and reversed-phase liquid chromatography. Consequently, the enantiomeric separation may be operative via several mechanisms, including pi-pi complexation, dipole stacking, inclusion, hydrogen bonding, or combinations of these interactions. LC/MS/MS is a powerful tool for quantitative analysis when evaluated on the basis of speed, specificity, reliability and sensitivity. For these reasons, the present paper explored the feasibility of bonded macrocyclic glycopeptide phases for chiral LC/MS/MS quantitative analysis. Methylphenidate was used as a model compound. A rapid chiral bioanalytical method (<7.5 min) for the determination of the enantiomers of methylphenidate was developed. A lower limit of quantification (LLOQ) of 87 pg/mL was attained for the human plasma assay. This is to our knowledge the first example of enantioselective reversed-phase LC/MS/MS for methylphenidate. The chiral column was relatively cost effective and exhibited excellent performance with no separation deterioration observed after approximately 2500 injections.

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confidence: 99%

Liquid chromatography/atmospheric pressure chemical ionization tandem mass spectrometry enantiomeric separation ofdl-threo-methylphenidate, (Ritalin®) using a macrocyclic antibiotic as the chiral selector

Ramos

Bakhtiar

Majumdar

et al. 1999

Rapid Commun. Mass Spectrom.

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“…This maybe due to increased competition of salt for the interaction sites of the stationary phase (e.g. ionic interaction sites) [31, 32]. …”

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confidence: 99%

Enantioseparations of chiral ruthenium(II) polypyridyl complexes using HPLC with macrocyclic glycopeptide chiral stationary phases (CSPs)

Krishnan

Yadav

MacDonnell

et al. 2008

Journal of Molecular Structure

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A high performance liquid chromatographic method using macrocyclic glycopeptide chiral stationary phases (CSPs) was used to separate enantiomers of seven ruthenium(II) polypyridyl complexes. Among the five different CSPs, the Chirobiotic T2 was most effective and baseline separated all complexes. All complexes show the same elution order with the Δ-enantiomer being retained longer than the Λ-enantiomer. The mobile phase composition, including organic modifier type, organic modifier percent, salt type, and salt concentration, produced significant effects on the enantioresolution.

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“…Data from the literature indicate that chiral phases with engrafted macrocyclic antibiotics show promise in the separation of profens, which exhibit anti-inflammatory effects [12][13][14][15]. The therapeutic activity, however, resides in only one profen enantiomer, hence, the need for separation and determination of profens.…”

Section: Resultsmentioning

confidence: 99%

“…On the whole, the best results of RP-HPLC separation of indoprofen and ibuprofen were achieved with E-SiO 2 (the maximum values of α equaled 1.99 and 1.70), and those of ketoprofen and phenoprofen, respectively, with R-SiO 2 ( α 1.94) and EA-SiO 2 ( α 1.58) . Thus, the operational characteristics of our sorbents are superior to those of commercially available phases (such as Chirobiotic) [12][13][14][15]. The sorbent with immobilized vancomycin exhibited no selectivity for profens in the RP-HPLC setting; its appreciable selectivity under the conditions of PI-HPLC was limited to flurbiprofen, however.…”

Section: Resultsmentioning

confidence: 99%

Sorbents with immobilized glycopeptide antibiotics for separating optical isomers by high-performance liquid chromatography

Кузнецов

Nesterenko

Vasiyarov

et al. 2006

Appl Biochem Microbiol

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The increasing attention being paid by researchers to studies in the field of stereoselective synthesis and catalysis, as well as methods of chromatographic separation of chiral phases, observed over the last decade, is due to the requirements of the World Health Organization for the optical purity of drugs. The lack of universally applicable chiral phases for separating optical isomers prompts researchers to develop new sorbents. Immobilized macrocyclic glycopeptide antibiotics (including vancomycin, teichoplanin, ristocetin A, avoparcin, etc.) proved to serve as chiral phases for reliable HPLC separation of a wide range of drugs [1][2][3][4]. The high enantioselectivity of the sorbents belonging to this class is due to the presence of structurally diverse fragments capable of multiple-point interactions with the compounds to be separated (in both polar and nonpolar solvents). Immobilization of new antibiotics [5], chemical modifications of their structure [6], and refinement of immobilization techniques [7] offer additional possibilities for changing the enantioselectivity of sorbents belonging to this class.It was previously shown that eremomycin (a new antibiotic manufactured in Russia), in contrast to its closest structural analogue vancomycin, exhibits high enantioselectivity in separating isomers of α amino acids when immobilized on silica gel [8]. A method of its immobilization was developed that increased the selectivity of the separation, thus, rendering the sorbent superior to other chiral selectors in separating isomers of α amino acids [9].In this work, we sought to explore the capacity of the new eremomycin sorbent for separating enantiomers of other classes (profens) and study the effects of structural modification of eremomycin on its enantioselectivity, as compared to the known chiral selectors vancomycin and ristomycin. MATERIALS AND METHODSReagents. The antibiotics were immobilized using modified silica gels: Diaspher-110-Epoxy (particle size, 6 µ m; specific surface, 313 m 2 /g; pore diameter, 11 nm; carbon content, 5.2%) and Diasorb-130-Epoxy (particle size, 6 µ m; specific surface, 280 m 2 /g; pore diameter, 13 nm; carbon content, 4.8%) manufactured by BioChemMack ST Russia. The eluants were prepared using methanol, acetic acid, and triethylamine (Fluka, Switzerland). Eremomycin and ristomycin were synthesized using a pilot plant at the Hause Institute for New Antibiotics (Russia) [10,11]. Vancomycin was provided by the joint stock company Veropharm (Russia). The profens and amino acids were purchased from Sigma (United States).Obtaining eremosaminyl aglycon of eremomycin [4]. Eremomycin (3 g) was dissolved in 30 ml of dimethyl sulphoxide, and the solution was supplemented with 2 ml of 80% sulfuric acid, after which the mixture Kuznetsov a , P. N. Nesterenko a , G. G. Vasiyarov a , and S Abstract -Chiral sorbents for HPLC separation of optical isomers carrying glycopeptide antibiotics (eremomycin or its eremosaminyl aglycon, ristomycin, or vancomycin) fixed onto the surface of silica gel...

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Immobilized vancomycin as chiral stationary phase in packed capillary liquid chromatography

Cited by 33 publications

References 37 publications

Liquid chromatography/atmospheric pressure chemical ionization tandem mass spectrometry enantiomeric separation ofdl-threo-methylphenidate, (Ritalin®) using a macrocyclic antibiotic as the chiral selector

Liquid chromatography/atmospheric pressure chemical ionization tandem mass spectrometry enantiomeric separation ofdl-threo-methylphenidate, (Ritalin®) using a macrocyclic antibiotic as the chiral selector

Enantioseparations of chiral ruthenium(II) polypyridyl complexes using HPLC with macrocyclic glycopeptide chiral stationary phases (CSPs)

Sorbents with immobilized glycopeptide antibiotics for separating optical isomers by high-performance liquid chromatography

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