2010
DOI: 10.1002/jssc.200900732
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Chiral capillary electrophoresis with cationic pyrrolidinium‐β‐cyclodextrin derivatives as chiral selectors

Abstract: New single-isomer, cationic beta-cyclodextrins, including mono-6-deoxy-6-pyrrolidine-beta-cyclodextrin chloride (pyCDCl), mono-6-deoxy-6-(N-methyl-pyrrolidine)-beta-cyclodextrin chloride (N-CH(3)-pyCDCl), mono-6-deoxy-6-(N-(2-hydroxyethyl)-pyrrolidine)-beta-cyclodextrin chloride (N-EtOH-pyCDCl), mono-6-deoxy-6-(2-hydroxymethyl-pyrrolidine)-beta-cyclodextrin chloride (2-MeOH-pyCDCl) were synthesized and used as chiral selectors in capillary electrophoresis for the enantioseparation of carboxylic and hydroxycarb… Show more

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Cited by 38 publications
(18 citation statements)
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References 65 publications
(74 reference statements)
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“…On the other hand, various types of cationic CDs have been synthesized and applied to the CDEKC analysis of amino acid racemates [44][45][46][47][48][49][50][51][52][53][54][55][56][57][58][59][60][61][62]. In contrast to anionic CDs, BGSs with pH 5-8,which is effective for separating neutral amino acids, are applied to EKC using cationic CDs (Table 2).…”
Section: Cdekcmentioning
confidence: 99%
See 1 more Smart Citation
“…On the other hand, various types of cationic CDs have been synthesized and applied to the CDEKC analysis of amino acid racemates [44][45][46][47][48][49][50][51][52][53][54][55][56][57][58][59][60][61][62]. In contrast to anionic CDs, BGSs with pH 5-8,which is effective for separating neutral amino acids, are applied to EKC using cationic CDs (Table 2).…”
Section: Cdekcmentioning
confidence: 99%
“…When the charged CDs interact with racemic amino acids, the analytes migrate at a different velocity from a surrounding aqueous phase due to the electrophoretic migration of the ionic CDs. Although various anionic [34][35][36][37][38][39][40][41][42][43] and cationic CDs [44][45][46][47][48][49][50][51][52][53][54][55][56][57][58][59][60][61][62] are synthesized for CDEKC as summarized in Table 2, sulfated CDs (S-CDs) [34,35] and highly sulfated CDs (HS-CDs) [36][37][38][39][40][41] are still the predominant CSs due to their resolution powers and commercial-availability. Since commercially available S-CDs and HS-CDs from Beckmann Coulter are not single isomers but a mixture of sulfated CDs with a different degree of substitution (average; 9 and 12, respectively), a wide range of OTG, 1-S-octyl-␤-d-thioglucopyranoside; DTDP, 3-(4,6-dichloro-1,3,5-triazinylamino)-7-dimethyamino-2-methylphenazine; LED-IF, light-emitting diode-induced fluorescence.…”
Section: Cdekcmentioning
confidence: 99%
“…Considering the existence of three types of hydroxyl groups located on the CD rims, the structurally simplest cationic CDs, mono-6 or 2-amino-CDs, were easily prepared with triphenylphosphine-catalyzed reduction of azido-CDs and a further hydrolysis [22]. Starting from mono-tosylated CDs, the nucleophilic attack by alkylimidazole [23], alkylamine [24] and alkylpyrrodine [25] can afford different series of mono-substituted cationic CDs.…”
Section: Monocationic and Dual-cationic Cds As Chiral Additivesmentioning
confidence: 99%
“…Optimum separation conditions were achieved at a CD concentration of 10 mM. A series of single isomer quaternary pyrrolidinium-β-CD derivatives were synthesized by Xiao and colleagues [61] including mono-6-deoxy-6-pyrrolidinium-β-CD, mono-6-deoxy-6-(N-methyl-pyrrolidinium)-β-CD, mono-6-deoxy-6-(N-(2-hydroxyethyl)-pyrrolidinium)-β-CD and mono-6-deoxy-6-(2-hydroxymethylpyrrolidinium)-β-CD. The highest resolution was achieved for dansyl-amino acids and carboxylic and hydroxycarboxylic acids using mono-6-deoxy-6-pyrrolidinium-β-CD as chiral selector in the pH range 6.0-9.0.…”
Section: New Chiral Selectors and Mechanistic Modelsmentioning
confidence: 99%