Evaluation of newly synthesized and commercially available charged cyclomaltooligosaccharides (cyclodextrins) for capillary electrokinetic chromatography

Mustafa Culha, Fred M. Schell, Shannon Fox, Thomas Green, Thomas Betts, Michael J. Sepaniak

Research output: Contribution to journalArticlepeer-review

2 Scopus citations


A highly new charged cyclodextrin (CD) derivatives, (6-O-carboxymethyl-2,3- di-O-methyl)cyclomaltoheptaoses (CDM-β-CDs), was synthesized and characterized as anionic reagents for capillary electrophoresis (CE) in an electrokinetic chromatography mode of separation. Substitution with dimethyl groups at the secondary hydroxyl sites of the CD is aimed at influencing the magnitude and selectivity of analyte-CD interactions, while substitution by carboxymethyl groups at the primary hydroxyl sites provides for high charge and electrophoretic mobility. Full regioselective methylation at the secondary hydroxyl sites was achieved in this work, while substitution at the primary hydroxyl sites generated a mixture of multiply charged products. The separation performance of CDM-β-CD was evaluated using a variety of analyte mixtures. The results obtained from commercially available negatively charged cyclodextrins, heptakis(2,3-di-O-methyl-6-O-sulfo)cyclomaltoheptaose (HDMS-β-CD) and O-(carboxymethyl)cyclomaltoheptaose (CM-β-CD) with an average degree of substitution one (DS 1), were compared to CDM-β-CD using a sample composed of eight positional isomers of dihydroxynaphthalene. Four hydroxylated polychlorobiphenyl derivatives, a group of chiral and isomeric catchecins, and chiral binaphthyl compounds were also separated with CDM-β-CD. The effect of adding neutral β-cyclodextrin (β-CD) into the running buffer containing charged cyclodextrins was investigated and provided evidence of significant inter-CD interactions. Under certain running buffer conditions, the charged cyclodextrins also appear to adsorb to the capillary walls to various degrees.

Original languageEnglish (US)
Pages (from-to)241-249
Number of pages9
JournalCarbohydrate Research
Issue number2
StatePublished - Jan 22 2004
Externally publishedYes


  • Capillary electrophoresis
  • Characterization
  • Chiral separations
  • Heptakis(6-O-carboxymethyl-2,3-di-O-methyl)cyclomaltoheptaose
  • Neutral positional isomers

ASJC Scopus subject areas

  • Analytical Chemistry
  • Biochemistry
  • Organic Chemistry


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