Medizinische Universität Graz Austria/Österreich - Forschungsportal - Medical University of Graz
Gewählte Publikation:
Eder, K; Sinner, F; Mupa, M; Huber, CG; Buchmeiser, MR.
Evaluation of norbornene- beta-cyclodextrin-based monomers and oligomers as chiral selectors by means of nonaqueous capillary electrophoresis.
Electrophoresis. 2001; 22(1):109-116
Doi: 10.1002/1522-2683(200101)22:1<109::AID-ELPS109>3.0.CO;2-P
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- Co-Autor*innen der Med Uni Graz
- Sinner Frank Michael
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- Abstract:
- Norbornen-5-yl carboxylic acid and norbornen-5-ylmethylsilyl ether-based beta-cyclodextrins (beta-CDs) containing up to three norbornene ester and up to five norbornene silyl ether units have been prepared from beta-CD and norbornen-5-carboxylic chloride and norbornen-5-ylmethyldichlorosilane, respectively. Oligomers (n = 2-4) were prepared therefrom using ring-opening metathesis polymerization (ROMP). Monomeric and oligomeric substituted beta-CDs were evaluated as chiral selectors in nonaqueous capillary zone electrophoresis using 35 mM sodium bicarbonate in N-methylformamide (NMF) as background electrolyte. Both monomeric and oligomeric norbornene ester- and norbornene silyl ether-type selectors showed good enantioresolution for dansylated (DNS-) amino acids using concentrations of the chiral selector of up to 4% w/v. A significant improvement in resolution was observed upon the introduction of up to five norbornene silyl ether units into a beta-CD molecule, whereas higher degrees of substitution with norbornen-5-yl-carboxyl groups lead to a reduction in enantioresolution of DNS-amino acids. Thus, pentakis(norbornen-5-ylmethylhydroxysiloxyl)-beta-CD turned out to be superior to mono(norbornen-5-ylmethylhydroxysiloxyl)-beta-CD in terms of enantioresolution. Moreover, norbornene silyl ether-type selectors were found to be more efficient than norbornene ester-type selectors. Finally, oligomeric selectors were found to possess superior or at least comparable enantioselectivity in the separation of DNS-amino acids compared to the parent monomers. A maximum in enantioresolution was obtained with oligo(pentakis(norbornen-5-ylmethylhydroxysiloxyl)beta-CD).
- Find related publications in this database (using NLM MeSH Indexing)
- Carbohydrate Sequence -
- Cyclodextrins - analysis
- Electrophoresis, Capillary - methods
- Ethers -
- Molecular Sequence Data -
- Molecular Structure -
- Norbornanes - analysis
- beta-Cyclodextrins -
- Find related publications in this database (Keywords)
- nonaqueous capillary electrophoresis
- monomeric and oligomeric beta-cyclodextrins
- Dansyl amino acids