Two novel, single-isomer, sulfated cyclodextrins, the sodium salts of heptakis(2-
O-methyl-3-O-acetyl-6-O-sulfo)cyclomaltoheptaose (HMAS) and heptakis(2-O-methyl-
6-O-sulfo)cyclomaltoheptaose (HMS) were used as chiral resolving agents in both
aqueous and non-aqueous electrophoretic separation of a set of pharmaceutically active
weak base enantiomers. Enantiomers of twenty one of the twenty four weak bases were
baseline resolved in one or more of the background electrolytes (BGE’s) used.
An eight-step synthetic method was used to produce, on a large scale, the title
compounds in greater than 97% purity. The purity of the synthetic intermediates and the
final products were characterized by HPLC-ELSD and indirect UV-detection capillary
electrophoresis (CE), respectively. X-ray crystallography, MALDI-TOF mass
spectrometry and 1H as well as 13C NMR spectroscopy allowed for unambiguous
characterization of the structure of each intermediate and the final product.
| Identifer | oai:union.ndltd.org:tamu.edu/oai:repository.tamu.edu:1969.1/3737 |
| Date | 16 August 2006 |
| Creators | Busby, Michael Brent |
| Contributors | Vigh, Gyula |
| Publisher | Texas A&M University |
| Source Sets | Texas A and M University |
| Language | en_US |
| Detected Language | English |
| Type | Book, Thesis, Electronic Dissertation, text |
| Format | 5579837 bytes, electronic, application/pdf, born digital |
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