Document Detail

Synthesis of heptakis(2-O-methyl-3-O-acetyl-6-O-sulfo)-cyclomaltoheptaose, a single-isomer, sulfated beta-cyclodextrin carrying nonidentical substituents at all the C2, C3, and C6 positions and its use for the capillary electrophoretic separation of enantiomers in acidic aqueous and methanolic background electrolytes.
MedLine Citation:
PMID:  15818578     Owner:  NLM     Status:  MEDLINE    
The sodium salt of heptakis(2-O-methyl-3-O-acetyl-6-O-sulfo)cyclomaltoheptaose (HMAS), the first single-isomer, sulfated beta-cyclodextrin carrying nonidentical substituents at all of the C2, C3, and C6 positions, has been synthesized, analytically characterized, and used for the capillary electrophoretic separation of the enantiomers of a group of 24 weak base pharmaceuticals in acidic aqueous and acidic methanolic background electrolytes. HMAS interacted more strongly with most of the analytes studied than heptakis(2,3-di-O-methyl-6-O-sulfo)cyclomaltoheptaose, but less strongly than heptakis(2,3-di-O-acetyl-6-O-sulfo)cyclomaltoheptaose, the respective analogs with identical substituents at the C2 and C3 positions. The good separation selectivities and favorable normalized electroosmotic flow mobilities allowed for rapid, efficient separation of the enantiomers of 19 of the 24 weak base analytes in the aqueous and methanolic background electrolytes. The trends in the effective mobilities and separation selectivities as a function of the HMAS concentration closely followed the predictions of the ionic strength-corrected charged resolving agent migration model.
M Brent Busby; Gyula Vigh
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Publication Detail:
Type:  Journal Article; Research Support, Non-U.S. Gov't    
Journal Detail:
Title:  Electrophoresis     Volume:  26     ISSN:  0173-0835     ISO Abbreviation:  Electrophoresis     Publication Date:  2005 May 
Date Detail:
Created Date:  2005-05-10     Completed Date:  2005-12-23     Revised Date:  2006-11-15    
Medline Journal Info:
Nlm Unique ID:  8204476     Medline TA:  Electrophoresis     Country:  Germany    
Other Details:
Languages:  eng     Pagination:  1978-87     Citation Subset:  IM    
Department of Chemistry, Texas A&M University, College Station, TX 778742-3012, USA.
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MeSH Terms
Electrolytes / chemistry*
Electrophoresis, Capillary / methods*
Methanol / chemistry*
Water / chemistry*
beta-Cyclodextrins / chemical synthesis*,  chemistry*
Reg. No./Substance:
0/Electrolytes; 0/beta-Cyclodextrins; 0/heptakis(2-O-methyl-3-O-acetyl-6-O-sulfo)cyclomaltoheptaose; 67-56-1/Methanol; 7585-39-9/betadex; 7732-18-5/Water

From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine

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