Comparative evaluation of the chiral recognition potential of single-isomer sulfated beta-cyclodextrin synthesis intermediates in non-aqueous capillary electrophoresis
The result's identifiers
Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F00216208%3A11310%2F16%3A10336411" target="_blank" >RIV/00216208:11310/16:10336411 - isvavai.cz</a>
Result on the web
<a href="http://dx.doi.org/10.1016/j.chroma.2016.07.033" target="_blank" >http://dx.doi.org/10.1016/j.chroma.2016.07.033</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.1016/j.chroma.2016.07.033" target="_blank" >10.1016/j.chroma.2016.07.033</a>
Alternative languages
Result language
angličtina
Original language name
Comparative evaluation of the chiral recognition potential of single-isomer sulfated beta-cyclodextrin synthesis intermediates in non-aqueous capillary electrophoresis
Original language description
The enantioselectivity of neutral single-isomer synthetic precursors of sulfated-beta-cyclodextrins was studied. Four neutral single-isomer cyclodextrins substituted on the secondary side with acetyl and/or methyl functional groups, heptakis(2-O-methyl-3,6-dihydroxy)-beta-cyclodextrin (HM-beta-CD), heptakis(2,3-di-O-acetyl-6-hydroxy)-beta-cyclodextrin (HDA-beta-CD), heptakis(2,3-di-O-methyl-6-hydroxy)-beta-cyclodextrin (HDM-beta-CD), heptakis(2-O-methyl-3-O-acetyl-6-hydroxy)-beta-cyclodextrin (HMA-beta-CD), and their sulfated analogs the negatively charged heptakis(2,3-di-O-methyl-6-sulfato)-beta-cyclodextrin (HDMS-beta-CD) and heptakis(2,3-di-O-acetyl-6-sulfato)-beta-cyclodextrin (HDAS-beta-CD) were investigated by non-aqueous capillary electrophoresis in the view of enantiodiscrimination for various drugs and related pharmaceutical compounds. The focus of the present work was on the chiral selectivity studies of the neutral derivatives, which are the synthesis intermediates of the sulfated products. The chiral recognition experiments proved that among the neutral compounds the HMA-beta-CD shows remarkable enantioselectivity towards chiral guests in non-aqueous capillary electrophoresis, while HM-beta-CD, HDA-beta-CD and HDM-beta-CD failed to resolve any of the 25 studied racemates under the applied experimental conditions. In order to get deeper insight into the molecular interactions between the studied single-isomer cyclodextrin and chiral fluoroquinolones (ofloxacin, gatifloxacin and lomefloxacin) and beta-blockers (propranolol), H-1 and ROESY NMR experiments were performed. The 2-O-methylation in combination with the 3-O-acetylation of the host was evidenced to exclusively carry the essential spatial arrangement for chiral recognition.
Czech name
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Czech description
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Classification
Type
J<sub>x</sub> - Unclassified - Peer-reviewed scientific article (Jimp, Jsc and Jost)
CEP classification
CC - Organic chemistry
OECD FORD branch
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Result continuities
Project
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Continuities
I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace
Others
Publication year
2016
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů
Data specific for result type
Name of the periodical
Journal of Chromatography A
ISSN
0021-9673
e-ISSN
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Volume of the periodical
1467
Issue of the periodical within the volume
October
Country of publishing house
NL - THE KINGDOM OF THE NETHERLANDS
Number of pages
9
Pages from-to
454-462
UT code for WoS article
000385323800044
EID of the result in the Scopus database
2-s2.0-84979518936