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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

  • Czech description

Classification

  • Type

    J<sub>x</sub> - Unclassified - Peer-reviewed scientific article (Jimp, Jsc and Jost)

  • CEP classification

    CC - Organic chemistry

  • OECD FORD branch

Result continuities

  • Project

  • 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

  • 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