Single-isomer carboxymethyl-gamma-cyclodextrin as chiral resolving agent for capillary electrophoresis

Result code in IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F00216208%3A11310%2F16%3A10336409" target="_blank" >RIV/00216208:11310/16:10336409 - isvavai.cz</a>

Result on the web

<a href="http://dx.doi.org/10.1016/j.chroma.2016.06.083" target="_blank" >http://dx.doi.org/10.1016/j.chroma.2016.06.083</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.1016/j.chroma.2016.06.083" target="_blank" >10.1016/j.chroma.2016.06.083</a>

Result language

angličtina

Original language name

Single-isomer carboxymethyl-gamma-cyclodextrin as chiral resolving agent for capillary electrophoresis

Original language description

Herein we report on the synthesis, characterization and the novel capillary electrophoretic use of octakis-(2,3-di-O-methyl-6-O-carboxymethyl)-gamma-cyclodextrin sodium salt (ODMCM). ODMCM is the first single-isomer carboxymethyl-gamma-cyclodextrin that is fully methylated on its secondary side and carries ionizable carboxymethyl functions on its primary side. ODMCM was prepared with high isomeric purity through a four-step synthetic procedure. The purity of each intermediate was characterized by appropriate chromatographic methods, while the isomeric purity of the carboxymethylated product was determined by an HPLC method using a CD-Screen-IEC column and by a capillary electrophoretic method using indirect UV detection, as well. The structural identification of the ODMCM was carried out by 1D, 2D NMR spectroscopy and ESI-MS. The acid-base characterization of the chiral selector was carried out by H-1 NMR-pH titration. The chiral separation ability of the synthesized selector was studied by chiral capillary electrophoresis. ODMCM was used as a background electrolyte additive to separate enantiomers of representative pharmacologically significant model molecules such as propranolol, citalopram, ketamine, tapentadol and dapoxetine. The effects of the selector concentration and the pH of the background electrolyte on the enantiorecognition properties were investigated. H-1 NMR spectroscopy was further applied to get deeper insight of the host-guest inclusion complex formation. The pH-dependent enantioselectivity of this new single-isomer chiral selector was demonstrated by chiral capillary electrophoresis and H-1 NMR spectroscopy.

Czech name

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Czech description

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Type

J_x - Unclassified - Peer-reviewed scientific article (Jimp, Jsc and Jost)

CEP classification

CC - Organic chemistry

OECD FORD branch

—

Project

—

Continuities

I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace

Publication year

2016

Confidentiality

S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

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

445-453

UT code for WoS article

000385323800043

EID of the result in the Scopus database

2-s2.0-84991083715