Chiral separation of highly negatively charged enantiomers by capillary electrophoresis
The separation of two highly negatively charged enantiomeric organic disulfates containing two chiral centers was investigated by capillary electrophoresis using cyclodextrin based chiral selectors added to the run buffer. The optimum separation for the enantiomers was achieved in less than 3 min at...
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| Veröffentlicht in: | Journal of Chromatography A 2004-04, Vol.1033 (2), p.349-356 |
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| container_title | Journal of Chromatography A |
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| creator | Liu, Qinfeng Inoue, Takayo Kirchhoff, Jon R. Huang, Chunli Tillekeratne, L.M.V. Olmstead, Kay Hudson, R.A. |
| description | The separation of two highly negatively charged enantiomeric organic disulfates containing two chiral centers was investigated by capillary electrophoresis using cyclodextrin based chiral selectors added to the run buffer. The optimum separation for the enantiomers was achieved in less than 3
min at 25
°C with a run buffer of 10
mM glycine pH 2.4 and 5
mM QA-β-CD, which is a positively charged quaternary ammonium β-cyclodextrin derivative. The method resulted in baseline resolution, excellent linearity, and highly reproducible migration times allowing facile evaluation of the enantiomeric purity of the individual isomers. Detection limits for the enantiomeric pair were determined to be 0.3
ng/μl (S/N=3). The nature of the selector–enantiomer interaction and a quantitative measurement of the apparent stability constants that governed chiral discrimination of the enantiomers with QA-β-CD were also investigated by UV-Vis spectroscopy and electrospray ionization mass spectrometry. |
| doi_str_mv | 10.1016/j.chroma.2004.01.023 |
| format | Article |
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min at 25
°C with a run buffer of 10
mM glycine pH 2.4 and 5
mM QA-β-CD, which is a positively charged quaternary ammonium β-cyclodextrin derivative. The method resulted in baseline resolution, excellent linearity, and highly reproducible migration times allowing facile evaluation of the enantiomeric purity of the individual isomers. Detection limits for the enantiomeric pair were determined to be 0.3
ng/μl (S/N=3). The nature of the selector–enantiomer interaction and a quantitative measurement of the apparent stability constants that governed chiral discrimination of the enantiomers with QA-β-CD were also investigated by UV-Vis spectroscopy and electrospray ionization mass spectrometry.</description><identifier>ISSN: 0021-9673</identifier><identifier>DOI: 10.1016/j.chroma.2004.01.023</identifier><identifier>PMID: 15088757</identifier><identifier>CODEN: JOCRAM</identifier><language>eng</language><publisher>Amsterdam: Elsevier B.V</publisher><subject>Analytical chemistry ; Chemistry ; Chromatographic methods and physical methods associated with chromatography ; Chromatography, High Pressure Liquid ; Cyclodextrins ; Electrophoresis, Capillary - methods ; Enantiomer separation ; Exact sciences and technology ; Organosulfur compounds ; Other chromatographic methods ; Reproducibility of Results ; Sensitivity and Specificity ; Spectrophotometry, Ultraviolet ; Stability constants ; Stereoisomerism</subject><ispartof>Journal of Chromatography A, 2004-04, Vol.1033 (2), p.349-356</ispartof><rights>2004 Elsevier B.V.</rights><rights>2004 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c388t-8e20f90708f658259337fe976d488dd5d178471e6ed439719619fa52c39a446c3</citedby><cites>FETCH-LOGICAL-c388t-8e20f90708f658259337fe976d488dd5d178471e6ed439719619fa52c39a446c3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://dx.doi.org/10.1016/j.chroma.2004.01.023$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,780,784,3550,27924,27925,45995</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=15569252$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/15088757$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Liu, Qinfeng</creatorcontrib><creatorcontrib>Inoue, Takayo</creatorcontrib><creatorcontrib>Kirchhoff, Jon R.</creatorcontrib><creatorcontrib>Huang, Chunli</creatorcontrib><creatorcontrib>Tillekeratne, L.M.V.</creatorcontrib><creatorcontrib>Olmstead, Kay</creatorcontrib><creatorcontrib>Hudson, R.A.</creatorcontrib><title>Chiral separation of highly negatively charged enantiomers by capillary electrophoresis</title><title>Journal of Chromatography A</title><addtitle>J Chromatogr A</addtitle><description>The separation of two highly negatively charged enantiomeric organic disulfates containing two chiral centers was investigated by capillary electrophoresis using cyclodextrin based chiral selectors added to the run buffer. The optimum separation for the enantiomers was achieved in less than 3
min at 25
°C with a run buffer of 10
mM glycine pH 2.4 and 5
mM QA-β-CD, which is a positively charged quaternary ammonium β-cyclodextrin derivative. The method resulted in baseline resolution, excellent linearity, and highly reproducible migration times allowing facile evaluation of the enantiomeric purity of the individual isomers. Detection limits for the enantiomeric pair were determined to be 0.3
ng/μl (S/N=3). The nature of the selector–enantiomer interaction and a quantitative measurement of the apparent stability constants that governed chiral discrimination of the enantiomers with QA-β-CD were also investigated by UV-Vis spectroscopy and electrospray ionization mass spectrometry.</description><subject>Analytical chemistry</subject><subject>Chemistry</subject><subject>Chromatographic methods and physical methods associated with chromatography</subject><subject>Chromatography, High Pressure Liquid</subject><subject>Cyclodextrins</subject><subject>Electrophoresis, Capillary - methods</subject><subject>Enantiomer separation</subject><subject>Exact sciences and technology</subject><subject>Organosulfur compounds</subject><subject>Other chromatographic methods</subject><subject>Reproducibility of Results</subject><subject>Sensitivity and Specificity</subject><subject>Spectrophotometry, Ultraviolet</subject><subject>Stability constants</subject><subject>Stereoisomerism</subject><issn>0021-9673</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2004</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNp9kE1LxDAQhnNQ_P4HIr3obeskbfNxEWTxCwQviscQk-k2S9vUZFfw35tlF_TkaYbhmZeXh5BzCiUFyq-Xpe1iGEzJAOoSaAms2iNHAIzOFBfVITlOaQlABQh2QA5pA1KKRhyR93nno-mLhJOJZuXDWIS26Pyi67-LERf59IV5tZ2JC3QFjmbM1IAxFR_5bCbf9yZ-F9ijXcUwdSFi8umU7LemT3i2myfk7f7udf44e355eJrfPs9sJeVqJpFBq0CAbHkjWaOqSrSoBHe1lM41jgpZC4ocXV0pQRWnqjUNs5Uydc1tdUKutrlTDJ9rTCs9-GQxdxoxrJMWVOZIrjJYb0EbQ0oRWz1FP-TmmoLeSNRLvZWoNxI1UJ0l5reLXf76Y0D3-7QzmIHLHWCSNX0bzWh9-sM1XLGGZe5my2G28eUx6mQ9jhadj9mcdsH_3-QHo-iUOA</recordid><startdate>20040416</startdate><enddate>20040416</enddate><creator>Liu, Qinfeng</creator><creator>Inoue, Takayo</creator><creator>Kirchhoff, Jon R.</creator><creator>Huang, Chunli</creator><creator>Tillekeratne, L.M.V.</creator><creator>Olmstead, Kay</creator><creator>Hudson, R.A.</creator><general>Elsevier B.V</general><general>Elsevier</general><scope>IQODW</scope><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope></search><sort><creationdate>20040416</creationdate><title>Chiral separation of highly negatively charged enantiomers by capillary electrophoresis</title><author>Liu, Qinfeng ; Inoue, Takayo ; Kirchhoff, Jon R. ; Huang, Chunli ; Tillekeratne, L.M.V. ; Olmstead, Kay ; Hudson, R.A.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c388t-8e20f90708f658259337fe976d488dd5d178471e6ed439719619fa52c39a446c3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2004</creationdate><topic>Analytical chemistry</topic><topic>Chemistry</topic><topic>Chromatographic methods and physical methods associated with chromatography</topic><topic>Chromatography, High Pressure Liquid</topic><topic>Cyclodextrins</topic><topic>Electrophoresis, Capillary - methods</topic><topic>Enantiomer separation</topic><topic>Exact sciences and technology</topic><topic>Organosulfur compounds</topic><topic>Other chromatographic methods</topic><topic>Reproducibility of Results</topic><topic>Sensitivity and Specificity</topic><topic>Spectrophotometry, Ultraviolet</topic><topic>Stability constants</topic><topic>Stereoisomerism</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Liu, Qinfeng</creatorcontrib><creatorcontrib>Inoue, Takayo</creatorcontrib><creatorcontrib>Kirchhoff, Jon R.</creatorcontrib><creatorcontrib>Huang, Chunli</creatorcontrib><creatorcontrib>Tillekeratne, L.M.V.</creatorcontrib><creatorcontrib>Olmstead, Kay</creatorcontrib><creatorcontrib>Hudson, R.A.</creatorcontrib><collection>Pascal-Francis</collection><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Journal of Chromatography A</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Liu, Qinfeng</au><au>Inoue, Takayo</au><au>Kirchhoff, Jon R.</au><au>Huang, Chunli</au><au>Tillekeratne, L.M.V.</au><au>Olmstead, Kay</au><au>Hudson, R.A.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Chiral separation of highly negatively charged enantiomers by capillary electrophoresis</atitle><jtitle>Journal of Chromatography A</jtitle><addtitle>J Chromatogr A</addtitle><date>2004-04-16</date><risdate>2004</risdate><volume>1033</volume><issue>2</issue><spage>349</spage><epage>356</epage><pages>349-356</pages><issn>0021-9673</issn><coden>JOCRAM</coden><abstract>The separation of two highly negatively charged enantiomeric organic disulfates containing two chiral centers was investigated by capillary electrophoresis using cyclodextrin based chiral selectors added to the run buffer. The optimum separation for the enantiomers was achieved in less than 3
min at 25
°C with a run buffer of 10
mM glycine pH 2.4 and 5
mM QA-β-CD, which is a positively charged quaternary ammonium β-cyclodextrin derivative. The method resulted in baseline resolution, excellent linearity, and highly reproducible migration times allowing facile evaluation of the enantiomeric purity of the individual isomers. Detection limits for the enantiomeric pair were determined to be 0.3
ng/μl (S/N=3). The nature of the selector–enantiomer interaction and a quantitative measurement of the apparent stability constants that governed chiral discrimination of the enantiomers with QA-β-CD were also investigated by UV-Vis spectroscopy and electrospray ionization mass spectrometry.</abstract><cop>Amsterdam</cop><pub>Elsevier B.V</pub><pmid>15088757</pmid><doi>10.1016/j.chroma.2004.01.023</doi><tpages>8</tpages></addata></record> |
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| subjects | Analytical chemistry Chemistry Chromatographic methods and physical methods associated with chromatography Chromatography, High Pressure Liquid Cyclodextrins Electrophoresis, Capillary - methods Enantiomer separation Exact sciences and technology Organosulfur compounds Other chromatographic methods Reproducibility of Results Sensitivity and Specificity Spectrophotometry, Ultraviolet Stability constants Stereoisomerism |
| title | Chiral separation of highly negatively charged enantiomers by capillary electrophoresis |
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