Do we know the mechanism of chiral recognition between cyclodextrins and analytes?
The resolution of chiral phenethylamine analogue compounds were studied in presence of single-isomer neutral and negatively charged cyclodextrins (CDs) by means of capillary electrophoresis (CE) and NMR spectroscopy. Whereas the native β-CD and heptakis(2- N,N-dimethylcarbamoyl)β-cyclodextrin were n...
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| Veröffentlicht in: | Journal of pharmaceutical and biomedical analysis 2002-01, Vol.27 (3), p.531-540 |
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| container_title | Journal of pharmaceutical and biomedical analysis |
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| creator | Wedig, M. Laug, S. Christians, T. Thunhorst, M. Holzgrabe, U. |
| description | The resolution of chiral phenethylamine analogue compounds were studied in presence of single-isomer neutral and negatively charged cyclodextrins (CDs) by means of capillary electrophoresis (CE) and NMR spectroscopy. Whereas the native β-CD and
heptakis(2-
N,N-dimethylcarbamoyl)β-cyclodextrin were not able to separate the racemates of four ephedrine derivatives studied,
heptakis(2,3-
O-diacetyl)β-cyclodextrin and especially
heptakis(2,3-
O-diacetyl-6-sulfo)β-cyclodextrin could resolve all four pairs of enantiomers in one run. UV and NMR spectroscopic measurements revealed various kinds of complexes of phenethylamines with the CDs. Either defined inclusion complexes or manifold complexes which are mostly characterized by an attachment of the analyte to the outside of the CD cavity were found. No correlation between the kind of complexation and the resolution observed by means of CE could be found. |
| doi_str_mv | 10.1016/S0731-7085(01)00579-9 |
| format | Article |
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heptakis(2-
N,N-dimethylcarbamoyl)β-cyclodextrin were not able to separate the racemates of four ephedrine derivatives studied,
heptakis(2,3-
O-diacetyl)β-cyclodextrin and especially
heptakis(2,3-
O-diacetyl-6-sulfo)β-cyclodextrin could resolve all four pairs of enantiomers in one run. UV and NMR spectroscopic measurements revealed various kinds of complexes of phenethylamines with the CDs. Either defined inclusion complexes or manifold complexes which are mostly characterized by an attachment of the analyte to the outside of the CD cavity were found. No correlation between the kind of complexation and the resolution observed by means of CE could be found.</description><identifier>ISSN: 0731-7085</identifier><identifier>EISSN: 1873-264X</identifier><identifier>DOI: 10.1016/S0731-7085(01)00579-9</identifier><identifier>PMID: 11755754</identifier><language>eng</language><publisher>England: Elsevier B.V</publisher><subject>Capillary electrophoresis ; Chiral recognition ; Cyclodextrins ; Cyclodextrins - analysis ; Cyclodextrins - chemistry ; Electrophoresis, Capillary - methods ; Ephedrine derivatives ; Nuclear magnetic resonance ; Nuclear Magnetic Resonance, Biomolecular - methods ; Spectrophotometry, Ultraviolet ; Stereoisomerism</subject><ispartof>Journal of pharmaceutical and biomedical analysis, 2002-01, Vol.27 (3), p.531-540</ispartof><rights>2002 Elsevier Science B.V.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c361t-660859fe0173519d25840c21fc553aa249fbcc2e169518192b9b378e0bab95543</citedby><cites>FETCH-LOGICAL-c361t-660859fe0173519d25840c21fc553aa249fbcc2e169518192b9b378e0bab95543</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://dx.doi.org/10.1016/S0731-7085(01)00579-9$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,780,784,3548,27922,27923,45993</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/11755754$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Wedig, M.</creatorcontrib><creatorcontrib>Laug, S.</creatorcontrib><creatorcontrib>Christians, T.</creatorcontrib><creatorcontrib>Thunhorst, M.</creatorcontrib><creatorcontrib>Holzgrabe, U.</creatorcontrib><title>Do we know the mechanism of chiral recognition between cyclodextrins and analytes?</title><title>Journal of pharmaceutical and biomedical analysis</title><addtitle>J Pharm Biomed Anal</addtitle><description>The resolution of chiral phenethylamine analogue compounds were studied in presence of single-isomer neutral and negatively charged cyclodextrins (CDs) by means of capillary electrophoresis (CE) and NMR spectroscopy. Whereas the native β-CD and
heptakis(2-
N,N-dimethylcarbamoyl)β-cyclodextrin were not able to separate the racemates of four ephedrine derivatives studied,
heptakis(2,3-
O-diacetyl)β-cyclodextrin and especially
heptakis(2,3-
O-diacetyl-6-sulfo)β-cyclodextrin could resolve all four pairs of enantiomers in one run. UV and NMR spectroscopic measurements revealed various kinds of complexes of phenethylamines with the CDs. Either defined inclusion complexes or manifold complexes which are mostly characterized by an attachment of the analyte to the outside of the CD cavity were found. No correlation between the kind of complexation and the resolution observed by means of CE could be found.</description><subject>Capillary electrophoresis</subject><subject>Chiral recognition</subject><subject>Cyclodextrins</subject><subject>Cyclodextrins - analysis</subject><subject>Cyclodextrins - chemistry</subject><subject>Electrophoresis, Capillary - methods</subject><subject>Ephedrine derivatives</subject><subject>Nuclear magnetic resonance</subject><subject>Nuclear Magnetic Resonance, Biomolecular - methods</subject><subject>Spectrophotometry, Ultraviolet</subject><subject>Stereoisomerism</subject><issn>0731-7085</issn><issn>1873-264X</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2002</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqFkE1P3DAQhi0EggX6E0A-oXIIeJI4jk-o4ltCQiog9WY5zoQ1TWywsyz77-tlV_TIYTSXZz7eh5ADYCfAoDp9YKKATLCa_2RwzBgXMpMbZAK1KLK8Kv9skskXskN2Y3xhiQJZbpMdAMG54OWE_L7wdI70r_NzOk6RDmim2tk4UN9RM7VB9zSg8c_OjtY72uA4R3TULEzvW_wYg3WRatem0v1ixHi2T7Y63Uf8se575Onq8vH8Jru7v749_3WXmaKCMauq9JjskIEo0lttzuuSmRw6w3mhdV7KrjEmR6gkhxpk3simEDWyRjeS87LYI0erva_Bv80wjmqw0WDfa4d-FpWAImWXMoF8BZrgYwzYqddgBx0WCphaylSfMtXSlGKgPmWq5dzh-sCsGbD9P7W2l4CzFYAp5rvFoKKx6Ay2NjkbVevtNyf-AUl4g48</recordid><startdate>20020115</startdate><enddate>20020115</enddate><creator>Wedig, M.</creator><creator>Laug, S.</creator><creator>Christians, T.</creator><creator>Thunhorst, M.</creator><creator>Holzgrabe, U.</creator><general>Elsevier B.V</general><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>20020115</creationdate><title>Do we know the mechanism of chiral recognition between cyclodextrins and analytes?</title><author>Wedig, M. ; Laug, S. ; Christians, T. ; Thunhorst, M. ; Holzgrabe, U.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c361t-660859fe0173519d25840c21fc553aa249fbcc2e169518192b9b378e0bab95543</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2002</creationdate><topic>Capillary electrophoresis</topic><topic>Chiral recognition</topic><topic>Cyclodextrins</topic><topic>Cyclodextrins - analysis</topic><topic>Cyclodextrins - chemistry</topic><topic>Electrophoresis, Capillary - methods</topic><topic>Ephedrine derivatives</topic><topic>Nuclear magnetic resonance</topic><topic>Nuclear Magnetic Resonance, Biomolecular - methods</topic><topic>Spectrophotometry, Ultraviolet</topic><topic>Stereoisomerism</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Wedig, M.</creatorcontrib><creatorcontrib>Laug, S.</creatorcontrib><creatorcontrib>Christians, T.</creatorcontrib><creatorcontrib>Thunhorst, M.</creatorcontrib><creatorcontrib>Holzgrabe, U.</creatorcontrib><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 pharmaceutical and biomedical analysis</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Wedig, M.</au><au>Laug, S.</au><au>Christians, T.</au><au>Thunhorst, M.</au><au>Holzgrabe, U.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Do we know the mechanism of chiral recognition between cyclodextrins and analytes?</atitle><jtitle>Journal of pharmaceutical and biomedical analysis</jtitle><addtitle>J Pharm Biomed Anal</addtitle><date>2002-01-15</date><risdate>2002</risdate><volume>27</volume><issue>3</issue><spage>531</spage><epage>540</epage><pages>531-540</pages><issn>0731-7085</issn><eissn>1873-264X</eissn><abstract>The resolution of chiral phenethylamine analogue compounds were studied in presence of single-isomer neutral and negatively charged cyclodextrins (CDs) by means of capillary electrophoresis (CE) and NMR spectroscopy. Whereas the native β-CD and
heptakis(2-
N,N-dimethylcarbamoyl)β-cyclodextrin were not able to separate the racemates of four ephedrine derivatives studied,
heptakis(2,3-
O-diacetyl)β-cyclodextrin and especially
heptakis(2,3-
O-diacetyl-6-sulfo)β-cyclodextrin could resolve all four pairs of enantiomers in one run. UV and NMR spectroscopic measurements revealed various kinds of complexes of phenethylamines with the CDs. Either defined inclusion complexes or manifold complexes which are mostly characterized by an attachment of the analyte to the outside of the CD cavity were found. No correlation between the kind of complexation and the resolution observed by means of CE could be found.</abstract><cop>England</cop><pub>Elsevier B.V</pub><pmid>11755754</pmid><doi>10.1016/S0731-7085(01)00579-9</doi><tpages>10</tpages></addata></record> |
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| ispartof | Journal of pharmaceutical and biomedical analysis, 2002-01, Vol.27 (3), p.531-540 |
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| language | eng |
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| source | MEDLINE; ScienceDirect Journals (5 years ago - present) |
| subjects | Capillary electrophoresis Chiral recognition Cyclodextrins Cyclodextrins - analysis Cyclodextrins - chemistry Electrophoresis, Capillary - methods Ephedrine derivatives Nuclear magnetic resonance Nuclear Magnetic Resonance, Biomolecular - methods Spectrophotometry, Ultraviolet Stereoisomerism |
| title | Do we know the mechanism of chiral recognition between cyclodextrins and analytes? |
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