Click chemistry immobilization strategies in the development of strong cation exchanger chiral stationary phases for HPLC
Enantioseparation of chiral amines with HPLC has developed into a widely used analytical and preparative tool. Chiral basic molecules, which act as cationic species upon protonation, are suited for an enantioselective cation exchange process. Novel strong cation exchangers (SCX) based on different 3...
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| Veröffentlicht in: | Journal of separation science 2013-09, Vol.36 (17), p.2826-2837 |
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| container_title | Journal of separation science |
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| creator | Wolrab, Denise Frühauf, Peter Kohout, Michal Lindner, Wolfgang |
| description | Enantioseparation of chiral amines with HPLC has developed into a widely used analytical and preparative tool. Chiral basic molecules, which act as cationic species upon protonation, are suited for an enantioselective cation exchange process. Novel strong cation exchangers (SCX) based on different 3,5‐disubstituted benzoic acids functionalized with trans‐(R,R)‐ and trans‐(S,S)‐2‐aminocyclohexanesulfonic acid as the chiral selector (SO) and ion exchange unit were synthesized. Employing 1,3‐dipolar cycloaddition (azide–yne click chemistry), the SOs were immobilized onto azidopropyl‐modified silica gel. This immobilization strategy enables controlled loading of the SO, and especially, high SO density on the silica surface compared to the thiol–ene click immobilization. The performance of the novel SCX chiral stationary phases was evaluated under polar organic mode conditions with different ratios of methanol and acetonitrile, thereby changing the polarity of the bulk mobile phase. The type of co‐ and counterion additives employed in the mobile phase was varied as well. The influence of the formed 1,2,3‐triazol spacer as well as different substitution patterns in the benzene unit on the chiral recognition properties of the SOs is discussed. |
| doi_str_mv | 10.1002/jssc.201300559 |
| format | Article |
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Chiral basic molecules, which act as cationic species upon protonation, are suited for an enantioselective cation exchange process. Novel strong cation exchangers (SCX) based on different 3,5‐disubstituted benzoic acids functionalized with trans‐(R,R)‐ and trans‐(S,S)‐2‐aminocyclohexanesulfonic acid as the chiral selector (SO) and ion exchange unit were synthesized. Employing 1,3‐dipolar cycloaddition (azide–yne click chemistry), the SOs were immobilized onto azidopropyl‐modified silica gel. This immobilization strategy enables controlled loading of the SO, and especially, high SO density on the silica surface compared to the thiol–ene click immobilization. The performance of the novel SCX chiral stationary phases was evaluated under polar organic mode conditions with different ratios of methanol and acetonitrile, thereby changing the polarity of the bulk mobile phase. The type of co‐ and counterion additives employed in the mobile phase was varied as well. The influence of the formed 1,2,3‐triazol spacer as well as different substitution patterns in the benzene unit on the chiral recognition properties of the SOs is discussed.</description><identifier>ISSN: 1615-9306</identifier><identifier>EISSN: 1615-9314</identifier><identifier>DOI: 10.1002/jssc.201300559</identifier><identifier>PMID: 23801658</identifier><language>eng</language><publisher>Weinheim: Blackwell Publishing Ltd</publisher><subject>Aminoethanol-based drugs ; Analysis ; Analytical chemistry ; Biological and medical sciences ; Cation Exchange Resins ; Cation exchanging ; Chemical synthesis ; Chemistry ; Chiral cation exchange ; Chiral stationary phases ; Chromatographic methods and physical methods associated with chromatography ; Chromatography ; Chromatography, High Pressure Liquid - instrumentation ; Chromatography, Ion Exchange - instrumentation ; Copper-catalyzed reactions ; Cycloaddition ; Density ; Enantiomer separation ; Exact sciences and technology ; General pharmacology ; Immobilization ; Magnetic Resonance Spectroscopy ; Medical sciences ; Methyl alcohol ; Other chromatographic methods ; Pharmacology. Drug treatments ; Phases ; Spectrometry, Mass, Electrospray Ionization ; Strategy</subject><ispartof>Journal of separation science, 2013-09, Vol.36 (17), p.2826-2837</ispartof><rights>2013 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><rights>2014 INIST-CNRS</rights><rights>2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.</rights><rights>2013 WILEY-VCH Verlag GmbH & Co. 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Sep. Science</addtitle><description>Enantioseparation of chiral amines with HPLC has developed into a widely used analytical and preparative tool. Chiral basic molecules, which act as cationic species upon protonation, are suited for an enantioselective cation exchange process. Novel strong cation exchangers (SCX) based on different 3,5‐disubstituted benzoic acids functionalized with trans‐(R,R)‐ and trans‐(S,S)‐2‐aminocyclohexanesulfonic acid as the chiral selector (SO) and ion exchange unit were synthesized. Employing 1,3‐dipolar cycloaddition (azide–yne click chemistry), the SOs were immobilized onto azidopropyl‐modified silica gel. This immobilization strategy enables controlled loading of the SO, and especially, high SO density on the silica surface compared to the thiol–ene click immobilization. The performance of the novel SCX chiral stationary phases was evaluated under polar organic mode conditions with different ratios of methanol and acetonitrile, thereby changing the polarity of the bulk mobile phase. The type of co‐ and counterion additives employed in the mobile phase was varied as well. The influence of the formed 1,2,3‐triazol spacer as well as different substitution patterns in the benzene unit on the chiral recognition properties of the SOs is discussed.</description><subject>Aminoethanol-based drugs</subject><subject>Analysis</subject><subject>Analytical chemistry</subject><subject>Biological and medical sciences</subject><subject>Cation Exchange Resins</subject><subject>Cation exchanging</subject><subject>Chemical synthesis</subject><subject>Chemistry</subject><subject>Chiral cation exchange</subject><subject>Chiral stationary phases</subject><subject>Chromatographic methods and physical methods associated with chromatography</subject><subject>Chromatography</subject><subject>Chromatography, High Pressure Liquid - instrumentation</subject><subject>Chromatography, Ion Exchange - instrumentation</subject><subject>Copper-catalyzed reactions</subject><subject>Cycloaddition</subject><subject>Density</subject><subject>Enantiomer separation</subject><subject>Exact sciences and technology</subject><subject>General pharmacology</subject><subject>Immobilization</subject><subject>Magnetic Resonance Spectroscopy</subject><subject>Medical sciences</subject><subject>Methyl alcohol</subject><subject>Other chromatographic methods</subject><subject>Pharmacology. Drug treatments</subject><subject>Phases</subject><subject>Spectrometry, Mass, Electrospray Ionization</subject><subject>Strategy</subject><issn>1615-9306</issn><issn>1615-9314</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2013</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqNkk1v1DAQhiNERT_gyhFFQkhcsvgjduIjiqBLtS2IguBmOc5419sk3trZ0uXX45DtInGBi23NPPOOZl4nyXOMZhgh8mYdgp4RhClCjIlHyQnmmGWC4vzx4Y34cXIawhohXJQCPUmOCS0R5qw8SXZVa_VNqlfQ2TD4XWq7ztW2tT_VYF2fxpgaYGkhpLZPhxWkDdxB6zYd9EPqzAi4fpnqCYd7vVL9EnxUtF61Mf07oaLyZqVClDHOp_NPi-ppcmRUG-DZ_j5Lvr5_96WaZ4uP5x-qt4tMM8RxVhgAzCkiDNGaUdzEOYkwpqFYQ4kUaWpBjFIaG9IIanRNOdINL2g8OGB6lryedDfe3W4hDDJOqqFtVQ9uGyTO87LICybYf6AUlTknRET05V_o2m19HweJFBEFI6QoIzWbKO1dCB6M3HjbxWVIjOTonxz9kwf_YsGLvey27qA54A-GReDVHlBBq9Z41Wsb_nBF7Mz5yOUT98O2sPtHW3lxfV1RKsZlZVNZ_AxwfyhT_kbGjRZMfrs6l4v51Wf-XSB5SX8BkvzDig</recordid><startdate>201309</startdate><enddate>201309</enddate><creator>Wolrab, Denise</creator><creator>Frühauf, Peter</creator><creator>Kohout, Michal</creator><creator>Lindner, Wolfgang</creator><general>Blackwell Publishing Ltd</general><general>Wiley</general><general>Wiley Subscription Services, Inc</general><scope>BSCLL</scope><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>7U5</scope><scope>8FD</scope><scope>L7M</scope><scope>7X8</scope></search><sort><creationdate>201309</creationdate><title>Click chemistry immobilization strategies in the development of strong cation exchanger chiral stationary phases for HPLC</title><author>Wolrab, Denise ; Frühauf, Peter ; Kohout, Michal ; Lindner, Wolfgang</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c5061-7fee16302503b531d05529ffd31ce80a2db92faac1f2d93fcb360cd673cd66e13</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2013</creationdate><topic>Aminoethanol-based drugs</topic><topic>Analysis</topic><topic>Analytical chemistry</topic><topic>Biological and medical sciences</topic><topic>Cation Exchange Resins</topic><topic>Cation exchanging</topic><topic>Chemical synthesis</topic><topic>Chemistry</topic><topic>Chiral cation exchange</topic><topic>Chiral stationary phases</topic><topic>Chromatographic methods and physical methods associated with chromatography</topic><topic>Chromatography</topic><topic>Chromatography, High Pressure Liquid - instrumentation</topic><topic>Chromatography, Ion Exchange - instrumentation</topic><topic>Copper-catalyzed reactions</topic><topic>Cycloaddition</topic><topic>Density</topic><topic>Enantiomer separation</topic><topic>Exact sciences and technology</topic><topic>General pharmacology</topic><topic>Immobilization</topic><topic>Magnetic Resonance Spectroscopy</topic><topic>Medical sciences</topic><topic>Methyl alcohol</topic><topic>Other chromatographic methods</topic><topic>Pharmacology. Drug treatments</topic><topic>Phases</topic><topic>Spectrometry, Mass, Electrospray Ionization</topic><topic>Strategy</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Wolrab, Denise</creatorcontrib><creatorcontrib>Frühauf, Peter</creatorcontrib><creatorcontrib>Kohout, Michal</creatorcontrib><creatorcontrib>Lindner, Wolfgang</creatorcontrib><collection>Istex</collection><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>Solid State and Superconductivity Abstracts</collection><collection>Technology Research Database</collection><collection>Advanced Technologies Database with Aerospace</collection><collection>MEDLINE - Academic</collection><jtitle>Journal of separation science</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Wolrab, Denise</au><au>Frühauf, Peter</au><au>Kohout, Michal</au><au>Lindner, Wolfgang</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Click chemistry immobilization strategies in the development of strong cation exchanger chiral stationary phases for HPLC</atitle><jtitle>Journal of separation science</jtitle><addtitle>J. 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The performance of the novel SCX chiral stationary phases was evaluated under polar organic mode conditions with different ratios of methanol and acetonitrile, thereby changing the polarity of the bulk mobile phase. The type of co‐ and counterion additives employed in the mobile phase was varied as well. The influence of the formed 1,2,3‐triazol spacer as well as different substitution patterns in the benzene unit on the chiral recognition properties of the SOs is discussed.</abstract><cop>Weinheim</cop><pub>Blackwell Publishing Ltd</pub><pmid>23801658</pmid><doi>10.1002/jssc.201300559</doi><tpages>12</tpages></addata></record> |
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| subjects | Aminoethanol-based drugs Analysis Analytical chemistry Biological and medical sciences Cation Exchange Resins Cation exchanging Chemical synthesis Chemistry Chiral cation exchange Chiral stationary phases Chromatographic methods and physical methods associated with chromatography Chromatography Chromatography, High Pressure Liquid - instrumentation Chromatography, Ion Exchange - instrumentation Copper-catalyzed reactions Cycloaddition Density Enantiomer separation Exact sciences and technology General pharmacology Immobilization Magnetic Resonance Spectroscopy Medical sciences Methyl alcohol Other chromatographic methods Pharmacology. Drug treatments Phases Spectrometry, Mass, Electrospray Ionization Strategy |
| title | Click chemistry immobilization strategies in the development of strong cation exchanger chiral stationary phases for HPLC |
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