Steric effects on the enantiodiscrimination of diproline chiral stationary phases in the resolution of racemic compounds
Eight diproline chiral stationary phases with different end-capping groups were prepared and evaluated for the enantio-selective resolution of 41 racemic analytes. The end-capping group on the N-terminal of the peptide proved to be important as the chiral separation efficiency was decreased signific...
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| Veröffentlicht in: | Journal of Chromatography A 2011-08, Vol.1218 (32), p.5498-5503 |
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| creator | Dai, Zhi Ye, Guozhong Pittman, Charles U. Li, Tingyu |
| description | Eight diproline chiral stationary phases with different end-capping groups were prepared and evaluated for the enantio-selective resolution of 41 racemic analytes. The end-capping group on the N-terminal of the peptide proved to be important as the chiral separation efficiency was decreased significantly without it. In general, increasing steric bulkiness near the N-terminal of diproline increases the enantioselectivity. Electronic structures of the end-capping groups are also important. One stationary phase with an adamantanecarbonyl capping group was found to provide both higher average separation and resolution factors than our previous leader. Three other stationary phases with 2-methylpropanoyl, cyclopropanecarbonyl and cyclobutanecarbonyl end capping groups were found to provide comparable average separation factor but higher resolution factors than our previous leader. |
| doi_str_mv | 10.1016/j.chroma.2011.06.047 |
| format | Article |
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The end-capping group on the N-terminal of the peptide proved to be important as the chiral separation efficiency was decreased significantly without it. In general, increasing steric bulkiness near the N-terminal of diproline increases the enantioselectivity. Electronic structures of the end-capping groups are also important. One stationary phase with an adamantanecarbonyl capping group was found to provide both higher average separation and resolution factors than our previous leader. 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All rights reserved. 2011</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c582t-6b8dd85cd6670257deac9b77c1a860b92f261d1825c9c23ee282cc34ec4387da3</citedby><cites>FETCH-LOGICAL-c582t-6b8dd85cd6670257deac9b77c1a860b92f261d1825c9c23ee282cc34ec4387da3</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.2011.06.047$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>230,314,780,784,885,3550,27924,27925,45995</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=24370934$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/21741656$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Dai, Zhi</creatorcontrib><creatorcontrib>Ye, Guozhong</creatorcontrib><creatorcontrib>Pittman, Charles U.</creatorcontrib><creatorcontrib>Li, Tingyu</creatorcontrib><title>Steric effects on the enantiodiscrimination of diproline chiral stationary phases in the resolution of racemic compounds</title><title>Journal of Chromatography A</title><addtitle>J Chromatogr A</addtitle><description>Eight diproline chiral stationary phases with different end-capping groups were prepared and evaluated for the enantio-selective resolution of 41 racemic analytes. The end-capping group on the N-terminal of the peptide proved to be important as the chiral separation efficiency was decreased significantly without it. In general, increasing steric bulkiness near the N-terminal of diproline increases the enantioselectivity. Electronic structures of the end-capping groups are also important. One stationary phase with an adamantanecarbonyl capping group was found to provide both higher average separation and resolution factors than our previous leader. Three other stationary phases with 2-methylpropanoyl, cyclopropanecarbonyl and cyclobutanecarbonyl end capping groups were found to provide comparable average separation factor but higher resolution factors than our previous leader.</description><subject>Adsorption</subject><subject>Analytical chemistry</subject><subject>Capping</subject><subject>Chemistry</subject><subject>Chromatographic methods and physical methods associated with chromatography</subject><subject>Chromatography</subject><subject>Chromatography, High Pressure Liquid - instrumentation</subject><subject>Chromatography, High Pressure Liquid - methods</subject><subject>Electronic structure</subject><subject>enantiomers</subject><subject>Exact sciences and technology</subject><subject>Organic Chemicals - chemistry</subject><subject>Other chromatographic methods</subject><subject>Peptide stationary phase</subject><subject>Peptides</subject><subject>Phases</subject><subject>Proline</subject><subject>Proline - analogs & derivatives</subject><subject>Proline - chemistry</subject><subject>Proline chiral stationary phase</subject><subject>Proline enantioselective stationary phase</subject><subject>Separation</subject><subject>Stereoisomerism</subject><subject>Steric effect</subject><subject>Steric effects</subject><issn>0021-9673</issn><issn>1873-3778</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2011</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqFkk1v1DAQhiMEokvhHyDIBYnLBn_Fdi5IVcWXVIlD6dnyjieNV4kd7KSCf4_Lblu4wMWWNc_MvDOvq-olJQ0lVL7bNzCkONmGEUobIhsi1KNqQ7XiW66UflxtCGF020nFT6pnOe8JoYoo9rQ6YVQJKlu5qX5cLpg81Nj3CEuuY6iXAWsMNiw-Op8h-ckHWx6hjn3t_Jzi6APWMPhkxzovv2M2_aznwWbMtT-USJjjuN7lJQs4lT4QpzmuweXn1ZPejhlfHO_T6urjh2_nn7cXXz99OT-72EKr2bKVO-2cbsFJqQhrlUML3U4poFZLsutYzyR1VLMWOmAckWkGwAWC4Fo5y0-r94e687qb0AGGpcg2cxmraDbRevN3JPjBXMcbw2krysJKgbfHAil-XzEvZipbwXG0AeOaDZWCcdaycv4XZWWKlulOF1QcUEgx54T9vSJKzK2_Zm8O_ppbfw2Rpvhb0l79Oc190p2hBXhzBGwGO_bJBvD5gRNckY6Lwr0-cL2Nxl6nwlxdlk5t-SSaCCIeFofFnRuPyWTwGACdT-WrGBf9v7X-Aj1i0i8</recordid><startdate>20110812</startdate><enddate>20110812</enddate><creator>Dai, Zhi</creator><creator>Ye, Guozhong</creator><creator>Pittman, Charles U.</creator><creator>Li, Tingyu</creator><general>Elsevier B.V</general><general>Elsevier</general><scope>FBQ</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>7QH</scope><scope>7UA</scope><scope>C1K</scope><scope>F1W</scope><scope>H97</scope><scope>L.G</scope><scope>7U5</scope><scope>8FD</scope><scope>L7M</scope><scope>5PM</scope></search><sort><creationdate>20110812</creationdate><title>Steric effects on the enantiodiscrimination of diproline chiral stationary phases in the resolution of racemic compounds</title><author>Dai, Zhi ; Ye, Guozhong ; Pittman, Charles U. ; Li, Tingyu</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c582t-6b8dd85cd6670257deac9b77c1a860b92f261d1825c9c23ee282cc34ec4387da3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2011</creationdate><topic>Adsorption</topic><topic>Analytical chemistry</topic><topic>Capping</topic><topic>Chemistry</topic><topic>Chromatographic methods and physical methods associated with chromatography</topic><topic>Chromatography</topic><topic>Chromatography, High Pressure Liquid - instrumentation</topic><topic>Chromatography, High Pressure Liquid - methods</topic><topic>Electronic structure</topic><topic>enantiomers</topic><topic>Exact sciences and technology</topic><topic>Organic Chemicals - chemistry</topic><topic>Other chromatographic methods</topic><topic>Peptide stationary phase</topic><topic>Peptides</topic><topic>Phases</topic><topic>Proline</topic><topic>Proline - analogs & derivatives</topic><topic>Proline - chemistry</topic><topic>Proline chiral stationary phase</topic><topic>Proline enantioselective stationary phase</topic><topic>Separation</topic><topic>Stereoisomerism</topic><topic>Steric effect</topic><topic>Steric effects</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Dai, Zhi</creatorcontrib><creatorcontrib>Ye, Guozhong</creatorcontrib><creatorcontrib>Pittman, Charles U.</creatorcontrib><creatorcontrib>Li, Tingyu</creatorcontrib><collection>AGRIS</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>Aqualine</collection><collection>Water Resources Abstracts</collection><collection>Environmental Sciences and Pollution Management</collection><collection>ASFA: Aquatic Sciences and Fisheries Abstracts</collection><collection>Aquatic Science & Fisheries Abstracts (ASFA) 3: Aquatic Pollution & Environmental Quality</collection><collection>Aquatic Science & Fisheries Abstracts (ASFA) Professional</collection><collection>Solid State and Superconductivity Abstracts</collection><collection>Technology Research Database</collection><collection>Advanced Technologies Database with Aerospace</collection><collection>PubMed Central (Full Participant titles)</collection><jtitle>Journal of Chromatography A</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Dai, Zhi</au><au>Ye, Guozhong</au><au>Pittman, Charles U.</au><au>Li, Tingyu</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Steric effects on the enantiodiscrimination of diproline chiral stationary phases in the resolution of racemic compounds</atitle><jtitle>Journal of Chromatography A</jtitle><addtitle>J Chromatogr A</addtitle><date>2011-08-12</date><risdate>2011</risdate><volume>1218</volume><issue>32</issue><spage>5498</spage><epage>5503</epage><pages>5498-5503</pages><issn>0021-9673</issn><eissn>1873-3778</eissn><coden>JOCRAM</coden><abstract>Eight diproline chiral stationary phases with different end-capping groups were prepared and evaluated for the enantio-selective resolution of 41 racemic analytes. The end-capping group on the N-terminal of the peptide proved to be important as the chiral separation efficiency was decreased significantly without it. In general, increasing steric bulkiness near the N-terminal of diproline increases the enantioselectivity. Electronic structures of the end-capping groups are also important. One stationary phase with an adamantanecarbonyl capping group was found to provide both higher average separation and resolution factors than our previous leader. Three other stationary phases with 2-methylpropanoyl, cyclopropanecarbonyl and cyclobutanecarbonyl end capping groups were found to provide comparable average separation factor but higher resolution factors than our previous leader.</abstract><cop>Amsterdam</cop><pub>Elsevier B.V</pub><pmid>21741656</pmid><doi>10.1016/j.chroma.2011.06.047</doi><tpages>6</tpages><oa>free_for_read</oa></addata></record> |
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| subjects | Adsorption Analytical chemistry Capping Chemistry Chromatographic methods and physical methods associated with chromatography Chromatography Chromatography, High Pressure Liquid - instrumentation Chromatography, High Pressure Liquid - methods Electronic structure enantiomers Exact sciences and technology Organic Chemicals - chemistry Other chromatographic methods Peptide stationary phase Peptides Phases Proline Proline - analogs & derivatives Proline - chemistry Proline chiral stationary phase Proline enantioselective stationary phase Separation Stereoisomerism Steric effect Steric effects |
| title | Steric effects on the enantiodiscrimination of diproline chiral stationary phases in the resolution of racemic compounds |
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