GR 24 Enantiomers: Synthesis, NMR Spectroscopy, X-ray Crystallography, and Separation by Chiral Electrokinetic Capillary Chromatography
Chiral discrimination of enantiomers of 2-methyl-4-(2-oxo-2,3,3a,8b-tetrahydro-4H-indeno[1,2b]furan-3-ylidenemethoxy)but-2-en-4-olide (commonly referred to as GR 24) by three polymeric chiral surfactants (PCS) is studied by use of chiral polymeric surfactant capillary electrophoresis (CPSCE). The CP...
Gespeichert in:
| Veröffentlicht in: | Analytical chemistry (Washington) 2000-08, Vol.72 (16), p.3887-3895 |
|---|---|
| Hauptverfasser: | , , , , , |
| Format: | Artikel |
| Sprache: | eng |
| Schlagworte: | |
| Online-Zugang: | Volltext |
| Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
| container_end_page | 3895 |
|---|---|
| container_issue | 16 |
| container_start_page | 3887 |
| container_title | Analytical chemistry (Washington) |
| container_volume | 72 |
| creator | Rugutt, Joseph K Yarabe, H. Hyacinthe Shamsi, Shahab A Billodeaux, Damon R Fronczek, Frank R Warner, Isiah M |
| description | Chiral discrimination of enantiomers of 2-methyl-4-(2-oxo-2,3,3a,8b-tetrahydro-4H-indeno[1,2b]furan-3-ylidenemethoxy)but-2-en-4-olide (commonly referred to as GR 24) by three polymeric chiral surfactants (PCS) is studied by use of chiral polymeric surfactant capillary electrophoresis (CPSCE). The CPSCE results indicate that the optical configurations of valine residues on the PCS backbone affect chiral resolution and elution order of GR24 stereoisomers. The l- and d-forms of poly(sodium N-undecanoyl valinate) provide baseline separation of all four enantiomers while the dl-form separates diastereomers of GR 24 (1). A model is presented rationalizing the migration behavior and chiral resolution of 1 in CPSCE. The actual configuration of the stereogenic centers of GR 24 and 3-[(2,5-dihydro-3-methyl-2-oxo-5-furanyl)oxo]methylene-3,3a,6,6a-tetrahydro-2H-cyclopenta[b]furan-2-one (GR 7) is established by a concerted application of high-resolution nuclear magnetic resonance spectroscopy and X-ray crystallography. |
| doi_str_mv | 10.1021/ac991438o |
| format | Article |
| fullrecord | <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_72207507</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>58114825</sourcerecordid><originalsourceid>FETCH-LOGICAL-a405t-1919901078dfca5cb67a247b023a8c10647d7565b3795a6a1582647a95270cbe3</originalsourceid><addsrcrecordid>eNplkc9uEzEQxi0EoqFw4AWQhQoSUhfG3vXa5oaitCCFAk2RerNmHYe43X_YG4ncuMJj8iQ4bNQiOI0085tP38xHyGMGLxlw9gqt1qzIVXeHTJjgkJVK8btkAgB5xiXAAXkQ4xUAY8DK--SAgRZaSzUhP0_PKS_orMV28F3jQnz96_sPuti2w9pFH4_p2ftzuuidHUIXbddvj-llFnBLp2EbB6zr7kvAfp3a2C7pwvUYMCm1tErI2ges6az-s33tWzd4S6fY-7rGsJuHrsFhr_CQ3FthHd2jfT0kn09mF9O32fzD6bvpm3mGBYghY5ppDQykWq4sCluVEnkhK-A5KsugLORSilJUudQCS2RC8dRDLdInbOXyQ_J81O1D93Xj4mAaH61LllrXbaKRnIMUIBP49B_wqtuENnkznEkNOZQ8QS9GyKb_xOBWpg--SdcZBmaXjrlJJ7FP9oKbqnHLv8gxjgQc7QGMFutVwNb6eMsVSqliZywbMR8H9-1mjOHalDKXwlx8XJgz9WnOy8uFOUn8s5FHG29v-N_fb2WNsi4</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>217903062</pqid></control><display><type>article</type><title>GR 24 Enantiomers: Synthesis, NMR Spectroscopy, X-ray Crystallography, and Separation by Chiral Electrokinetic Capillary Chromatography</title><source>MEDLINE</source><source>ACS Publications</source><creator>Rugutt, Joseph K ; Yarabe, H. Hyacinthe ; Shamsi, Shahab A ; Billodeaux, Damon R ; Fronczek, Frank R ; Warner, Isiah M</creator><creatorcontrib>Rugutt, Joseph K ; Yarabe, H. Hyacinthe ; Shamsi, Shahab A ; Billodeaux, Damon R ; Fronczek, Frank R ; Warner, Isiah M</creatorcontrib><description>Chiral discrimination of enantiomers of 2-methyl-4-(2-oxo-2,3,3a,8b-tetrahydro-4H-indeno[1,2b]furan-3-ylidenemethoxy)but-2-en-4-olide (commonly referred to as GR 24) by three polymeric chiral surfactants (PCS) is studied by use of chiral polymeric surfactant capillary electrophoresis (CPSCE). The CPSCE results indicate that the optical configurations of valine residues on the PCS backbone affect chiral resolution and elution order of GR24 stereoisomers. The l- and d-forms of poly(sodium N-undecanoyl valinate) provide baseline separation of all four enantiomers while the dl-form separates diastereomers of GR 24 (1). A model is presented rationalizing the migration behavior and chiral resolution of 1 in CPSCE. The actual configuration of the stereogenic centers of GR 24 and 3-[(2,5-dihydro-3-methyl-2-oxo-5-furanyl)oxo]methylene-3,3a,6,6a-tetrahydro-2H-cyclopenta[b]furan-2-one (GR 7) is established by a concerted application of high-resolution nuclear magnetic resonance spectroscopy and X-ray crystallography.</description><identifier>ISSN: 0003-2700</identifier><identifier>EISSN: 1520-6882</identifier><identifier>DOI: 10.1021/ac991438o</identifier><identifier>PMID: 10959978</identifier><identifier>CODEN: ANCHAM</identifier><language>eng</language><publisher>Washington, DC: American Chemical Society</publisher><subject>Chemistry ; Chromatography ; Chromatography, Micellar Electrokinetic Capillary ; Condensed matter: structure, mechanical and thermal properties ; Crystallography ; Crystallography, X-Ray ; Exact sciences and technology ; Heterocyclic compounds ; Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives ; Lactones - chemical synthesis ; Lactones - chemistry ; Magnetic Resonance Spectroscopy ; NMR ; Nuclear magnetic resonance ; Organic chemistry ; Organic compounds ; Parasites ; Physics ; Polymers ; Preparations and properties ; Stereoisomerism ; Structure of solids and liquids; crystallography ; Structure of specific crystalline solids ; X-rays</subject><ispartof>Analytical chemistry (Washington), 2000-08, Vol.72 (16), p.3887-3895</ispartof><rights>Copyright © 2000 American Chemical Society</rights><rights>2000 INIST-CNRS</rights><rights>Copyright American Chemical Society Aug 15, 2000</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a405t-1919901078dfca5cb67a247b023a8c10647d7565b3795a6a1582647a95270cbe3</citedby><cites>FETCH-LOGICAL-a405t-1919901078dfca5cb67a247b023a8c10647d7565b3795a6a1582647a95270cbe3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://pubs.acs.org/doi/pdf/10.1021/ac991438o$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/ac991438o$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,776,780,2751,27055,27903,27904,56717,56767</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=1488847$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/10959978$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Rugutt, Joseph K</creatorcontrib><creatorcontrib>Yarabe, H. Hyacinthe</creatorcontrib><creatorcontrib>Shamsi, Shahab A</creatorcontrib><creatorcontrib>Billodeaux, Damon R</creatorcontrib><creatorcontrib>Fronczek, Frank R</creatorcontrib><creatorcontrib>Warner, Isiah M</creatorcontrib><title>GR 24 Enantiomers: Synthesis, NMR Spectroscopy, X-ray Crystallography, and Separation by Chiral Electrokinetic Capillary Chromatography</title><title>Analytical chemistry (Washington)</title><addtitle>Anal. Chem</addtitle><description>Chiral discrimination of enantiomers of 2-methyl-4-(2-oxo-2,3,3a,8b-tetrahydro-4H-indeno[1,2b]furan-3-ylidenemethoxy)but-2-en-4-olide (commonly referred to as GR 24) by three polymeric chiral surfactants (PCS) is studied by use of chiral polymeric surfactant capillary electrophoresis (CPSCE). The CPSCE results indicate that the optical configurations of valine residues on the PCS backbone affect chiral resolution and elution order of GR24 stereoisomers. The l- and d-forms of poly(sodium N-undecanoyl valinate) provide baseline separation of all four enantiomers while the dl-form separates diastereomers of GR 24 (1). A model is presented rationalizing the migration behavior and chiral resolution of 1 in CPSCE. The actual configuration of the stereogenic centers of GR 24 and 3-[(2,5-dihydro-3-methyl-2-oxo-5-furanyl)oxo]methylene-3,3a,6,6a-tetrahydro-2H-cyclopenta[b]furan-2-one (GR 7) is established by a concerted application of high-resolution nuclear magnetic resonance spectroscopy and X-ray crystallography.</description><subject>Chemistry</subject><subject>Chromatography</subject><subject>Chromatography, Micellar Electrokinetic Capillary</subject><subject>Condensed matter: structure, mechanical and thermal properties</subject><subject>Crystallography</subject><subject>Crystallography, X-Ray</subject><subject>Exact sciences and technology</subject><subject>Heterocyclic compounds</subject><subject>Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives</subject><subject>Lactones - chemical synthesis</subject><subject>Lactones - chemistry</subject><subject>Magnetic Resonance Spectroscopy</subject><subject>NMR</subject><subject>Nuclear magnetic resonance</subject><subject>Organic chemistry</subject><subject>Organic compounds</subject><subject>Parasites</subject><subject>Physics</subject><subject>Polymers</subject><subject>Preparations and properties</subject><subject>Stereoisomerism</subject><subject>Structure of solids and liquids; crystallography</subject><subject>Structure of specific crystalline solids</subject><subject>X-rays</subject><issn>0003-2700</issn><issn>1520-6882</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2000</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNplkc9uEzEQxi0EoqFw4AWQhQoSUhfG3vXa5oaitCCFAk2RerNmHYe43X_YG4ncuMJj8iQ4bNQiOI0085tP38xHyGMGLxlw9gqt1qzIVXeHTJjgkJVK8btkAgB5xiXAAXkQ4xUAY8DK--SAgRZaSzUhP0_PKS_orMV28F3jQnz96_sPuti2w9pFH4_p2ftzuuidHUIXbddvj-llFnBLp2EbB6zr7kvAfp3a2C7pwvUYMCm1tErI2ges6az-s33tWzd4S6fY-7rGsJuHrsFhr_CQ3FthHd2jfT0kn09mF9O32fzD6bvpm3mGBYghY5ppDQykWq4sCluVEnkhK-A5KsugLORSilJUudQCS2RC8dRDLdInbOXyQ_J81O1D93Xj4mAaH61LllrXbaKRnIMUIBP49B_wqtuENnkznEkNOZQ8QS9GyKb_xOBWpg--SdcZBmaXjrlJJ7FP9oKbqnHLv8gxjgQc7QGMFutVwNb6eMsVSqliZywbMR8H9-1mjOHalDKXwlx8XJgz9WnOy8uFOUn8s5FHG29v-N_fb2WNsi4</recordid><startdate>20000815</startdate><enddate>20000815</enddate><creator>Rugutt, Joseph K</creator><creator>Yarabe, H. Hyacinthe</creator><creator>Shamsi, Shahab A</creator><creator>Billodeaux, Damon R</creator><creator>Fronczek, Frank R</creator><creator>Warner, Isiah M</creator><general>American Chemical Society</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>7QF</scope><scope>7QO</scope><scope>7QQ</scope><scope>7SC</scope><scope>7SE</scope><scope>7SP</scope><scope>7SR</scope><scope>7TA</scope><scope>7TB</scope><scope>7TM</scope><scope>7U5</scope><scope>7U7</scope><scope>7U9</scope><scope>8BQ</scope><scope>8FD</scope><scope>C1K</scope><scope>F28</scope><scope>FR3</scope><scope>H8D</scope><scope>H8G</scope><scope>H94</scope><scope>JG9</scope><scope>JQ2</scope><scope>KR7</scope><scope>L7M</scope><scope>L~C</scope><scope>L~D</scope><scope>P64</scope><scope>7X8</scope></search><sort><creationdate>20000815</creationdate><title>GR 24 Enantiomers: Synthesis, NMR Spectroscopy, X-ray Crystallography, and Separation by Chiral Electrokinetic Capillary Chromatography</title><author>Rugutt, Joseph K ; Yarabe, H. Hyacinthe ; Shamsi, Shahab A ; Billodeaux, Damon R ; Fronczek, Frank R ; Warner, Isiah M</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a405t-1919901078dfca5cb67a247b023a8c10647d7565b3795a6a1582647a95270cbe3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2000</creationdate><topic>Chemistry</topic><topic>Chromatography</topic><topic>Chromatography, Micellar Electrokinetic Capillary</topic><topic>Condensed matter: structure, mechanical and thermal properties</topic><topic>Crystallography</topic><topic>Crystallography, X-Ray</topic><topic>Exact sciences and technology</topic><topic>Heterocyclic compounds</topic><topic>Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives</topic><topic>Lactones - chemical synthesis</topic><topic>Lactones - chemistry</topic><topic>Magnetic Resonance Spectroscopy</topic><topic>NMR</topic><topic>Nuclear magnetic resonance</topic><topic>Organic chemistry</topic><topic>Organic compounds</topic><topic>Parasites</topic><topic>Physics</topic><topic>Polymers</topic><topic>Preparations and properties</topic><topic>Stereoisomerism</topic><topic>Structure of solids and liquids; crystallography</topic><topic>Structure of specific crystalline solids</topic><topic>X-rays</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Rugutt, Joseph K</creatorcontrib><creatorcontrib>Yarabe, H. Hyacinthe</creatorcontrib><creatorcontrib>Shamsi, Shahab A</creatorcontrib><creatorcontrib>Billodeaux, Damon R</creatorcontrib><creatorcontrib>Fronczek, Frank R</creatorcontrib><creatorcontrib>Warner, Isiah M</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>Aluminium Industry Abstracts</collection><collection>Biotechnology Research Abstracts</collection><collection>Ceramic Abstracts</collection><collection>Computer and Information Systems Abstracts</collection><collection>Corrosion Abstracts</collection><collection>Electronics & Communications Abstracts</collection><collection>Engineered Materials Abstracts</collection><collection>Materials Business File</collection><collection>Mechanical & Transportation Engineering Abstracts</collection><collection>Nucleic Acids Abstracts</collection><collection>Solid State and Superconductivity Abstracts</collection><collection>Toxicology Abstracts</collection><collection>Virology and AIDS Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Environmental Sciences and Pollution Management</collection><collection>ANTE: Abstracts in New Technology & Engineering</collection><collection>Engineering Research Database</collection><collection>Aerospace Database</collection><collection>Copper Technical Reference Library</collection><collection>AIDS and Cancer Research Abstracts</collection><collection>Materials Research Database</collection><collection>ProQuest Computer Science Collection</collection><collection>Civil Engineering Abstracts</collection><collection>Advanced Technologies Database with Aerospace</collection><collection>Computer and Information Systems Abstracts Academic</collection><collection>Computer and Information Systems Abstracts Professional</collection><collection>Biotechnology and BioEngineering Abstracts</collection><collection>MEDLINE - Academic</collection><jtitle>Analytical chemistry (Washington)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Rugutt, Joseph K</au><au>Yarabe, H. Hyacinthe</au><au>Shamsi, Shahab A</au><au>Billodeaux, Damon R</au><au>Fronczek, Frank R</au><au>Warner, Isiah M</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>GR 24 Enantiomers: Synthesis, NMR Spectroscopy, X-ray Crystallography, and Separation by Chiral Electrokinetic Capillary Chromatography</atitle><jtitle>Analytical chemistry (Washington)</jtitle><addtitle>Anal. Chem</addtitle><date>2000-08-15</date><risdate>2000</risdate><volume>72</volume><issue>16</issue><spage>3887</spage><epage>3895</epage><pages>3887-3895</pages><issn>0003-2700</issn><eissn>1520-6882</eissn><coden>ANCHAM</coden><abstract>Chiral discrimination of enantiomers of 2-methyl-4-(2-oxo-2,3,3a,8b-tetrahydro-4H-indeno[1,2b]furan-3-ylidenemethoxy)but-2-en-4-olide (commonly referred to as GR 24) by three polymeric chiral surfactants (PCS) is studied by use of chiral polymeric surfactant capillary electrophoresis (CPSCE). The CPSCE results indicate that the optical configurations of valine residues on the PCS backbone affect chiral resolution and elution order of GR24 stereoisomers. The l- and d-forms of poly(sodium N-undecanoyl valinate) provide baseline separation of all four enantiomers while the dl-form separates diastereomers of GR 24 (1). A model is presented rationalizing the migration behavior and chiral resolution of 1 in CPSCE. The actual configuration of the stereogenic centers of GR 24 and 3-[(2,5-dihydro-3-methyl-2-oxo-5-furanyl)oxo]methylene-3,3a,6,6a-tetrahydro-2H-cyclopenta[b]furan-2-one (GR 7) is established by a concerted application of high-resolution nuclear magnetic resonance spectroscopy and X-ray crystallography.</abstract><cop>Washington, DC</cop><pub>American Chemical Society</pub><pmid>10959978</pmid><doi>10.1021/ac991438o</doi><tpages>9</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0003-2700 |
| ispartof | Analytical chemistry (Washington), 2000-08, Vol.72 (16), p.3887-3895 |
| issn | 0003-2700 1520-6882 |
| language | eng |
| recordid | cdi_proquest_miscellaneous_72207507 |
| source | MEDLINE; ACS Publications |
| subjects | Chemistry Chromatography Chromatography, Micellar Electrokinetic Capillary Condensed matter: structure, mechanical and thermal properties Crystallography Crystallography, X-Ray Exact sciences and technology Heterocyclic compounds Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives Lactones - chemical synthesis Lactones - chemistry Magnetic Resonance Spectroscopy NMR Nuclear magnetic resonance Organic chemistry Organic compounds Parasites Physics Polymers Preparations and properties Stereoisomerism Structure of solids and liquids crystallography Structure of specific crystalline solids X-rays |
| title | GR 24 Enantiomers: Synthesis, NMR Spectroscopy, X-ray Crystallography, and Separation by Chiral Electrokinetic Capillary Chromatography |
| url | https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-21T14%3A31%3A45IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-proquest_cross&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=GR%2024%20Enantiomers:%E2%80%89%20Synthesis,%20NMR%20Spectroscopy,%20X-ray%20Crystallography,%20and%20Separation%20by%20Chiral%20Electrokinetic%20Capillary%20Chromatography&rft.jtitle=Analytical%20chemistry%20(Washington)&rft.au=Rugutt,%20Joseph%20K&rft.date=2000-08-15&rft.volume=72&rft.issue=16&rft.spage=3887&rft.epage=3895&rft.pages=3887-3895&rft.issn=0003-2700&rft.eissn=1520-6882&rft.coden=ANCHAM&rft_id=info:doi/10.1021/ac991438o&rft_dat=%3Cproquest_cross%3E58114825%3C/proquest_cross%3E%3Curl%3E%3C/url%3E&disable_directlink=true&sfx.directlink=off&sfx.report_link=0&rft_id=info:oai/&rft_pqid=217903062&rft_id=info:pmid/10959978&rfr_iscdi=true |