A conformational study of a biologically active conjugated syn-oxime
The conjugated system (E)‐tiglaldoxime is the simplest example of a perillartine analog which exhibits sweetness with a taste potency greater than sucrose with almost no bitter aftertaste. In previous studies, the structure of this biologically active compound has been assumed to be planar with the...
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| Veröffentlicht in: | Journal of computational chemistry 1988-01, Vol.9 (1), p.67-74 |
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| container_title | Journal of computational chemistry |
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| creator | Venanzi, Thomas J. Venanzi, Carol A. |
| description | The conjugated system (E)‐tiglaldoxime is the simplest example of a perillartine analog which exhibits sweetness with a taste potency greater than sucrose with almost no bitter aftertaste. In previous studies, the structure of this biologically active compound has been assumed to be planar with the CC double bond trans to the CN bond of the oxime moiety. In this article a conformational analysis of this molecule is reported. The results indicate that, although the trans conformer of the planar molecule is indeed the global minimum, other conformers lie within a few kilocalories of this minimum. Hence, other accessible conformations may be available for interaction with the receptor and, therefore, may be biologically active. The structural parameters obtained for this conjugated syn‐oxime are nearly identical to those of (E)‐acetaldoxime. This fact has implications for the transferability of these parameters to the more complicated perillartine analogs. |
| doi_str_mv | 10.1002/jcc.540090109 |
| format | Article |
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In previous studies, the structure of this biologically active compound has been assumed to be planar with the CC double bond trans to the CN bond of the oxime moiety. In this article a conformational analysis of this molecule is reported. The results indicate that, although the trans conformer of the planar molecule is indeed the global minimum, other conformers lie within a few kilocalories of this minimum. Hence, other accessible conformations may be available for interaction with the receptor and, therefore, may be biologically active. The structural parameters obtained for this conjugated syn‐oxime are nearly identical to those of (E)‐acetaldoxime. This fact has implications for the transferability of these parameters to the more complicated perillartine analogs.</description><identifier>ISSN: 0192-8651</identifier><identifier>EISSN: 1096-987X</identifier><identifier>DOI: 10.1002/jcc.540090109</identifier><identifier>CODEN: JCCHDD</identifier><language>eng</language><publisher>New York: John Wiley & Sons, Inc</publisher><subject>Ab initio calculations ; Atomic and molecular physics ; Calculations and mathematical techniques in atomic and molecular physics (excluding electron correlation calculations) ; Electronic structure of atoms, molecules and their ions: theory ; Exact sciences and technology ; Physics</subject><ispartof>Journal of computational chemistry, 1988-01, Vol.9 (1), p.67-74</ispartof><rights>Copyright © 1988 John Wiley & Sons, Inc.</rights><rights>1988 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c3509-c5df06e1d9a3ff930b0b7baccaae68141cebe21d048d5b55b4c1634b9df2c0db3</citedby><cites>FETCH-LOGICAL-c3509-c5df06e1d9a3ff930b0b7baccaae68141cebe21d048d5b55b4c1634b9df2c0db3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1002%2Fjcc.540090109$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fjcc.540090109$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,776,780,1411,4010,27900,27901,27902,45550,45551</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=7764036$$DView record in Pascal Francis$$Hfree_for_read</backlink></links><search><creatorcontrib>Venanzi, Thomas J.</creatorcontrib><creatorcontrib>Venanzi, Carol A.</creatorcontrib><title>A conformational study of a biologically active conjugated syn-oxime</title><title>Journal of computational chemistry</title><addtitle>J. Comput. Chem</addtitle><description>The conjugated system (E)‐tiglaldoxime is the simplest example of a perillartine analog which exhibits sweetness with a taste potency greater than sucrose with almost no bitter aftertaste. In previous studies, the structure of this biologically active compound has been assumed to be planar with the CC double bond trans to the CN bond of the oxime moiety. In this article a conformational analysis of this molecule is reported. The results indicate that, although the trans conformer of the planar molecule is indeed the global minimum, other conformers lie within a few kilocalories of this minimum. Hence, other accessible conformations may be available for interaction with the receptor and, therefore, may be biologically active. The structural parameters obtained for this conjugated syn‐oxime are nearly identical to those of (E)‐acetaldoxime. This fact has implications for the transferability of these parameters to the more complicated perillartine analogs.</description><subject>Ab initio calculations</subject><subject>Atomic and molecular physics</subject><subject>Calculations and mathematical techniques in atomic and molecular physics (excluding electron correlation calculations)</subject><subject>Electronic structure of atoms, molecules and their ions: theory</subject><subject>Exact sciences and technology</subject><subject>Physics</subject><issn>0192-8651</issn><issn>1096-987X</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>1988</creationdate><recordtype>article</recordtype><recordid>eNp9kDFPwzAQhS0EEqUwsmdgTTnHsROPVQqFqioDINgs27ErlzSu4hSaf0-qVhUTy93yvXf3HkK3GEYYILlfaT2iKQAHDPwMDfrJYp5nn-doAJgncc4ovkRXIawAgFCWDtBkHGlfW9-sZet8LasotNuyi7yNZKScr_zSaVlVXSR1677Nnl5tl7I1ZRS6OvY7tzbX6MLKKpib4x6i98eHt-Ipnr9Mn4vxPNaEAo81LS0wg0suibWcgAKVKam1lIblOMXaKJPgEtK8pIpSlWrMSKp4aRMNpSJDFB98deNDaIwVm8atZdMJDGJfgegrEKcKev7uwG9k6EPYRtbahZMoy1gKhPVYdsB-XGW6_z3FrCj-Hjg-5EJrdielbL4Ey0hGxcdiKhZ4RsnkdSoI-QUxdnxW</recordid><startdate>198801</startdate><enddate>198801</enddate><creator>Venanzi, Thomas J.</creator><creator>Venanzi, Carol A.</creator><general>John Wiley & Sons, Inc</general><general>Wiley</general><scope>BSCLL</scope><scope>IQODW</scope><scope>AAYXX</scope><scope>CITATION</scope></search><sort><creationdate>198801</creationdate><title>A conformational study of a biologically active conjugated syn-oxime</title><author>Venanzi, Thomas J. ; Venanzi, Carol A.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c3509-c5df06e1d9a3ff930b0b7baccaae68141cebe21d048d5b55b4c1634b9df2c0db3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>1988</creationdate><topic>Ab initio calculations</topic><topic>Atomic and molecular physics</topic><topic>Calculations and mathematical techniques in atomic and molecular physics (excluding electron correlation calculations)</topic><topic>Electronic structure of atoms, molecules and their ions: theory</topic><topic>Exact sciences and technology</topic><topic>Physics</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Venanzi, Thomas J.</creatorcontrib><creatorcontrib>Venanzi, Carol A.</creatorcontrib><collection>Istex</collection><collection>Pascal-Francis</collection><collection>CrossRef</collection><jtitle>Journal of computational chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Venanzi, Thomas J.</au><au>Venanzi, Carol A.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>A conformational study of a biologically active conjugated syn-oxime</atitle><jtitle>Journal of computational chemistry</jtitle><addtitle>J. Comput. Chem</addtitle><date>1988-01</date><risdate>1988</risdate><volume>9</volume><issue>1</issue><spage>67</spage><epage>74</epage><pages>67-74</pages><issn>0192-8651</issn><eissn>1096-987X</eissn><coden>JCCHDD</coden><abstract>The conjugated system (E)‐tiglaldoxime is the simplest example of a perillartine analog which exhibits sweetness with a taste potency greater than sucrose with almost no bitter aftertaste. In previous studies, the structure of this biologically active compound has been assumed to be planar with the CC double bond trans to the CN bond of the oxime moiety. In this article a conformational analysis of this molecule is reported. The results indicate that, although the trans conformer of the planar molecule is indeed the global minimum, other conformers lie within a few kilocalories of this minimum. Hence, other accessible conformations may be available for interaction with the receptor and, therefore, may be biologically active. The structural parameters obtained for this conjugated syn‐oxime are nearly identical to those of (E)‐acetaldoxime. This fact has implications for the transferability of these parameters to the more complicated perillartine analogs.</abstract><cop>New York</cop><pub>John Wiley & Sons, Inc</pub><doi>10.1002/jcc.540090109</doi><tpages>8</tpages></addata></record> |
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| language | eng |
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| source | Wiley Online Library All Journals |
| subjects | Ab initio calculations Atomic and molecular physics Calculations and mathematical techniques in atomic and molecular physics (excluding electron correlation calculations) Electronic structure of atoms, molecules and their ions: theory Exact sciences and technology Physics |
| title | A conformational study of a biologically active conjugated syn-oxime |
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