Synchronized Chiral Induction between [5]Helicene–Spermine Ligand and B–Z DNA Transition
The 2,13‐dimethoxy[5]helicene–spermine ligand 8 b possesses an axial chirality. The racemic 8 b was bound to B‐DNA by the accompanying induction of its (P)‐chirality together with the B‐to‐Z helicity change of the duplex DNA, [(dC‐dG)3]2. The (P)‐chirality of the bound 8 b, in turn, transitioned to...
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| Veröffentlicht in: | Chemistry : a European journal 2017-02, Vol.23 (8), p.1763-1769 |
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| creator | Kawara, Kensuke Tsuji, Genichiro Taniguchi, Yosuke Sasaki, Shigeki |
| description | The 2,13‐dimethoxy[5]helicene–spermine ligand 8 b possesses an axial chirality. The racemic 8 b was bound to B‐DNA by the accompanying induction of its (P)‐chirality together with the B‐to‐Z helicity change of the duplex DNA, [(dC‐dG)3]2. The (P)‐chirality of the bound 8 b, in turn, transitioned to the (M)‐chirality according to the Z‐helicity of the DNA. These results illustrate the chirality synchronization between the DNA and the ligand.
Let′s twist again! The 2,13‐dimethoxy[5]helicene–spermine ligand 8 b possesses an axial chirality. The racemic 8 b was bound to B‐DNA with accompanying induction of its (P)‐chirality together with the B‐to‐Z helicity change of the duplex DNA, [(dC‐dG)3]2. The (P)‐chirality of the bound 8 b, in turn, transitioned to the (M)‐chirality according to the Z‐helicity of DNA. These results have illustrated the chirality synchronization between the DNA and ligand. |
| doi_str_mv | 10.1002/chem.201605276 |
| format | Article |
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Let′s twist again! The 2,13‐dimethoxy[5]helicene–spermine ligand 8 b possesses an axial chirality. The racemic 8 b was bound to B‐DNA with accompanying induction of its (P)‐chirality together with the B‐to‐Z helicity change of the duplex DNA, [(dC‐dG)3]2. The (P)‐chirality of the bound 8 b, in turn, transitioned to the (M)‐chirality according to the Z‐helicity of DNA. These results have illustrated the chirality synchronization between the DNA and ligand.</description><identifier>ISSN: 0947-6539</identifier><identifier>EISSN: 1521-3765</identifier><identifier>DOI: 10.1002/chem.201605276</identifier><identifier>PMID: 27943481</identifier><identifier>CODEN: CEUJED</identifier><language>eng</language><publisher>Germany: Wiley Subscription Services, Inc</publisher><subject>B–Z transition ; Chemistry ; Chirality ; Circular Dichroism ; Deoxyribonucleic acid ; DNA ; DNA, B-Form - chemistry ; DNA, B-Form - metabolism ; DNA, Z-Form - chemistry ; DNA, Z-Form - metabolism ; helicene ; Helicity ; Ligands ; Molecular Conformation ; Nucleic Acid Conformation ; Polycyclic Compounds - chemistry ; Polycyclic Compounds - metabolism ; Spermine - chemistry ; Spermine - metabolism ; Stereoisomerism ; Synchronism ; Synchronization ; Thermodynamics</subject><ispartof>Chemistry : a European journal, 2017-02, Vol.23 (8), p.1763-1769</ispartof><rights>2017 Wiley‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><rights>2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.</rights><rights>2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c5426-b866d47c9805436146041a6f26fc0dc0003d0f9f4601247dc0bfa9900a7b1283</citedby><cites>FETCH-LOGICAL-c5426-b866d47c9805436146041a6f26fc0dc0003d0f9f4601247dc0bfa9900a7b1283</cites><orcidid>0000-0002-8985-3629 ; 0000-0003-2013-2441</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1002%2Fchem.201605276$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fchem.201605276$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,776,780,1411,27903,27904,45553,45554</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/27943481$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Kawara, Kensuke</creatorcontrib><creatorcontrib>Tsuji, Genichiro</creatorcontrib><creatorcontrib>Taniguchi, Yosuke</creatorcontrib><creatorcontrib>Sasaki, Shigeki</creatorcontrib><title>Synchronized Chiral Induction between [5]Helicene–Spermine Ligand and B–Z DNA Transition</title><title>Chemistry : a European journal</title><addtitle>Chemistry</addtitle><description>The 2,13‐dimethoxy[5]helicene–spermine ligand 8 b possesses an axial chirality. The racemic 8 b was bound to B‐DNA by the accompanying induction of its (P)‐chirality together with the B‐to‐Z helicity change of the duplex DNA, [(dC‐dG)3]2. The (P)‐chirality of the bound 8 b, in turn, transitioned to the (M)‐chirality according to the Z‐helicity of the DNA. These results illustrate the chirality synchronization between the DNA and the ligand.
Let′s twist again! The 2,13‐dimethoxy[5]helicene–spermine ligand 8 b possesses an axial chirality. The racemic 8 b was bound to B‐DNA with accompanying induction of its (P)‐chirality together with the B‐to‐Z helicity change of the duplex DNA, [(dC‐dG)3]2. The (P)‐chirality of the bound 8 b, in turn, transitioned to the (M)‐chirality according to the Z‐helicity of DNA. These results have illustrated the chirality synchronization between the DNA and ligand.</description><subject>B–Z transition</subject><subject>Chemistry</subject><subject>Chirality</subject><subject>Circular Dichroism</subject><subject>Deoxyribonucleic acid</subject><subject>DNA</subject><subject>DNA, B-Form - chemistry</subject><subject>DNA, B-Form - metabolism</subject><subject>DNA, Z-Form - chemistry</subject><subject>DNA, Z-Form - metabolism</subject><subject>helicene</subject><subject>Helicity</subject><subject>Ligands</subject><subject>Molecular Conformation</subject><subject>Nucleic Acid Conformation</subject><subject>Polycyclic Compounds - chemistry</subject><subject>Polycyclic Compounds - metabolism</subject><subject>Spermine - chemistry</subject><subject>Spermine - metabolism</subject><subject>Stereoisomerism</subject><subject>Synchronism</subject><subject>Synchronization</subject><subject>Thermodynamics</subject><issn>0947-6539</issn><issn>1521-3765</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2017</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqN0c1uEzEUBWALUdHQsmWJRmLTzaTX__ayhJZUSmHRrApo5PF4iKsZT7AzqsKKd-ANeZI6SikSG7qwLF1998jWQeg1hikGIKd25fopASyAEymeoQnmBJdUCv4cTUAzWQpO9SF6mdItAGhB6Qt0SKRmlCk8QV-ut8Gu4hD8D9cUs5WPpisuQzPajR9CUbvNnXOh-My_zl3nrQvu989f12sXex9csfDfTGiK3XmX5zfF-49nxTKakPxu_RgdtKZL7tXDfYSWF-fL2bxcfPpwOTtblJYzIspaCdEwabUCzqjATADDRrREtBYam59NG2h1m-eYMJkndWu0BjCyxkTRI3Syj13H4fvo0qbqfbKu60xww5gqrBTDlFMmnkAlUVhxjZ9AORGCAINM3_5Db4cxhvzlrAQnVElNsprulY1DStG11Tr63sRthaHalVntyqwey8wLbx5ix7p3zSP_014Geg_ufOe2_4mrZvPzq7_h92mAqes</recordid><startdate>20170203</startdate><enddate>20170203</enddate><creator>Kawara, Kensuke</creator><creator>Tsuji, Genichiro</creator><creator>Taniguchi, Yosuke</creator><creator>Sasaki, Shigeki</creator><general>Wiley Subscription Services, Inc</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>7SR</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope><scope>K9.</scope><scope>7X8</scope><scope>7TM</scope><orcidid>https://orcid.org/0000-0002-8985-3629</orcidid><orcidid>https://orcid.org/0000-0003-2013-2441</orcidid></search><sort><creationdate>20170203</creationdate><title>Synchronized Chiral Induction between [5]Helicene–Spermine Ligand and B–Z DNA Transition</title><author>Kawara, Kensuke ; Tsuji, Genichiro ; Taniguchi, Yosuke ; Sasaki, Shigeki</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c5426-b866d47c9805436146041a6f26fc0dc0003d0f9f4601247dc0bfa9900a7b1283</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2017</creationdate><topic>B–Z transition</topic><topic>Chemistry</topic><topic>Chirality</topic><topic>Circular Dichroism</topic><topic>Deoxyribonucleic acid</topic><topic>DNA</topic><topic>DNA, B-Form - chemistry</topic><topic>DNA, B-Form - metabolism</topic><topic>DNA, Z-Form - chemistry</topic><topic>DNA, Z-Form - metabolism</topic><topic>helicene</topic><topic>Helicity</topic><topic>Ligands</topic><topic>Molecular Conformation</topic><topic>Nucleic Acid Conformation</topic><topic>Polycyclic Compounds - chemistry</topic><topic>Polycyclic Compounds - metabolism</topic><topic>Spermine - chemistry</topic><topic>Spermine - metabolism</topic><topic>Stereoisomerism</topic><topic>Synchronism</topic><topic>Synchronization</topic><topic>Thermodynamics</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Kawara, Kensuke</creatorcontrib><creatorcontrib>Tsuji, Genichiro</creatorcontrib><creatorcontrib>Taniguchi, Yosuke</creatorcontrib><creatorcontrib>Sasaki, Shigeki</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>Engineered Materials Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><collection>ProQuest Health & Medical Complete (Alumni)</collection><collection>MEDLINE - Academic</collection><collection>Nucleic Acids Abstracts</collection><jtitle>Chemistry : a European journal</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Kawara, Kensuke</au><au>Tsuji, Genichiro</au><au>Taniguchi, Yosuke</au><au>Sasaki, Shigeki</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synchronized Chiral Induction between [5]Helicene–Spermine Ligand and B–Z DNA Transition</atitle><jtitle>Chemistry : a European journal</jtitle><addtitle>Chemistry</addtitle><date>2017-02-03</date><risdate>2017</risdate><volume>23</volume><issue>8</issue><spage>1763</spage><epage>1769</epage><pages>1763-1769</pages><issn>0947-6539</issn><eissn>1521-3765</eissn><coden>CEUJED</coden><abstract>The 2,13‐dimethoxy[5]helicene–spermine ligand 8 b possesses an axial chirality. The racemic 8 b was bound to B‐DNA by the accompanying induction of its (P)‐chirality together with the B‐to‐Z helicity change of the duplex DNA, [(dC‐dG)3]2. The (P)‐chirality of the bound 8 b, in turn, transitioned to the (M)‐chirality according to the Z‐helicity of the DNA. These results illustrate the chirality synchronization between the DNA and the ligand.
Let′s twist again! The 2,13‐dimethoxy[5]helicene–spermine ligand 8 b possesses an axial chirality. The racemic 8 b was bound to B‐DNA with accompanying induction of its (P)‐chirality together with the B‐to‐Z helicity change of the duplex DNA, [(dC‐dG)3]2. The (P)‐chirality of the bound 8 b, in turn, transitioned to the (M)‐chirality according to the Z‐helicity of DNA. These results have illustrated the chirality synchronization between the DNA and ligand.</abstract><cop>Germany</cop><pub>Wiley Subscription Services, Inc</pub><pmid>27943481</pmid><doi>10.1002/chem.201605276</doi><tpages>7</tpages><orcidid>https://orcid.org/0000-0002-8985-3629</orcidid><orcidid>https://orcid.org/0000-0003-2013-2441</orcidid></addata></record> |
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| subjects | B–Z transition Chemistry Chirality Circular Dichroism Deoxyribonucleic acid DNA DNA, B-Form - chemistry DNA, B-Form - metabolism DNA, Z-Form - chemistry DNA, Z-Form - metabolism helicene Helicity Ligands Molecular Conformation Nucleic Acid Conformation Polycyclic Compounds - chemistry Polycyclic Compounds - metabolism Spermine - chemistry Spermine - metabolism Stereoisomerism Synchronism Synchronization Thermodynamics |
| title | Synchronized Chiral Induction between [5]Helicene–Spermine Ligand and B–Z DNA Transition |
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