Stabilization of tandem dG-dA base pairs in DNA-hairpins: replacement of the canonical bases by 7-deaza-7-propynylpurines
The stabilizing effect of 7-propynylated 7-deazapurine nucleosides on DNA-hairpins and DNA-duplexes containing d(GA) mismatches was investigated. The corresponding oligonucleotides were synthesized using solid-phase synthesis. For this purpose, the phosphoramidite of 7-deaza-7-propynyl-2'-deoxy...
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| Veröffentlicht in: | Organic & biomolecular chemistry 2005-12, Vol.3 (23), p.4221-4226 |
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| container_title | Organic & biomolecular chemistry |
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| creator | Seela, Frank Budow, Simone Shaikh, Khalil I Jawalekar, Anup M |
| description | The stabilizing effect of 7-propynylated 7-deazapurine nucleosides on DNA-hairpins and DNA-duplexes containing d(GA) mismatches was investigated. The corresponding oligonucleotides were synthesized using solid-phase synthesis. For this purpose, the phosphoramidite of 7-deaza-7-propynyl-2'-deoxyadenosine (3c) was prepared. The incorporation of 3c instead of dA into the tandem d(GA) base pair of a DNA-hairpin alters the secondary structure, but has a positive effect on the duplex stability. A complete replacement of the canonical nucleosides of the tandem d(GA) base pair by 3c and 7-deaza-7-propynyl-2'-deoxyguanosine results in a significant base pair stabilization. |
| doi_str_mv | 10.1039/b510444k |
| format | Article |
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The corresponding oligonucleotides were synthesized using solid-phase synthesis. For this purpose, the phosphoramidite of 7-deaza-7-propynyl-2'-deoxyadenosine (3c) was prepared. The incorporation of 3c instead of dA into the tandem d(GA) base pair of a DNA-hairpin alters the secondary structure, but has a positive effect on the duplex stability. 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The corresponding oligonucleotides were synthesized using solid-phase synthesis. For this purpose, the phosphoramidite of 7-deaza-7-propynyl-2'-deoxyadenosine (3c) was prepared. The incorporation of 3c instead of dA into the tandem d(GA) base pair of a DNA-hairpin alters the secondary structure, but has a positive effect on the duplex stability. A complete replacement of the canonical nucleosides of the tandem d(GA) base pair by 3c and 7-deaza-7-propynyl-2'-deoxyguanosine results in a significant base pair stabilization.</description><subject>Base Pairing</subject><subject>Base Sequence</subject><subject>Circular Dichroism</subject><subject>Deoxyadenosines - chemistry</subject><subject>Deoxyguanosine - analogs & derivatives</subject><subject>Deoxyguanosine - chemistry</subject><subject>Nucleic Acid Conformation</subject><subject>Thermodynamics</subject><issn>1477-0520</issn><issn>1477-0539</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2005</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNpFkLFOwzAQhi0EoqUg8QTIE2Ix2I6TOGxVgYJUwQDMkWOfVUPihDgZ0qcntAWmu5O-_z_pQ-ic0WtGo-ymiBkVQnweoCkTaUpoHGWHfzunE3QSwgelLEsTcYwmLOGZ4DGdouG1U4Ur3UZ1rva4trhT3kCFzZKYOS5UANwo1wbsPL57npP1eDTOh1vcQlMqDRX4bptbA9bK195pVW6DARcDTokBtVEkJU1bN4MfyqZvnYdwio6sKgOc7ecMvT_cvy0eyepl-bSYr4jmknWEiaRIQVINUapYxriVlkUstVYk3MYWgBkjYiFlkWltZcSyRBrLk9gmJlIqmqHLXe_4_6uH0OWVCxrKUnmo-5AnUjLOqRjBqx2o2zqEFmzetK5S7ZAzmv9ozn81j-jFvrMvKjD_4N5r9A0Zd3hE</recordid><startdate>20051207</startdate><enddate>20051207</enddate><creator>Seela, Frank</creator><creator>Budow, Simone</creator><creator>Shaikh, Khalil I</creator><creator>Jawalekar, Anup M</creator><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>7X8</scope></search><sort><creationdate>20051207</creationdate><title>Stabilization of tandem dG-dA base pairs in DNA-hairpins: replacement of the canonical bases by 7-deaza-7-propynylpurines</title><author>Seela, Frank ; Budow, Simone ; Shaikh, Khalil I ; Jawalekar, Anup M</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c281t-146b7e80ce37a1912f8f1317ff462f5fee1dd45488b9ccf831968df265f6d3aa3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2005</creationdate><topic>Base Pairing</topic><topic>Base Sequence</topic><topic>Circular Dichroism</topic><topic>Deoxyadenosines - chemistry</topic><topic>Deoxyguanosine - analogs & derivatives</topic><topic>Deoxyguanosine - chemistry</topic><topic>Nucleic Acid Conformation</topic><topic>Thermodynamics</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Seela, Frank</creatorcontrib><creatorcontrib>Budow, Simone</creatorcontrib><creatorcontrib>Shaikh, Khalil I</creatorcontrib><creatorcontrib>Jawalekar, Anup M</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Organic & biomolecular chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Seela, Frank</au><au>Budow, Simone</au><au>Shaikh, Khalil I</au><au>Jawalekar, Anup M</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Stabilization of tandem dG-dA base pairs in DNA-hairpins: replacement of the canonical bases by 7-deaza-7-propynylpurines</atitle><jtitle>Organic & biomolecular chemistry</jtitle><addtitle>Org Biomol Chem</addtitle><date>2005-12-07</date><risdate>2005</risdate><volume>3</volume><issue>23</issue><spage>4221</spage><epage>4226</epage><pages>4221-4226</pages><issn>1477-0520</issn><eissn>1477-0539</eissn><abstract>The stabilizing effect of 7-propynylated 7-deazapurine nucleosides on DNA-hairpins and DNA-duplexes containing d(GA) mismatches was investigated. The corresponding oligonucleotides were synthesized using solid-phase synthesis. For this purpose, the phosphoramidite of 7-deaza-7-propynyl-2'-deoxyadenosine (3c) was prepared. The incorporation of 3c instead of dA into the tandem d(GA) base pair of a DNA-hairpin alters the secondary structure, but has a positive effect on the duplex stability. A complete replacement of the canonical nucleosides of the tandem d(GA) base pair by 3c and 7-deaza-7-propynyl-2'-deoxyguanosine results in a significant base pair stabilization.</abstract><cop>England</cop><pmid>16294250</pmid><doi>10.1039/b510444k</doi><tpages>6</tpages></addata></record> |
| fulltext | fulltext |
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| ispartof | Organic & biomolecular chemistry, 2005-12, Vol.3 (23), p.4221-4226 |
| issn | 1477-0520 1477-0539 |
| language | eng |
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| source | MEDLINE; Royal Society of Chemistry Journals Archive (1841-2007); Royal Society Of Chemistry Journals 2008-; Alma/SFX Local Collection |
| subjects | Base Pairing Base Sequence Circular Dichroism Deoxyadenosines - chemistry Deoxyguanosine - analogs & derivatives Deoxyguanosine - chemistry Nucleic Acid Conformation Thermodynamics |
| title | Stabilization of tandem dG-dA base pairs in DNA-hairpins: replacement of the canonical bases by 7-deaza-7-propynylpurines |
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