Oligonucleotides containing a covalent conformationally restricted phosphodiester analog for high-affinity triple helix formation: the riboacetal internucleotide linkage
The high-affinity, sequence-specific recognition of duplex (ds) DNA is an area of biological and chemical interest. Oligonucleotides (ONs) have been shown to recognize polypurine tracts of dsDNA in a sequence-specific manner via triple helix formation. Optimization of this ligand (ON)-receptor (dsDN...
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| Veröffentlicht in: | Journal of the American Chemical Society 1993-10, Vol.115 (21), p.9816-9817 |
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| container_end_page | 9817 |
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| container_issue | 21 |
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| container_title | Journal of the American Chemical Society |
| container_volume | 115 |
| creator | Jones, Robert J Swaminathan, S Milligan, John F Wadwani, Shalini Froehler, Brian C Matteucci, Mark D |
| description | The high-affinity, sequence-specific recognition of duplex (ds) DNA is an area of biological and chemical interest. Oligonucleotides (ONs) have been shown to recognize polypurine tracts of dsDNA in a sequence-specific manner via triple helix formation. Optimization of this ligand (ON)-receptor (dsDNA) interaction can be conceptually achieved by restricting the conformational freedom of unbound ON to resemble its bound conformation. The enhancement of ligand-receptor interactions through conformational restriction has been elegantly demonstrated in the field of crown ethers and cryptands and has been extended to ligands binding to hormone receptors and enzyme inhibitors. We report the application of this concept to the ON-dsDNA ligand-receptor interaction by replacing the phosphodiester internucleotide connection with a conformationally restricted acetal linkage which we have termed "riboacetal." |
| doi_str_mv | 10.1021/ja00074a065 |
| format | Article |
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Am. Chem. Soc</addtitle><description>The high-affinity, sequence-specific recognition of duplex (ds) DNA is an area of biological and chemical interest. Oligonucleotides (ONs) have been shown to recognize polypurine tracts of dsDNA in a sequence-specific manner via triple helix formation. Optimization of this ligand (ON)-receptor (dsDNA) interaction can be conceptually achieved by restricting the conformational freedom of unbound ON to resemble its bound conformation. The enhancement of ligand-receptor interactions through conformational restriction has been elegantly demonstrated in the field of crown ethers and cryptands and has been extended to ligands binding to hormone receptors and enzyme inhibitors. We report the application of this concept to the ON-dsDNA ligand-receptor interaction by replacing the phosphodiester internucleotide connection with a conformationally restricted acetal linkage which we have termed "riboacetal."</description><subject>Biological and medical sciences</subject><subject>Cell metabolism, cell oxidation</subject><subject>Cell physiology</subject><subject>Fundamental and applied biological sciences. 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Psychology</topic><topic>Molecular and cellular biology</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Jones, Robert J</creatorcontrib><creatorcontrib>Swaminathan, S</creatorcontrib><creatorcontrib>Milligan, John F</creatorcontrib><creatorcontrib>Wadwani, Shalini</creatorcontrib><creatorcontrib>Froehler, Brian C</creatorcontrib><creatorcontrib>Matteucci, Mark D</creatorcontrib><collection>Istex</collection><collection>Pascal-Francis</collection><collection>CrossRef</collection><collection>Nucleic Acids Abstracts</collection><jtitle>Journal of the American Chemical Society</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Jones, Robert J</au><au>Swaminathan, S</au><au>Milligan, John F</au><au>Wadwani, Shalini</au><au>Froehler, Brian C</au><au>Matteucci, Mark D</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Oligonucleotides containing a covalent conformationally restricted phosphodiester analog for high-affinity triple helix formation: the riboacetal internucleotide linkage</atitle><jtitle>Journal of the American Chemical Society</jtitle><addtitle>J. Am. Chem. Soc</addtitle><date>1993-10-01</date><risdate>1993</risdate><volume>115</volume><issue>21</issue><spage>9816</spage><epage>9817</epage><pages>9816-9817</pages><issn>0002-7863</issn><eissn>1520-5126</eissn><coden>JACSAT</coden><abstract>The high-affinity, sequence-specific recognition of duplex (ds) DNA is an area of biological and chemical interest. Oligonucleotides (ONs) have been shown to recognize polypurine tracts of dsDNA in a sequence-specific manner via triple helix formation. Optimization of this ligand (ON)-receptor (dsDNA) interaction can be conceptually achieved by restricting the conformational freedom of unbound ON to resemble its bound conformation. The enhancement of ligand-receptor interactions through conformational restriction has been elegantly demonstrated in the field of crown ethers and cryptands and has been extended to ligands binding to hormone receptors and enzyme inhibitors. We report the application of this concept to the ON-dsDNA ligand-receptor interaction by replacing the phosphodiester internucleotide connection with a conformationally restricted acetal linkage which we have termed "riboacetal."</abstract><cop>Washington, DC</cop><pub>American Chemical Society</pub><doi>10.1021/ja00074a065</doi><tpages>2</tpages></addata></record> |
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| identifier | ISSN: 0002-7863 |
| ispartof | Journal of the American Chemical Society, 1993-10, Vol.115 (21), p.9816-9817 |
| issn | 0002-7863 1520-5126 |
| language | eng |
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| source | American Chemical Society Journals |
| subjects | Biological and medical sciences Cell metabolism, cell oxidation Cell physiology Fundamental and applied biological sciences. Psychology Molecular and cellular biology |
| title | Oligonucleotides containing a covalent conformationally restricted phosphodiester analog for high-affinity triple helix formation: the riboacetal internucleotide linkage |
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