Nonenzymatic Synthesis of RNA and DNA Oligomers on Hexitol Nucleic Acid Templates: The Importance of the A Structure
Hexitol nucleic acid (HNA) is an analogue of DNA containing the standard nucleoside bases, but with a phosphorylated 1,5-anhydrohexitol backbone. HNA oligomers form duplexes having the nucleic acid A structure with complementary DNA or RNA oligomers. The HNA decacytidylate oligomer is an efficient t...
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| Veröffentlicht in: | Journal of the American Chemical Society 1999-03, Vol.121 (12), p.2653-2656 |
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| container_issue | 12 |
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| container_title | Journal of the American Chemical Society |
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| creator | Kozlov, Igor A Politis, Panagiotis K Van Aerschot, Arthur Busson, Roger Herdewijn, Piet Orgel, Leslie E |
| description | Hexitol nucleic acid (HNA) is an analogue of DNA containing the standard nucleoside bases, but with a phosphorylated 1,5-anhydrohexitol backbone. HNA oligomers form duplexes having the nucleic acid A structure with complementary DNA or RNA oligomers. The HNA decacytidylate oligomer is an efficient template for the oligomerization of the 5‘-phosphoroimidazolides of guanosine or deoxyguanosine. Comparison of the oligomerization efficiencies on HNA, RNA, and DNA decacytidylate templates under various conditions suggests strongly that only nucleic acid double helices with the A structure support efficient template-directed synthesis when 5‘-phosphoroimidazolides of nucleosides are used as substrates. |
| doi_str_mv | 10.1021/ja983958r |
| format | Article |
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HNA oligomers form duplexes having the nucleic acid A structure with complementary DNA or RNA oligomers. The HNA decacytidylate oligomer is an efficient template for the oligomerization of the 5‘-phosphoroimidazolides of guanosine or deoxyguanosine. Comparison of the oligomerization efficiencies on HNA, RNA, and DNA decacytidylate templates under various conditions suggests strongly that only nucleic acid double helices with the A structure support efficient template-directed synthesis when 5‘-phosphoroimidazolides of nucleosides are used as substrates.</description><identifier>ISSN: 0002-7863</identifier><identifier>EISSN: 1520-5126</identifier><identifier>DOI: 10.1021/ja983958r</identifier><identifier>PMID: 11543583</identifier><language>eng</language><publisher>Goddard Space Flight Center: American Chemical Society</publisher><subject>1,5-anhydrohexitol ; Catalysis ; deoxyguanosine ; DNA - chemistry ; Exobiology ; guanosine ; Guanosine Monophosphate - analogs & derivatives ; Guanosine Monophosphate - chemistry ; Hexitol nucleic acids ; Lead ; Molecular Structure ; Oligonucleotides - chemical synthesis ; RNA - chemistry ; Space life sciences ; Sugar Alcohols - chemistry ; Templates, Genetic</subject><ispartof>Journal of the American Chemical Society, 1999-03, Vol.121 (12), p.2653-2656</ispartof><rights>Copyright © 1999 American Chemical Society</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a498t-d0b3320f36845fc16c9174061413640b5e38fdbba062ac62780e5f318300e7893</citedby><cites>FETCH-LOGICAL-a498t-d0b3320f36845fc16c9174061413640b5e38fdbba062ac62780e5f318300e7893</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/ja983958r$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/ja983958r$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,780,784,2765,27076,27924,27925,56738,56788</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/11543583$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Kozlov, Igor A</creatorcontrib><creatorcontrib>Politis, Panagiotis K</creatorcontrib><creatorcontrib>Van Aerschot, Arthur</creatorcontrib><creatorcontrib>Busson, Roger</creatorcontrib><creatorcontrib>Herdewijn, Piet</creatorcontrib><creatorcontrib>Orgel, Leslie E</creatorcontrib><title>Nonenzymatic Synthesis of RNA and DNA Oligomers on Hexitol Nucleic Acid Templates: The Importance of the A Structure</title><title>Journal of the American Chemical Society</title><addtitle>J. Am. Chem. Soc</addtitle><description>Hexitol nucleic acid (HNA) is an analogue of DNA containing the standard nucleoside bases, but with a phosphorylated 1,5-anhydrohexitol backbone. HNA oligomers form duplexes having the nucleic acid A structure with complementary DNA or RNA oligomers. The HNA decacytidylate oligomer is an efficient template for the oligomerization of the 5‘-phosphoroimidazolides of guanosine or deoxyguanosine. Comparison of the oligomerization efficiencies on HNA, RNA, and DNA decacytidylate templates under various conditions suggests strongly that only nucleic acid double helices with the A structure support efficient template-directed synthesis when 5‘-phosphoroimidazolides of nucleosides are used as substrates.</description><subject>1,5-anhydrohexitol</subject><subject>Catalysis</subject><subject>deoxyguanosine</subject><subject>DNA - chemistry</subject><subject>Exobiology</subject><subject>guanosine</subject><subject>Guanosine Monophosphate - analogs & derivatives</subject><subject>Guanosine Monophosphate - chemistry</subject><subject>Hexitol nucleic acids</subject><subject>Lead</subject><subject>Molecular Structure</subject><subject>Oligonucleotides - chemical synthesis</subject><subject>RNA - chemistry</subject><subject>Space life sciences</subject><subject>Sugar Alcohols - chemistry</subject><subject>Templates, Genetic</subject><issn>0002-7863</issn><issn>1520-5126</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>1999</creationdate><recordtype>article</recordtype><sourceid>CYI</sourceid><sourceid>EIF</sourceid><recordid>eNqNkU9v1DAQxS0EokvhwB0hX0DiEPD_OL2tWqBFqy1iF3G0HO-EZkmcxXZElxNXviafBFdZlQsSnEaj95s3M3oIPabkJSWMvtraSvNK6nAHzahkpJCUqbtoRghhRakVP0IPYtzmVjBN76MjSqXgUvMZ-rYcPPjv-96m1uHV3qcriG3EQ4M_LOfY-g0-y_Wyaz8PPYQseHwO120aOrwcXQd5au7aDV5Dv-tsgnjy68dPvL4CfNHvhpCsd3Djln3xHK9SGF0aAzxE9xrbRXh0qMfo45vX69PzYnH59uJ0viisqHQqNqTmnJGGKy1k46hyFS0FUVRQrgSpJXDdbOraEsWsU6zUBGTDqeaEQKkrfoyeT767MHwdISbTt9FB11kPwxiNqvIeVfJ_gnmtokzS_wGFEkxk8MUEujDEGKAxu9D2NuwNJeYmN3ObW2afHkzHuofNH_IQVAaeTIC30RqfQjQsx0mI1mUls1xMchsTXN-O2_DF5OdKadbvV4Yu-PKd-CTNWeafTbx10WyHMfgcwl_u-g3oNLUZ</recordid><startdate>19990331</startdate><enddate>19990331</enddate><creator>Kozlov, Igor A</creator><creator>Politis, Panagiotis K</creator><creator>Van Aerschot, Arthur</creator><creator>Busson, Roger</creator><creator>Herdewijn, Piet</creator><creator>Orgel, Leslie E</creator><general>American Chemical Society</general><scope>BSCLL</scope><scope>CYE</scope><scope>CYI</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>7TM</scope><scope>7X8</scope></search><sort><creationdate>19990331</creationdate><title>Nonenzymatic Synthesis of RNA and DNA Oligomers on Hexitol Nucleic Acid Templates: The Importance of the A Structure</title><author>Kozlov, Igor A ; Politis, Panagiotis K ; Van Aerschot, Arthur ; Busson, Roger ; Herdewijn, Piet ; Orgel, Leslie E</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a498t-d0b3320f36845fc16c9174061413640b5e38fdbba062ac62780e5f318300e7893</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>1999</creationdate><topic>1,5-anhydrohexitol</topic><topic>Catalysis</topic><topic>deoxyguanosine</topic><topic>DNA - chemistry</topic><topic>Exobiology</topic><topic>guanosine</topic><topic>Guanosine Monophosphate - analogs & derivatives</topic><topic>Guanosine Monophosphate - chemistry</topic><topic>Hexitol nucleic acids</topic><topic>Lead</topic><topic>Molecular Structure</topic><topic>Oligonucleotides - chemical synthesis</topic><topic>RNA - chemistry</topic><topic>Space life sciences</topic><topic>Sugar Alcohols - chemistry</topic><topic>Templates, Genetic</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Kozlov, Igor A</creatorcontrib><creatorcontrib>Politis, Panagiotis K</creatorcontrib><creatorcontrib>Van Aerschot, Arthur</creatorcontrib><creatorcontrib>Busson, Roger</creatorcontrib><creatorcontrib>Herdewijn, Piet</creatorcontrib><creatorcontrib>Orgel, Leslie E</creatorcontrib><collection>Istex</collection><collection>NASA Scientific and Technical Information</collection><collection>NASA Technical Reports Server</collection><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>Nucleic Acids Abstracts</collection><collection>MEDLINE - Academic</collection><jtitle>Journal of the American Chemical Society</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Kozlov, Igor A</au><au>Politis, Panagiotis K</au><au>Van Aerschot, Arthur</au><au>Busson, Roger</au><au>Herdewijn, Piet</au><au>Orgel, Leslie E</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Nonenzymatic Synthesis of RNA and DNA Oligomers on Hexitol Nucleic Acid Templates: The Importance of the A Structure</atitle><jtitle>Journal of the American Chemical Society</jtitle><addtitle>J. Am. Chem. Soc</addtitle><date>1999-03-31</date><risdate>1999</risdate><volume>121</volume><issue>12</issue><spage>2653</spage><epage>2656</epage><pages>2653-2656</pages><issn>0002-7863</issn><eissn>1520-5126</eissn><abstract>Hexitol nucleic acid (HNA) is an analogue of DNA containing the standard nucleoside bases, but with a phosphorylated 1,5-anhydrohexitol backbone. HNA oligomers form duplexes having the nucleic acid A structure with complementary DNA or RNA oligomers. The HNA decacytidylate oligomer is an efficient template for the oligomerization of the 5‘-phosphoroimidazolides of guanosine or deoxyguanosine. Comparison of the oligomerization efficiencies on HNA, RNA, and DNA decacytidylate templates under various conditions suggests strongly that only nucleic acid double helices with the A structure support efficient template-directed synthesis when 5‘-phosphoroimidazolides of nucleosides are used as substrates.</abstract><cop>Goddard Space Flight Center</cop><pub>American Chemical Society</pub><pmid>11543583</pmid><doi>10.1021/ja983958r</doi><tpages>4</tpages></addata></record> |
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| ispartof | Journal of the American Chemical Society, 1999-03, Vol.121 (12), p.2653-2656 |
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| source | MEDLINE; NASA Technical Reports Server; American Chemical Society Journals |
| subjects | 1,5-anhydrohexitol Catalysis deoxyguanosine DNA - chemistry Exobiology guanosine Guanosine Monophosphate - analogs & derivatives Guanosine Monophosphate - chemistry Hexitol nucleic acids Lead Molecular Structure Oligonucleotides - chemical synthesis RNA - chemistry Space life sciences Sugar Alcohols - chemistry Templates, Genetic |
| title | Nonenzymatic Synthesis of RNA and DNA Oligomers on Hexitol Nucleic Acid Templates: The Importance of the A Structure |
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