2,6‐Dimercuriphenol as a Bifacial Dinuclear Organometallic Nucleobase
A C‐nucleoside having 2,6‐dimercuriphenol as the base moiety has been synthesized and incorporated into an oligonucleotide. NMR and UV melting experiments revealed the ability of this bifacial organometallic nucleobase surrogate to form stable dinuclear HgII‐mediated base triples with adenine, cytos...
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| Veröffentlicht in: | Angewandte Chemie International Edition 2018-12, Vol.57 (49), p.16171-16175 |
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| creator | Ukale, Dattatraya Uttam Lönnberg, Tuomas |
| description | A C‐nucleoside having 2,6‐dimercuriphenol as the base moiety has been synthesized and incorporated into an oligonucleotide. NMR and UV melting experiments revealed the ability of this bifacial organometallic nucleobase surrogate to form stable dinuclear HgII‐mediated base triples with adenine, cytosine, and thymine (or uracil) in solution as well as within a triple‐helical oligonucleotide. A single HgII‐mediated base triple between 2,6‐dimercuriphenol and two thymines increased both Hoogsteen and Watson–Crick melting temperatures of a 15‐mer pyrimidine⋅purine*pyrimidine triple helix by more than 10 °C relative to an unmodified triple helix of the same length. This novel binding mode could be exploited in targeting certain pathogenic nucleic acids as well as in DNA nanotechnology.
2,6‐Dimercuriphenol acts as a bifacial organometallic nucleobase, forming dinuclear HgII‐mediated base triples in solution as well as within a triple‐helical oligonucleotide. A single HgII‐mediated triple between 2,6‐dimercuriphenol and two thymines promoted both Hoogsteen and Watson–Crick hybridization of a 15‐mer pyrimidine⋅purine*pyrimidine triple helix by more than 10 °C. |
| doi_str_mv | 10.1002/anie.201809398 |
| format | Article |
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2,6‐Dimercuriphenol acts as a bifacial organometallic nucleobase, forming dinuclear HgII‐mediated base triples in solution as well as within a triple‐helical oligonucleotide. A single HgII‐mediated triple between 2,6‐dimercuriphenol and two thymines promoted both Hoogsteen and Watson–Crick hybridization of a 15‐mer pyrimidine⋅purine*pyrimidine triple helix by more than 10 °C.</description><edition>International ed. in English</edition><identifier>ISSN: 1433-7851</identifier><identifier>EISSN: 1521-3773</identifier><identifier>DOI: 10.1002/anie.201809398</identifier><identifier>PMID: 30358071</identifier><language>eng</language><publisher>Germany: Wiley Subscription Services, Inc</publisher><subject>Adenine ; base triple ; Cytosine ; Deoxyribonucleic acid ; DNA ; hybridization ; Melting ; mercury ; Nanotechnology ; NMR ; Nuclear magnetic resonance ; Nucleic acids ; nucleobases ; Oligonucleotides ; Thymine ; Uracil</subject><ispartof>Angewandte Chemie International Edition, 2018-12, Vol.57 (49), p.16171-16175</ispartof><rights>2018 Wiley‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><rights>2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c4768-98633a567d9e3bce9f4114578ffaadc91f077071b625c6eaa3b5c5b26745ddaa3</citedby><cites>FETCH-LOGICAL-c4768-98633a567d9e3bce9f4114578ffaadc91f077071b625c6eaa3b5c5b26745ddaa3</cites><orcidid>0000-0003-3607-3116</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%2Fanie.201809398$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fanie.201809398$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,780,784,1417,27924,27925,45574,45575</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/30358071$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Ukale, Dattatraya Uttam</creatorcontrib><creatorcontrib>Lönnberg, Tuomas</creatorcontrib><title>2,6‐Dimercuriphenol as a Bifacial Dinuclear Organometallic Nucleobase</title><title>Angewandte Chemie International Edition</title><addtitle>Angew Chem Int Ed Engl</addtitle><description>A C‐nucleoside having 2,6‐dimercuriphenol as the base moiety has been synthesized and incorporated into an oligonucleotide. NMR and UV melting experiments revealed the ability of this bifacial organometallic nucleobase surrogate to form stable dinuclear HgII‐mediated base triples with adenine, cytosine, and thymine (or uracil) in solution as well as within a triple‐helical oligonucleotide. A single HgII‐mediated base triple between 2,6‐dimercuriphenol and two thymines increased both Hoogsteen and Watson–Crick melting temperatures of a 15‐mer pyrimidine⋅purine*pyrimidine triple helix by more than 10 °C relative to an unmodified triple helix of the same length. This novel binding mode could be exploited in targeting certain pathogenic nucleic acids as well as in DNA nanotechnology.
2,6‐Dimercuriphenol acts as a bifacial organometallic nucleobase, forming dinuclear HgII‐mediated base triples in solution as well as within a triple‐helical oligonucleotide. A single HgII‐mediated triple between 2,6‐dimercuriphenol and two thymines promoted both Hoogsteen and Watson–Crick hybridization of a 15‐mer pyrimidine⋅purine*pyrimidine triple helix by more than 10 °C.</description><subject>Adenine</subject><subject>base triple</subject><subject>Cytosine</subject><subject>Deoxyribonucleic acid</subject><subject>DNA</subject><subject>hybridization</subject><subject>Melting</subject><subject>mercury</subject><subject>Nanotechnology</subject><subject>NMR</subject><subject>Nuclear magnetic resonance</subject><subject>Nucleic acids</subject><subject>nucleobases</subject><subject>Oligonucleotides</subject><subject>Thymine</subject><subject>Uracil</subject><issn>1433-7851</issn><issn>1521-3773</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2018</creationdate><recordtype>article</recordtype><recordid>eNqF0LtOwzAUBmALgaAUVkYUiYWBFF_i2B4LLaVSBQvM0YnjgJGTFLsRYuMReEaeBFflIrEw2T76_OvoR-iI4BHBmJ5Da82IYiKxYkpuoQHhlKRMCLYd7xljqZCc7KH9EJ6ilxLnu2iPYcYlFmSAZvQs_3h7n9jGeN17u3w0becSCAkkF7YGbcElE9v22hnwya1_gLZrzAqcszq5WY-7EoI5QDs1uGAOv84hur-a3l1ep4vb2fxyvEh1JnKZKpkzBjwXlTKs1EbVGSEZF7KuASqtSI2FiIuVOeU6NwCs5JqXNBcZr6r4HKLTTe7Sd8-9CauisUEb56A1XR8KSiinSmSKR3ryhz51vW_jdlExkTGJKY5qtFHadyF4UxdLbxvwrwXBxbriYl1x8VNx_HD8FduXjal--HenEagNeLHOvP4TV4xv5tPf8E-nmYef</recordid><startdate>20181203</startdate><enddate>20181203</enddate><creator>Ukale, Dattatraya Uttam</creator><creator>Lönnberg, Tuomas</creator><general>Wiley Subscription Services, Inc</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7TM</scope><scope>K9.</scope><scope>7X8</scope><orcidid>https://orcid.org/0000-0003-3607-3116</orcidid></search><sort><creationdate>20181203</creationdate><title>2,6‐Dimercuriphenol as a Bifacial Dinuclear Organometallic Nucleobase</title><author>Ukale, Dattatraya Uttam ; Lönnberg, Tuomas</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c4768-98633a567d9e3bce9f4114578ffaadc91f077071b625c6eaa3b5c5b26745ddaa3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2018</creationdate><topic>Adenine</topic><topic>base triple</topic><topic>Cytosine</topic><topic>Deoxyribonucleic acid</topic><topic>DNA</topic><topic>hybridization</topic><topic>Melting</topic><topic>mercury</topic><topic>Nanotechnology</topic><topic>NMR</topic><topic>Nuclear magnetic resonance</topic><topic>Nucleic acids</topic><topic>nucleobases</topic><topic>Oligonucleotides</topic><topic>Thymine</topic><topic>Uracil</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Ukale, Dattatraya Uttam</creatorcontrib><creatorcontrib>Lönnberg, Tuomas</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><collection>Nucleic Acids Abstracts</collection><collection>ProQuest Health & Medical Complete (Alumni)</collection><collection>MEDLINE - Academic</collection><jtitle>Angewandte Chemie International Edition</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Ukale, Dattatraya Uttam</au><au>Lönnberg, Tuomas</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>2,6‐Dimercuriphenol as a Bifacial Dinuclear Organometallic Nucleobase</atitle><jtitle>Angewandte Chemie International Edition</jtitle><addtitle>Angew Chem Int Ed Engl</addtitle><date>2018-12-03</date><risdate>2018</risdate><volume>57</volume><issue>49</issue><spage>16171</spage><epage>16175</epage><pages>16171-16175</pages><issn>1433-7851</issn><eissn>1521-3773</eissn><abstract>A C‐nucleoside having 2,6‐dimercuriphenol as the base moiety has been synthesized and incorporated into an oligonucleotide. NMR and UV melting experiments revealed the ability of this bifacial organometallic nucleobase surrogate to form stable dinuclear HgII‐mediated base triples with adenine, cytosine, and thymine (or uracil) in solution as well as within a triple‐helical oligonucleotide. A single HgII‐mediated base triple between 2,6‐dimercuriphenol and two thymines increased both Hoogsteen and Watson–Crick melting temperatures of a 15‐mer pyrimidine⋅purine*pyrimidine triple helix by more than 10 °C relative to an unmodified triple helix of the same length. This novel binding mode could be exploited in targeting certain pathogenic nucleic acids as well as in DNA nanotechnology.
2,6‐Dimercuriphenol acts as a bifacial organometallic nucleobase, forming dinuclear HgII‐mediated base triples in solution as well as within a triple‐helical oligonucleotide. A single HgII‐mediated triple between 2,6‐dimercuriphenol and two thymines promoted both Hoogsteen and Watson–Crick hybridization of a 15‐mer pyrimidine⋅purine*pyrimidine triple helix by more than 10 °C.</abstract><cop>Germany</cop><pub>Wiley Subscription Services, Inc</pub><pmid>30358071</pmid><doi>10.1002/anie.201809398</doi><tpages>5</tpages><edition>International ed. in English</edition><orcidid>https://orcid.org/0000-0003-3607-3116</orcidid></addata></record> |
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| subjects | Adenine base triple Cytosine Deoxyribonucleic acid DNA hybridization Melting mercury Nanotechnology NMR Nuclear magnetic resonance Nucleic acids nucleobases Oligonucleotides Thymine Uracil |
| title | 2,6‐Dimercuriphenol as a Bifacial Dinuclear Organometallic Nucleobase |
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