Characterization of high molecular weight impurities in synthetic phosphorothioate oligonucleotides
Phosphorothioate oligonucleotides manufactured by standard phosphoramidite techniques using nucleoside-loaded supports contain high molecular weight impurities of the type shown. These impurities are avoided if a novel universal solid support is used. Phosphorothioate oligonucleotides manufactured b...
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| Veröffentlicht in: | Bioorganic & medicinal chemistry letters 2006-02, Vol.16 (3), p.607-614 |
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| container_title | Bioorganic & medicinal chemistry letters |
| container_volume | 16 |
| creator | Kurata, Christine Bradley, Kym Gaus, Hans Luu, Nhuy Cedillo, Isaiah Ravikumar, Vasulinga T. Sooy, Kent Van McArdle, James V. Capaldi, Daniel C. |
| description | Phosphorothioate oligonucleotides manufactured by standard phosphoramidite techniques using nucleoside-loaded supports contain high molecular weight impurities of the type shown. These impurities are avoided if a novel universal solid support is used.
Phosphorothioate oligonucleotides manufactured by standard phosphoramidite techniques using 2′-deoxyadenosine- or 2′-
O-(2-methoxyethyl)-5-methylcytosine-loaded solid supports contain branched impurities consisting of two chains linked through the exocyclic amino group of the 3′-terminal nucleoside of one chain and the 3′-terminal hydroxyl group of another via a P(O)SH group. These impurities are not produced when a universal, non-nucleoside derivatized support is used. |
| doi_str_mv | 10.1016/j.bmcl.2005.10.051 |
| format | Article |
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Phosphorothioate oligonucleotides manufactured by standard phosphoramidite techniques using 2′-deoxyadenosine- or 2′-
O-(2-methoxyethyl)-5-methylcytosine-loaded solid supports contain branched impurities consisting of two chains linked through the exocyclic amino group of the 3′-terminal nucleoside of one chain and the 3′-terminal hydroxyl group of another via a P(O)SH group. These impurities are not produced when a universal, non-nucleoside derivatized support is used.</description><identifier>ISSN: 0960-894X</identifier><identifier>EISSN: 1464-3405</identifier><identifier>DOI: 10.1016/j.bmcl.2005.10.051</identifier><identifier>PMID: 16274991</identifier><language>eng</language><publisher>Oxford: Elsevier Ltd</publisher><subject>5-Methylcytosine - chemistry ; Analytical chemistry ; Carbohydrates. Nucleosides and nucleotides ; Chemistry ; Chromatographic methods and physical methods associated with chromatography ; Chromatography, High Pressure Liquid ; Deoxyadenosines - chemistry ; Exact sciences and technology ; Liquid chromatography–mass spectrometry ; Molecular Structure ; Molecular Weight ; Nucleosides, nucleotides and oligonucleotides ; Oligonucleotides - chemical synthesis ; Organic chemistry ; Organophosphorus Compounds - chemistry ; Other chromatographic methods ; Phosphorothioate oligonucleotides ; Preparations and properties ; Spectrophotometry, Ultraviolet ; Thionucleotides - chemistry ; Universal solid support</subject><ispartof>Bioorganic & medicinal chemistry letters, 2006-02, Vol.16 (3), p.607-614</ispartof><rights>2005 Elsevier Ltd</rights><rights>2006 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c384t-80f79b5b39038b231fdeaff6e75810be2b16867fc748bf1907d45b7cb57b1053</citedby><cites>FETCH-LOGICAL-c384t-80f79b5b39038b231fdeaff6e75810be2b16867fc748bf1907d45b7cb57b1053</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://www.sciencedirect.com/science/article/pii/S0960894X05013296$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,776,780,3537,27901,27902,65306</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=17391051$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/16274991$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Kurata, Christine</creatorcontrib><creatorcontrib>Bradley, Kym</creatorcontrib><creatorcontrib>Gaus, Hans</creatorcontrib><creatorcontrib>Luu, Nhuy</creatorcontrib><creatorcontrib>Cedillo, Isaiah</creatorcontrib><creatorcontrib>Ravikumar, Vasulinga T.</creatorcontrib><creatorcontrib>Sooy, Kent Van</creatorcontrib><creatorcontrib>McArdle, James V.</creatorcontrib><creatorcontrib>Capaldi, Daniel C.</creatorcontrib><title>Characterization of high molecular weight impurities in synthetic phosphorothioate oligonucleotides</title><title>Bioorganic & medicinal chemistry letters</title><addtitle>Bioorg Med Chem Lett</addtitle><description>Phosphorothioate oligonucleotides manufactured by standard phosphoramidite techniques using nucleoside-loaded supports contain high molecular weight impurities of the type shown. These impurities are avoided if a novel universal solid support is used.
Phosphorothioate oligonucleotides manufactured by standard phosphoramidite techniques using 2′-deoxyadenosine- or 2′-
O-(2-methoxyethyl)-5-methylcytosine-loaded solid supports contain branched impurities consisting of two chains linked through the exocyclic amino group of the 3′-terminal nucleoside of one chain and the 3′-terminal hydroxyl group of another via a P(O)SH group. These impurities are not produced when a universal, non-nucleoside derivatized support is used.</description><subject>5-Methylcytosine - chemistry</subject><subject>Analytical chemistry</subject><subject>Carbohydrates. Nucleosides and nucleotides</subject><subject>Chemistry</subject><subject>Chromatographic methods and physical methods associated with chromatography</subject><subject>Chromatography, High Pressure Liquid</subject><subject>Deoxyadenosines - chemistry</subject><subject>Exact sciences and technology</subject><subject>Liquid chromatography–mass spectrometry</subject><subject>Molecular Structure</subject><subject>Molecular Weight</subject><subject>Nucleosides, nucleotides and oligonucleotides</subject><subject>Oligonucleotides - chemical synthesis</subject><subject>Organic chemistry</subject><subject>Organophosphorus Compounds - chemistry</subject><subject>Other chromatographic methods</subject><subject>Phosphorothioate oligonucleotides</subject><subject>Preparations and properties</subject><subject>Spectrophotometry, Ultraviolet</subject><subject>Thionucleotides - chemistry</subject><subject>Universal solid support</subject><issn>0960-894X</issn><issn>1464-3405</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2006</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNp9kMFq3DAQhkVoaTZJXyCH4kt781ayZcuCXsrSNoVALzn0JiR5FM8iW1tJbkifPlp2IbcehmGGb36Gj5BbRreMsv7zfmtm67cNpV1ZbGnHLsiG8Z7XLafdG7Khsqf1IPnvS3KV0p5Sxinn78gl6xvBpWQbYneTjtpmiPhPZwxLFVw14eNUzcGDXb2O1ROUOVc4H9aIGSFVuFTpeckTZLTVYQqpVAx5wqAzVMHjY1hW6yFkHCHdkLdO-wTvz_2aPHz_9rC7q-9__fi5-3pf23bguR6oE9J0ppW0HUzTMjeCdq4H0Q2MGmgM64deOCv4YByTVIy8M8KaThhGu_aafDrFHmL4s0LKasZkwXu9QFiT6ksOlwMrYHMCbQwpRXDqEHHW8Vkxqo5m1V4dzaqj2eOumC1HH87pq5lhfD05qyzAxzOgk9XeRb1YTK-caCU7BX05cVBU_EWIKlmExcKIEWxWY8D__fECcaSZrw</recordid><startdate>20060201</startdate><enddate>20060201</enddate><creator>Kurata, Christine</creator><creator>Bradley, Kym</creator><creator>Gaus, Hans</creator><creator>Luu, Nhuy</creator><creator>Cedillo, Isaiah</creator><creator>Ravikumar, Vasulinga T.</creator><creator>Sooy, Kent Van</creator><creator>McArdle, James V.</creator><creator>Capaldi, Daniel C.</creator><general>Elsevier Ltd</general><general>Elsevier</general><scope>IQODW</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>7X8</scope></search><sort><creationdate>20060201</creationdate><title>Characterization of high molecular weight impurities in synthetic phosphorothioate oligonucleotides</title><author>Kurata, Christine ; Bradley, Kym ; Gaus, Hans ; Luu, Nhuy ; Cedillo, Isaiah ; Ravikumar, Vasulinga T. ; Sooy, Kent Van ; McArdle, James V. ; Capaldi, Daniel C.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c384t-80f79b5b39038b231fdeaff6e75810be2b16867fc748bf1907d45b7cb57b1053</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2006</creationdate><topic>5-Methylcytosine - chemistry</topic><topic>Analytical chemistry</topic><topic>Carbohydrates. Nucleosides and nucleotides</topic><topic>Chemistry</topic><topic>Chromatographic methods and physical methods associated with chromatography</topic><topic>Chromatography, High Pressure Liquid</topic><topic>Deoxyadenosines - chemistry</topic><topic>Exact sciences and technology</topic><topic>Liquid chromatography–mass spectrometry</topic><topic>Molecular Structure</topic><topic>Molecular Weight</topic><topic>Nucleosides, nucleotides and oligonucleotides</topic><topic>Oligonucleotides - chemical synthesis</topic><topic>Organic chemistry</topic><topic>Organophosphorus Compounds - chemistry</topic><topic>Other chromatographic methods</topic><topic>Phosphorothioate oligonucleotides</topic><topic>Preparations and properties</topic><topic>Spectrophotometry, Ultraviolet</topic><topic>Thionucleotides - chemistry</topic><topic>Universal solid support</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Kurata, Christine</creatorcontrib><creatorcontrib>Bradley, Kym</creatorcontrib><creatorcontrib>Gaus, Hans</creatorcontrib><creatorcontrib>Luu, Nhuy</creatorcontrib><creatorcontrib>Cedillo, Isaiah</creatorcontrib><creatorcontrib>Ravikumar, Vasulinga T.</creatorcontrib><creatorcontrib>Sooy, Kent Van</creatorcontrib><creatorcontrib>McArdle, James V.</creatorcontrib><creatorcontrib>Capaldi, Daniel C.</creatorcontrib><collection>Pascal-Francis</collection><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>Bioorganic & medicinal chemistry letters</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Kurata, Christine</au><au>Bradley, Kym</au><au>Gaus, Hans</au><au>Luu, Nhuy</au><au>Cedillo, Isaiah</au><au>Ravikumar, Vasulinga T.</au><au>Sooy, Kent Van</au><au>McArdle, James V.</au><au>Capaldi, Daniel C.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Characterization of high molecular weight impurities in synthetic phosphorothioate oligonucleotides</atitle><jtitle>Bioorganic & medicinal chemistry letters</jtitle><addtitle>Bioorg Med Chem Lett</addtitle><date>2006-02-01</date><risdate>2006</risdate><volume>16</volume><issue>3</issue><spage>607</spage><epage>614</epage><pages>607-614</pages><issn>0960-894X</issn><eissn>1464-3405</eissn><abstract>Phosphorothioate oligonucleotides manufactured by standard phosphoramidite techniques using nucleoside-loaded supports contain high molecular weight impurities of the type shown. These impurities are avoided if a novel universal solid support is used.
Phosphorothioate oligonucleotides manufactured by standard phosphoramidite techniques using 2′-deoxyadenosine- or 2′-
O-(2-methoxyethyl)-5-methylcytosine-loaded solid supports contain branched impurities consisting of two chains linked through the exocyclic amino group of the 3′-terminal nucleoside of one chain and the 3′-terminal hydroxyl group of another via a P(O)SH group. These impurities are not produced when a universal, non-nucleoside derivatized support is used.</abstract><cop>Oxford</cop><pub>Elsevier Ltd</pub><pmid>16274991</pmid><doi>10.1016/j.bmcl.2005.10.051</doi><tpages>8</tpages></addata></record> |
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| subjects | 5-Methylcytosine - chemistry Analytical chemistry Carbohydrates. Nucleosides and nucleotides Chemistry Chromatographic methods and physical methods associated with chromatography Chromatography, High Pressure Liquid Deoxyadenosines - chemistry Exact sciences and technology Liquid chromatography–mass spectrometry Molecular Structure Molecular Weight Nucleosides, nucleotides and oligonucleotides Oligonucleotides - chemical synthesis Organic chemistry Organophosphorus Compounds - chemistry Other chromatographic methods Phosphorothioate oligonucleotides Preparations and properties Spectrophotometry, Ultraviolet Thionucleotides - chemistry Universal solid support |
| title | Characterization of high molecular weight impurities in synthetic phosphorothioate oligonucleotides |
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