Solid-Phase Synthesis of Multiantennary Oligonucleotide Glycoconjugates Utilizing On-Support Oximation
A novel method for preparation of multivalent oligonucleotide glycoconjugates on a solid support has been described. A pentaerythritol-based phosphoramidite (1) bearing two masked aminooxy groups has been used as the key building block. After conventional chain assembly, the aminooxy functions have...
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| Veröffentlicht in: | Bioconjugate chemistry 2004-07, Vol.15 (4), p.890-896 |
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| container_title | Bioconjugate chemistry |
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| creator | Katajisto, Johanna Virta, Pasi Lönnberg, Harri |
| description | A novel method for preparation of multivalent oligonucleotide glycoconjugates on a solid support has been described. A pentaerythritol-based phosphoramidite (1) bearing two masked aminooxy groups has been used as the key building block. After conventional chain assembly, the aminooxy functions have been deblocked by a hydrazinium acetate treatment and subsequently oximated with fully acetylated 4-oxobutyl α-d-mannopyranoside. The conjugates obtained have been shown to withstand standard ammonolytic deprotection and cleavage from the support. Four different oligonucleotide glycoconjugates containing two, four, or six α-d-mannopyranosyl units (12−15) have been prepared to demonstrate the applicability of the procedure. The glycosyl residues only moderately retards hybridization of the oligonucleotide moiety. |
| doi_str_mv | 10.1021/bc049955n |
| format | Article |
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The glycosyl residues only moderately retards hybridization of the oligonucleotide moiety.</description><identifier>ISSN: 1043-1802</identifier><identifier>EISSN: 1520-4812</identifier><identifier>DOI: 10.1021/bc049955n</identifier><identifier>PMID: 15264878</identifier><language>eng</language><publisher>United States: American Chemical Society</publisher><subject>Chemical synthesis ; Chemistry ; Chromatography, High Pressure Liquid ; Glycoconjugates - chemical synthesis ; Glycoconjugates - chemistry ; Ligands ; Mannose - chemistry ; Methods ; Molecular Structure ; Nucleic Acid Denaturation ; Oligonucleotides - chemical synthesis ; Oligonucleotides - chemistry ; Organophosphorus Compounds - chemical synthesis ; Organophosphorus Compounds - chemistry ; Solids ; Temperature</subject><ispartof>Bioconjugate chemistry, 2004-07, Vol.15 (4), p.890-896</ispartof><rights>Copyright © 2004 American Chemical Society</rights><rights>Copyright American Chemical Society Jul/Aug 2004</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a376t-c20e8e86a179b856fb7f58ffbdcadd25f82b37640a875a2951424b0325d103333</citedby><cites>FETCH-LOGICAL-a376t-c20e8e86a179b856fb7f58ffbdcadd25f82b37640a875a2951424b0325d103333</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/bc049955n$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/bc049955n$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,776,780,2752,27053,27901,27902,56713,56763</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/15264878$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Katajisto, Johanna</creatorcontrib><creatorcontrib>Virta, Pasi</creatorcontrib><creatorcontrib>Lönnberg, Harri</creatorcontrib><title>Solid-Phase Synthesis of Multiantennary Oligonucleotide Glycoconjugates Utilizing On-Support Oximation</title><title>Bioconjugate chemistry</title><addtitle>Bioconjugate Chem</addtitle><description>A novel method for preparation of multivalent oligonucleotide glycoconjugates on a solid support has been described. A pentaerythritol-based phosphoramidite (1) bearing two masked aminooxy groups has been used as the key building block. After conventional chain assembly, the aminooxy functions have been deblocked by a hydrazinium acetate treatment and subsequently oximated with fully acetylated 4-oxobutyl α-d-mannopyranoside. The conjugates obtained have been shown to withstand standard ammonolytic deprotection and cleavage from the support. Four different oligonucleotide glycoconjugates containing two, four, or six α-d-mannopyranosyl units (12−15) have been prepared to demonstrate the applicability of the procedure. The glycosyl residues only moderately retards hybridization of the oligonucleotide moiety.</description><subject>Chemical synthesis</subject><subject>Chemistry</subject><subject>Chromatography, High Pressure Liquid</subject><subject>Glycoconjugates - chemical synthesis</subject><subject>Glycoconjugates - chemistry</subject><subject>Ligands</subject><subject>Mannose - chemistry</subject><subject>Methods</subject><subject>Molecular Structure</subject><subject>Nucleic Acid Denaturation</subject><subject>Oligonucleotides - chemical synthesis</subject><subject>Oligonucleotides - chemistry</subject><subject>Organophosphorus Compounds - chemical synthesis</subject><subject>Organophosphorus Compounds - chemistry</subject><subject>Solids</subject><subject>Temperature</subject><issn>1043-1802</issn><issn>1520-4812</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2004</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNpl0FtrHCEYBmApKc2pF_0DZQi00Itp1BkPc1mWdtuyYVM2IbkTx9GNG1e36kA2v76GXRJIvVHw4Tu8AHxA8CuCGJ33CrZdR4h_A44QwbBuOcIH5Q3bpkYc4kNwnNIKQtghjt-Bw4Joyxk_AmYRnB3qyzuZdLXY-nynk01VMNXF6LKVPmvvZdxWc2eXwY_K6ZDtoKup26qggl-NS5l1qq6zdfbR-mU19_Vi3GxCzNX8wa5ltsGfgrdGuqTf7-8TcP3j-9XkZz2bT39Nvs1q2TCaa4Wh5ppTiVjXc0JNzwzhxvSDksOAieG4L7CFkjMicUdQi9seNpgMCDblnIDPu7qbGP6OOmWxtklp56TXYUyCUoYJw7TAs1dwFcboy2wCI4o4Q-wJfdkhFUNKURuxiWWhuBUIiqfkxXPyxX7cFxz7tR5e5D7qAuodsCnrh-d_Ge8FZQ0j4upyIaZ_ZjeTC34rfhf_aeelSi_D_d_4H7w0ml0</recordid><startdate>20040701</startdate><enddate>20040701</enddate><creator>Katajisto, Johanna</creator><creator>Virta, Pasi</creator><creator>Lönnberg, Harri</creator><general>American Chemical Society</general><scope>BSCLL</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>7QO</scope><scope>7TM</scope><scope>8FD</scope><scope>FR3</scope><scope>P64</scope><scope>7X8</scope></search><sort><creationdate>20040701</creationdate><title>Solid-Phase Synthesis of Multiantennary Oligonucleotide Glycoconjugates Utilizing On-Support Oximation</title><author>Katajisto, Johanna ; Virta, Pasi ; Lönnberg, Harri</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a376t-c20e8e86a179b856fb7f58ffbdcadd25f82b37640a875a2951424b0325d103333</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2004</creationdate><topic>Chemical synthesis</topic><topic>Chemistry</topic><topic>Chromatography, High Pressure Liquid</topic><topic>Glycoconjugates - chemical synthesis</topic><topic>Glycoconjugates - chemistry</topic><topic>Ligands</topic><topic>Mannose - chemistry</topic><topic>Methods</topic><topic>Molecular Structure</topic><topic>Nucleic Acid Denaturation</topic><topic>Oligonucleotides - chemical synthesis</topic><topic>Oligonucleotides - chemistry</topic><topic>Organophosphorus Compounds - chemical synthesis</topic><topic>Organophosphorus Compounds - chemistry</topic><topic>Solids</topic><topic>Temperature</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Katajisto, Johanna</creatorcontrib><creatorcontrib>Virta, Pasi</creatorcontrib><creatorcontrib>Lönnberg, Harri</creatorcontrib><collection>Istex</collection><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>Biotechnology Research Abstracts</collection><collection>Nucleic Acids Abstracts</collection><collection>Technology Research Database</collection><collection>Engineering Research Database</collection><collection>Biotechnology and BioEngineering Abstracts</collection><collection>MEDLINE - Academic</collection><jtitle>Bioconjugate chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Katajisto, Johanna</au><au>Virta, Pasi</au><au>Lönnberg, Harri</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Solid-Phase Synthesis of Multiantennary Oligonucleotide Glycoconjugates Utilizing On-Support Oximation</atitle><jtitle>Bioconjugate chemistry</jtitle><addtitle>Bioconjugate Chem</addtitle><date>2004-07-01</date><risdate>2004</risdate><volume>15</volume><issue>4</issue><spage>890</spage><epage>896</epage><pages>890-896</pages><issn>1043-1802</issn><eissn>1520-4812</eissn><abstract>A novel method for preparation of multivalent oligonucleotide glycoconjugates on a solid support has been described. 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| ispartof | Bioconjugate chemistry, 2004-07, Vol.15 (4), p.890-896 |
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| language | eng |
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| source | MEDLINE; American Chemical Society Journals |
| subjects | Chemical synthesis Chemistry Chromatography, High Pressure Liquid Glycoconjugates - chemical synthesis Glycoconjugates - chemistry Ligands Mannose - chemistry Methods Molecular Structure Nucleic Acid Denaturation Oligonucleotides - chemical synthesis Oligonucleotides - chemistry Organophosphorus Compounds - chemical synthesis Organophosphorus Compounds - chemistry Solids Temperature |
| title | Solid-Phase Synthesis of Multiantennary Oligonucleotide Glycoconjugates Utilizing On-Support Oximation |
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