Chemical synthesis of 2'-deoxyoligonucleotides containing 5-fluoro-2'-deoxycytidine
2'-Deoxyoligonucleotides with 5-fluorocytosine residues incorporated at specific positions of the nucleotide sequence are tools of great potential in the study of the catalytic mechanism by which DNA cytosine methyltransferases methylate the 5-position of DNA cytosine residues in specific seque...
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| Veröffentlicht in: | Nucleic acids research 1992-05, Vol.20 (10), p.2421-2426 |
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| creator | SCHMIDT, S PEIN, C.-D FRITZ, H.-J CECH, D |
| description | 2'-Deoxyoligonucleotides with 5-fluorocytosine residues incorporated at specific positions of the nucleotide sequence are tools of great potential in the study of the catalytic mechanism by which DNA cytosine methyltransferases methylate the 5-position of DNA cytosine residues in specific sequence contexts. Chemical synthesis of such oligonucleotides is described. Two alternative approaches have been developed, one of which proceeds via a fully protected phosphoramidite of 5-fluoro-4-methylmercapto-2'-deoxyuridine 2, the other via a fully protected phosphoramidite of 5-fluoro-2'-deoxycytidine 3. Either building block can be used in automated oligonucleotide synthesis applying standard elongation cycles and deprotection procedures exclusively. The methylmercapto function of 2 is replaced by an amino group in the final ammonia treatment used for cleavage from support and base deprotection. |
| doi_str_mv | 10.1093/nar/20.10.2421 |
| format | Article |
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Chemical synthesis of such oligonucleotides is described. Two alternative approaches have been developed, one of which proceeds via a fully protected phosphoramidite of 5-fluoro-4-methylmercapto-2'-deoxyuridine 2, the other via a fully protected phosphoramidite of 5-fluoro-2'-deoxycytidine 3. Either building block can be used in automated oligonucleotide synthesis applying standard elongation cycles and deprotection procedures exclusively. The methylmercapto function of 2 is replaced by an amino group in the final ammonia treatment used for cleavage from support and base deprotection.</description><identifier>ISSN: 0305-1048</identifier><identifier>EISSN: 1362-4962</identifier><identifier>DOI: 10.1093/nar/20.10.2421</identifier><identifier>PMID: 1598200</identifier><identifier>CODEN: NARHAD</identifier><language>eng</language><publisher>Oxford: Oxford University Press</publisher><subject>Base Sequence ; Biological and medical sciences ; Biotechnology ; Chromatography, High Pressure Liquid ; Deoxycytidine - analogs & derivatives ; Deoxycytidine - analysis ; Deoxycytidine - chemistry ; Fundamental and applied biological sciences. Psychology ; Genetic engineering ; Genetic technics ; Methods. Procedures. Technologies ; Molecular Sequence Data ; Oligodeoxyribonucleotides - chemical synthesis ; Oligodeoxyribonucleotides - chemistry ; Synthetic digonucleotides and genes. 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Chemical synthesis of such oligonucleotides is described. Two alternative approaches have been developed, one of which proceeds via a fully protected phosphoramidite of 5-fluoro-4-methylmercapto-2'-deoxyuridine 2, the other via a fully protected phosphoramidite of 5-fluoro-2'-deoxycytidine 3. Either building block can be used in automated oligonucleotide synthesis applying standard elongation cycles and deprotection procedures exclusively. The methylmercapto function of 2 is replaced by an amino group in the final ammonia treatment used for cleavage from support and base deprotection.</description><subject>Base Sequence</subject><subject>Biological and medical sciences</subject><subject>Biotechnology</subject><subject>Chromatography, High Pressure Liquid</subject><subject>Deoxycytidine - analogs & derivatives</subject><subject>Deoxycytidine - analysis</subject><subject>Deoxycytidine - chemistry</subject><subject>Fundamental and applied biological sciences. Psychology</subject><subject>Genetic engineering</subject><subject>Genetic technics</subject><subject>Methods. Procedures. Technologies</subject><subject>Molecular Sequence Data</subject><subject>Oligodeoxyribonucleotides - chemical synthesis</subject><subject>Oligodeoxyribonucleotides - chemistry</subject><subject>Synthetic digonucleotides and genes. 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Psychology</topic><topic>Genetic engineering</topic><topic>Genetic technics</topic><topic>Methods. Procedures. Technologies</topic><topic>Molecular Sequence Data</topic><topic>Oligodeoxyribonucleotides - chemical synthesis</topic><topic>Oligodeoxyribonucleotides - chemistry</topic><topic>Synthetic digonucleotides and genes. Sequencing</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>SCHMIDT, S</creatorcontrib><creatorcontrib>PEIN, C.-D</creatorcontrib><creatorcontrib>FRITZ, H.-J</creatorcontrib><creatorcontrib>CECH, D</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>Nucleic Acids Abstracts</collection><collection>MEDLINE - Academic</collection><collection>PubMed Central (Full Participant titles)</collection><jtitle>Nucleic acids research</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>SCHMIDT, S</au><au>PEIN, C.-D</au><au>FRITZ, H.-J</au><au>CECH, D</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Chemical synthesis of 2'-deoxyoligonucleotides containing 5-fluoro-2'-deoxycytidine</atitle><jtitle>Nucleic acids research</jtitle><addtitle>Nucleic Acids Res</addtitle><date>1992-05-25</date><risdate>1992</risdate><volume>20</volume><issue>10</issue><spage>2421</spage><epage>2426</epage><pages>2421-2426</pages><issn>0305-1048</issn><eissn>1362-4962</eissn><coden>NARHAD</coden><abstract>2'-Deoxyoligonucleotides with 5-fluorocytosine residues incorporated at specific positions of the nucleotide sequence are tools of great potential in the study of the catalytic mechanism by which DNA cytosine methyltransferases methylate the 5-position of DNA cytosine residues in specific sequence contexts. Chemical synthesis of such oligonucleotides is described. Two alternative approaches have been developed, one of which proceeds via a fully protected phosphoramidite of 5-fluoro-4-methylmercapto-2'-deoxyuridine 2, the other via a fully protected phosphoramidite of 5-fluoro-2'-deoxycytidine 3. Either building block can be used in automated oligonucleotide synthesis applying standard elongation cycles and deprotection procedures exclusively. The methylmercapto function of 2 is replaced by an amino group in the final ammonia treatment used for cleavage from support and base deprotection.</abstract><cop>Oxford</cop><pub>Oxford University Press</pub><pmid>1598200</pmid><doi>10.1093/nar/20.10.2421</doi><tpages>6</tpages><oa>free_for_read</oa></addata></record> |
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| identifier | ISSN: 0305-1048 |
| ispartof | Nucleic acids research, 1992-05, Vol.20 (10), p.2421-2426 |
| issn | 0305-1048 1362-4962 |
| language | eng |
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| source | Oxford University Press Journals Digital Archive legacy; MEDLINE; PubMed Central |
| subjects | Base Sequence Biological and medical sciences Biotechnology Chromatography, High Pressure Liquid Deoxycytidine - analogs & derivatives Deoxycytidine - analysis Deoxycytidine - chemistry Fundamental and applied biological sciences. Psychology Genetic engineering Genetic technics Methods. Procedures. Technologies Molecular Sequence Data Oligodeoxyribonucleotides - chemical synthesis Oligodeoxyribonucleotides - chemistry Synthetic digonucleotides and genes. Sequencing |
| title | Chemical synthesis of 2'-deoxyoligonucleotides containing 5-fluoro-2'-deoxycytidine |
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