Oxathiaphospholane Approach to the Synthesis of Oligodeoxyribonucleotides Containing Stereodefined Internucleotide Phosphoroselenoate Function
5‘-O-DMT-deoxyribonucleoside-3‘-O-(2-selena-4,4-pentamethylene-1,3,2-oxathiaphospholane) monomers, derivatives of dA, dC, dG, and T, can be resolved into pure P-diastereomers by silica gel column chromatography. They have been used for DBU-promoted, either solution- or solid-phase synthesis of P-ste...
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| Veröffentlicht in: | Organic letters 2005-09, Vol.7 (18), p.3901-3904 |
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| creator | Guga, Piotr Maciaszek, Anna Stec, Wojciech J |
| description | 5‘-O-DMT-deoxyribonucleoside-3‘-O-(2-selena-4,4-pentamethylene-1,3,2-oxathiaphospholane) monomers, derivatives of dA, dC, dG, and T, can be resolved into pure P-diastereomers by silica gel column chromatography. They have been used for DBU-promoted, either solution- or solid-phase synthesis of P-stereodefined phosphoroselenoate analogues of oligodeoxyribonucleotides. Fast- and slow-eluting monomers are precursors of phosphoroselenoate internucleotide linkage of R P and S P absolute configuration, respectively. |
| doi_str_mv | 10.1021/ol051302e |
| format | Article |
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They have been used for DBU-promoted, either solution- or solid-phase synthesis of P-stereodefined phosphoroselenoate analogues of oligodeoxyribonucleotides. Fast- and slow-eluting monomers are precursors of phosphoroselenoate internucleotide linkage of R P and S P absolute configuration, respectively.</description><identifier>ISSN: 1523-7060</identifier><identifier>EISSN: 1523-7052</identifier><identifier>DOI: 10.1021/ol051302e</identifier><identifier>PMID: 16119927</identifier><language>eng</language><publisher>United States: American Chemical Society</publisher><subject>Molecular Structure ; Nucleotides - chemistry ; Oligodeoxyribonucleotides - chemical synthesis ; Oligodeoxyribonucleotides - chemistry ; Organoselenium Compounds - chemical synthesis ; Organoselenium Compounds - chemistry ; Ribose - analogs & derivatives ; Ribose - chemistry ; Stereoisomerism</subject><ispartof>Organic letters, 2005-09, Vol.7 (18), p.3901-3904</ispartof><rights>Copyright © 2005 American Chemical Society</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a379t-51067c6fbbbf00b656377b58cc5b6b2234b85e94afdda8316311109dbeaabd383</citedby><cites>FETCH-LOGICAL-a379t-51067c6fbbbf00b656377b58cc5b6b2234b85e94afdda8316311109dbeaabd383</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/ol051302e$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/ol051302e$$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/16119927$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Guga, Piotr</creatorcontrib><creatorcontrib>Maciaszek, Anna</creatorcontrib><creatorcontrib>Stec, Wojciech J</creatorcontrib><title>Oxathiaphospholane Approach to the Synthesis of Oligodeoxyribonucleotides Containing Stereodefined Internucleotide Phosphoroselenoate Function</title><title>Organic letters</title><addtitle>Org. 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Fast- and slow-eluting monomers are precursors of phosphoroselenoate internucleotide linkage of R P and S P absolute configuration, respectively.</description><subject>Molecular Structure</subject><subject>Nucleotides - chemistry</subject><subject>Oligodeoxyribonucleotides - chemical synthesis</subject><subject>Oligodeoxyribonucleotides - chemistry</subject><subject>Organoselenium Compounds - chemical synthesis</subject><subject>Organoselenium Compounds - chemistry</subject><subject>Ribose - analogs & derivatives</subject><subject>Ribose - chemistry</subject><subject>Stereoisomerism</subject><issn>1523-7060</issn><issn>1523-7052</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2005</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNptkMFOAjEQhhujEUQPvoDpRRMPaLul3d0jIaIkJJig503bnYWSpcVtN4GX8JktgcDFQzPt5Jt_-v8I3VPyQklCX11NOGUkgQvUpTxh_ZTw5PJ0F6SDbrxfEUJjJ79GHSoozfMk7aLf2VaGpZGbpfPx1NICHm42jZN6iYPDYQl4vrOxeOOxq_CsNgtXgtvuGqOcbXUNLpgSPB45G6Sxxi7wPEADkaqMhRJPbHyeSfx52NU4DzVYJwPgcWt1MM7eoqtK1h7ujrWHvsdvX6OP_nT2PhkNp33J0jz0OSUi1aJSSlWEKMEFS1PFM625EipJ2EBlHPKBrMpSZowKRiklealASlWyjPXQ00E3Ov1pwYdibbyGeu_ftb4QGY9DgySCzwdQx-_6Bqpi05i1bHYFJcU-_OIUfmQfjqKtWkN5Jo9pR-DxAEjti5VrGxs9_iP0Bx0OkGk</recordid><startdate>20050901</startdate><enddate>20050901</enddate><creator>Guga, Piotr</creator><creator>Maciaszek, Anna</creator><creator>Stec, Wojciech J</creator><general>American Chemical Society</general><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>20050901</creationdate><title>Oxathiaphospholane Approach to the Synthesis of Oligodeoxyribonucleotides Containing Stereodefined Internucleotide Phosphoroselenoate Function</title><author>Guga, Piotr ; Maciaszek, Anna ; Stec, Wojciech J</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a379t-51067c6fbbbf00b656377b58cc5b6b2234b85e94afdda8316311109dbeaabd383</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2005</creationdate><topic>Molecular Structure</topic><topic>Nucleotides - chemistry</topic><topic>Oligodeoxyribonucleotides - chemical synthesis</topic><topic>Oligodeoxyribonucleotides - chemistry</topic><topic>Organoselenium Compounds - chemical synthesis</topic><topic>Organoselenium Compounds - chemistry</topic><topic>Ribose - analogs & derivatives</topic><topic>Ribose - chemistry</topic><topic>Stereoisomerism</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Guga, Piotr</creatorcontrib><creatorcontrib>Maciaszek, Anna</creatorcontrib><creatorcontrib>Stec, Wojciech J</creatorcontrib><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>Organic letters</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Guga, Piotr</au><au>Maciaszek, Anna</au><au>Stec, Wojciech J</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Oxathiaphospholane Approach to the Synthesis of Oligodeoxyribonucleotides Containing Stereodefined Internucleotide Phosphoroselenoate Function</atitle><jtitle>Organic letters</jtitle><addtitle>Org. 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| identifier | ISSN: 1523-7060 |
| ispartof | Organic letters, 2005-09, Vol.7 (18), p.3901-3904 |
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| source | MEDLINE; American Chemical Society Journals |
| subjects | Molecular Structure Nucleotides - chemistry Oligodeoxyribonucleotides - chemical synthesis Oligodeoxyribonucleotides - chemistry Organoselenium Compounds - chemical synthesis Organoselenium Compounds - chemistry Ribose - analogs & derivatives Ribose - chemistry Stereoisomerism |
| title | Oxathiaphospholane Approach to the Synthesis of Oligodeoxyribonucleotides Containing Stereodefined Internucleotide Phosphoroselenoate Function |
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