Synthesis of α-P-Modified Nucleoside Diphosphates with Ethylenediamine
This report describes a one-pot synthesis of α-P-borano-, α-P-thio-, and α-P-seleno-modified nucleoside diphosphate analogues that are otherwise difficult to obtain. The key step involves the intramolecular nucleophilic attack by an amino group in 5 to remove the γ-phosphate. The absolute configurat...
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| Veröffentlicht in: | Journal of the American Chemical Society 2005-12, Vol.127 (48), p.16782-16783 |
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| container_end_page | 16783 |
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| container_issue | 48 |
| container_start_page | 16782 |
| container_title | Journal of the American Chemical Society |
| container_volume | 127 |
| creator | Li, Ping Xu, Zhihong Liu, Hongyan Wennefors, Charlotta K Dobrikov, Mikhail I Ludwig, János Shaw, Barbara Ramsay |
| description | This report describes a one-pot synthesis of α-P-borano-, α-P-thio-, and α-P-seleno-modified nucleoside diphosphate analogues that are otherwise difficult to obtain. The key step involves the intramolecular nucleophilic attack by an amino group in 5 to remove the γ-phosphate. The absolute configurations of P-diastereomers were confirmed by analysis of their 1H NMR. Affinity studies revealed that the nucleoside boranodiphosphates are potentially useful in antiviral research. |
| doi_str_mv | 10.1021/ja055179y |
| format | Article |
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The key step involves the intramolecular nucleophilic attack by an amino group in 5 to remove the γ-phosphate. The absolute configurations of P-diastereomers were confirmed by analysis of their 1H NMR. Affinity studies revealed that the nucleoside boranodiphosphates are potentially useful in antiviral research.</description><identifier>ISSN: 0002-7863</identifier><identifier>EISSN: 1520-5126</identifier><identifier>DOI: 10.1021/ja055179y</identifier><identifier>PMID: 16316213</identifier><identifier>CODEN: JACSAT</identifier><language>eng</language><publisher>Washington, DC: American Chemical Society</publisher><subject>Adenosine Diphosphate - analogs & derivatives ; Animals ; Carbohydrates. 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Am. Chem. Soc</addtitle><description>This report describes a one-pot synthesis of α-P-borano-, α-P-thio-, and α-P-seleno-modified nucleoside diphosphate analogues that are otherwise difficult to obtain. The key step involves the intramolecular nucleophilic attack by an amino group in 5 to remove the γ-phosphate. The absolute configurations of P-diastereomers were confirmed by analysis of their 1H NMR. Affinity studies revealed that the nucleoside boranodiphosphates are potentially useful in antiviral research.</description><subject>Adenosine Diphosphate - analogs & derivatives</subject><subject>Animals</subject><subject>Carbohydrates. Nucleosides and nucleotides</subject><subject>Chemistry</subject><subject>Creatine Kinase - metabolism</subject><subject>Ethylenediamines - chemistry</subject><subject>Exact sciences and technology</subject><subject>Molecular Conformation</subject><subject>Muscles - enzymology</subject><subject>Muscles - metabolism</subject><subject>Nucleosides, nucleotides and oligonucleotides</subject><subject>Nucleotides - chemical synthesis</subject><subject>Nucleotides - metabolism</subject><subject>Organic chemistry</subject><subject>Preparations and properties</subject><subject>Pyruvate Kinase - metabolism</subject><subject>Rabbits</subject><issn>0002-7863</issn><issn>1520-5126</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2005</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNpt0M9u00AQBvAVoqKhcOAFkC8gcXDZ2f85olJapLRUahGIy2qzO5Y3OHbqsQV5LF6EZ8JVoubCaTXanz7NfIy9An4KXMD7VeBag51vn7AZaMFLDcI8ZTPOuSitM_KYPSdaTaMSDp6xYzASjAA5Yxe323aokTIVXVX8_VPelFddylXGVFyPscGOcsLiY97UHW3qMCAVv_JQF-dDvW2wxZTDOrf4gh1VoSF8uX9P2NdP53dnl-Xiy8Xnsw-LMkgHQ-mU4M4BmhTTEnmlbExzqe1STculOQcVUApwQocQraymY4ziClKMRjm5lCfs7S5303f3I9Lg15kiNk1osRvJG-eUcVpO8N0Oxr4j6rHymz6vQ7_1wP1Da_6xtcm-3oeOyzWmg9zXNIE3exAohqbqQxszHZyV4Li0kyt3LtOAvx__Q__TGyut9nc3t_6Sf4MfVwvtvx9yQyS_6sa-nbr7z4L_ADbHjzQ</recordid><startdate>20051207</startdate><enddate>20051207</enddate><creator>Li, Ping</creator><creator>Xu, Zhihong</creator><creator>Liu, Hongyan</creator><creator>Wennefors, Charlotta K</creator><creator>Dobrikov, Mikhail I</creator><creator>Ludwig, János</creator><creator>Shaw, Barbara Ramsay</creator><general>American Chemical Society</general><scope>BSCLL</scope><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>20051207</creationdate><title>Synthesis of α-P-Modified Nucleoside Diphosphates with Ethylenediamine</title><author>Li, Ping ; Xu, Zhihong ; Liu, Hongyan ; Wennefors, Charlotta K ; Dobrikov, Mikhail I ; Ludwig, János ; Shaw, Barbara Ramsay</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a381t-8420881e6dcdbe0f47cd9357b4000d9014ae321825aac73f52064041dcc6483b3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2005</creationdate><topic>Adenosine Diphosphate - analogs & derivatives</topic><topic>Animals</topic><topic>Carbohydrates. Nucleosides and nucleotides</topic><topic>Chemistry</topic><topic>Creatine Kinase - metabolism</topic><topic>Ethylenediamines - chemistry</topic><topic>Exact sciences and technology</topic><topic>Molecular Conformation</topic><topic>Muscles - enzymology</topic><topic>Muscles - metabolism</topic><topic>Nucleosides, nucleotides and oligonucleotides</topic><topic>Nucleotides - chemical synthesis</topic><topic>Nucleotides - metabolism</topic><topic>Organic chemistry</topic><topic>Preparations and properties</topic><topic>Pyruvate Kinase - metabolism</topic><topic>Rabbits</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Li, Ping</creatorcontrib><creatorcontrib>Xu, Zhihong</creatorcontrib><creatorcontrib>Liu, Hongyan</creatorcontrib><creatorcontrib>Wennefors, Charlotta K</creatorcontrib><creatorcontrib>Dobrikov, Mikhail I</creatorcontrib><creatorcontrib>Ludwig, János</creatorcontrib><creatorcontrib>Shaw, Barbara Ramsay</creatorcontrib><collection>Istex</collection><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>Journal of the American Chemical Society</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Li, Ping</au><au>Xu, Zhihong</au><au>Liu, Hongyan</au><au>Wennefors, Charlotta K</au><au>Dobrikov, Mikhail I</au><au>Ludwig, János</au><au>Shaw, Barbara Ramsay</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis of α-P-Modified Nucleoside Diphosphates with Ethylenediamine</atitle><jtitle>Journal of the American Chemical Society</jtitle><addtitle>J. Am. Chem. Soc</addtitle><date>2005-12-07</date><risdate>2005</risdate><volume>127</volume><issue>48</issue><spage>16782</spage><epage>16783</epage><pages>16782-16783</pages><issn>0002-7863</issn><eissn>1520-5126</eissn><coden>JACSAT</coden><abstract>This report describes a one-pot synthesis of α-P-borano-, α-P-thio-, and α-P-seleno-modified nucleoside diphosphate analogues that are otherwise difficult to obtain. The key step involves the intramolecular nucleophilic attack by an amino group in 5 to remove the γ-phosphate. The absolute configurations of P-diastereomers were confirmed by analysis of their 1H NMR. Affinity studies revealed that the nucleoside boranodiphosphates are potentially useful in antiviral research.</abstract><cop>Washington, DC</cop><pub>American Chemical Society</pub><pmid>16316213</pmid><doi>10.1021/ja055179y</doi><tpages>2</tpages></addata></record> |
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| subjects | Adenosine Diphosphate - analogs & derivatives Animals Carbohydrates. Nucleosides and nucleotides Chemistry Creatine Kinase - metabolism Ethylenediamines - chemistry Exact sciences and technology Molecular Conformation Muscles - enzymology Muscles - metabolism Nucleosides, nucleotides and oligonucleotides Nucleotides - chemical synthesis Nucleotides - metabolism Organic chemistry Preparations and properties Pyruvate Kinase - metabolism Rabbits |
| title | Synthesis of α-P-Modified Nucleoside Diphosphates with Ethylenediamine |
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