o-Nitrobenzenesulfonamides in Nucleoside Synthesis: Efficient 5‘-Aziridination of Adenosine
5‘-Aziridinoadenylates of the form 1 and a related nitrogen mustard variant have been constructed using a novel variation of the Mitsunobu reaction. Such molecules allow conversion of biological methyltransferases into nucleoside transferases, thus providing powerful tools for investigating S-adenos...
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| Veröffentlicht in: | Journal of organic chemistry 2005-07, Vol.70 (15), p.5833-5839 |
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| container_end_page | 5839 |
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| container_issue | 15 |
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| container_title | Journal of organic chemistry |
| container_volume | 70 |
| creator | Petersen, Scott G Rajski, Scott R |
| description | 5‘-Aziridinoadenylates of the form 1 and a related nitrogen mustard variant have been constructed using a novel variation of the Mitsunobu reaction. Such molecules allow conversion of biological methyltransferases into nucleoside transferases, thus providing powerful tools for investigating S-adenosyl-l-methionine (SAM)-dependent methylation. We present here a highly effective synthesis of such molecules that is amenable to aziridine diversification as well as elaboration of the base moiety so as to afford “bumped” cofactor mimics compatible with “hole”-bearing mutant proteins. |
| doi_str_mv | 10.1021/jo050205w |
| format | Article |
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Org. Chem</addtitle><description>5‘-Aziridinoadenylates of the form 1 and a related nitrogen mustard variant have been constructed using a novel variation of the Mitsunobu reaction. Such molecules allow conversion of biological methyltransferases into nucleoside transferases, thus providing powerful tools for investigating S-adenosyl-l-methionine (SAM)-dependent methylation. We present here a highly effective synthesis of such molecules that is amenable to aziridine diversification as well as elaboration of the base moiety so as to afford “bumped” cofactor mimics compatible with “hole”-bearing mutant proteins.</description><subject>Adenosine - analogs & derivatives</subject><subject>Adenosine - chemical synthesis</subject><subject>Aziridines - chemical synthesis</subject><subject>Carbohydrates. Nucleosides and nucleotides</subject><subject>Chemistry</subject><subject>DNA Nucleotidylexotransferase - metabolism</subject><subject>Exact sciences and technology</subject><subject>Heterocyclic compounds</subject><subject>Heterocyclic compounds with only one n hetero atom and condensed derivatives</subject><subject>Methylation</subject><subject>Methyltransferases - metabolism</subject><subject>Molecular Mimicry</subject><subject>Mustard Plant - metabolism</subject><subject>Nitrobenzenes - chemistry</subject><subject>Nucleosides - chemical synthesis</subject><subject>Nucleosides, nucleotides and oligonucleotides</subject><subject>Organic chemistry</subject><subject>Preparations and properties</subject><subject>S-Adenosylmethionine - chemistry</subject><subject>S-Adenosylmethionine - metabolism</subject><subject>Spectrum Analysis</subject><subject>Sulfonamides - chemistry</subject><issn>0022-3263</issn><issn>1520-6904</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2005</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNpt0M9qFTEUBvAgFnutLnwBmY2Ci2lPMpPMxN2l1GopVbgXXMYz-YOpc5OazKDtqlvfwOfrkxi5l9aF2YRwfvk4fIS8oHBIgdGjywgcGPAfj8iCcga1kNA-JgsAxuqGiWafPM35EsrhnD8h-1QA7UXHF-RLrC_8lOJgw40NNs-jiwE33thc-VBdzHq0MZdntboO01ebfX57d_urOnHOa2_DVPG729_18sYnb3zAycdQRVctjQ3lX7DPyJ7DMdvnu_uArN-drI_f1-cfTz8cL89rbHo61QMMVg8DB41StgzRiBawb7kDSWXXdkajQ67bljOp7WBMryWaBrHvKOjmgLzexl6l-H22eVIbn7UdRww2zlmJHhreUV7gmy3UKeacrFNXyW8wXSsK6m-b6r7NYl_uQudhY82D3NVXwKsdwKxxdAmD9vkfJ4VoKCuu3jqfJ_vzfo7pmxJd03G1_rRSctXLz_z0TK0fclHnss-cQqnuPwv-AbH7m0I</recordid><startdate>20050722</startdate><enddate>20050722</enddate><creator>Petersen, Scott G</creator><creator>Rajski, Scott R</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>20050722</creationdate><title>o-Nitrobenzenesulfonamides in Nucleoside Synthesis: Efficient 5‘-Aziridination of Adenosine</title><author>Petersen, Scott G ; Rajski, Scott R</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a381t-b0becbb50ca9942aad640a845f0919747dcafa5c44529cebdd8c9ad3aa8710c3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2005</creationdate><topic>Adenosine - analogs & derivatives</topic><topic>Adenosine - chemical synthesis</topic><topic>Aziridines - chemical synthesis</topic><topic>Carbohydrates. Nucleosides and nucleotides</topic><topic>Chemistry</topic><topic>DNA Nucleotidylexotransferase - metabolism</topic><topic>Exact sciences and technology</topic><topic>Heterocyclic compounds</topic><topic>Heterocyclic compounds with only one n hetero atom and condensed derivatives</topic><topic>Methylation</topic><topic>Methyltransferases - metabolism</topic><topic>Molecular Mimicry</topic><topic>Mustard Plant - metabolism</topic><topic>Nitrobenzenes - chemistry</topic><topic>Nucleosides - chemical synthesis</topic><topic>Nucleosides, nucleotides and oligonucleotides</topic><topic>Organic chemistry</topic><topic>Preparations and properties</topic><topic>S-Adenosylmethionine - chemistry</topic><topic>S-Adenosylmethionine - metabolism</topic><topic>Spectrum Analysis</topic><topic>Sulfonamides - chemistry</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Petersen, Scott G</creatorcontrib><creatorcontrib>Rajski, Scott R</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 organic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Petersen, Scott G</au><au>Rajski, Scott R</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>o-Nitrobenzenesulfonamides in Nucleoside Synthesis: Efficient 5‘-Aziridination of Adenosine</atitle><jtitle>Journal of organic chemistry</jtitle><addtitle>J. Org. Chem</addtitle><date>2005-07-22</date><risdate>2005</risdate><volume>70</volume><issue>15</issue><spage>5833</spage><epage>5839</epage><pages>5833-5839</pages><issn>0022-3263</issn><eissn>1520-6904</eissn><coden>JOCEAH</coden><abstract>5‘-Aziridinoadenylates of the form 1 and a related nitrogen mustard variant have been constructed using a novel variation of the Mitsunobu reaction. Such molecules allow conversion of biological methyltransferases into nucleoside transferases, thus providing powerful tools for investigating S-adenosyl-l-methionine (SAM)-dependent methylation. We present here a highly effective synthesis of such molecules that is amenable to aziridine diversification as well as elaboration of the base moiety so as to afford “bumped” cofactor mimics compatible with “hole”-bearing mutant proteins.</abstract><cop>Washington, DC</cop><pub>American Chemical Society</pub><pmid>16018675</pmid><doi>10.1021/jo050205w</doi><tpages>7</tpages></addata></record> |
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| ispartof | Journal of organic chemistry, 2005-07, Vol.70 (15), p.5833-5839 |
| issn | 0022-3263 1520-6904 |
| language | eng |
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| source | ACS Publications; MEDLINE |
| subjects | Adenosine - analogs & derivatives Adenosine - chemical synthesis Aziridines - chemical synthesis Carbohydrates. Nucleosides and nucleotides Chemistry DNA Nucleotidylexotransferase - metabolism Exact sciences and technology Heterocyclic compounds Heterocyclic compounds with only one n hetero atom and condensed derivatives Methylation Methyltransferases - metabolism Molecular Mimicry Mustard Plant - metabolism Nitrobenzenes - chemistry Nucleosides - chemical synthesis Nucleosides, nucleotides and oligonucleotides Organic chemistry Preparations and properties S-Adenosylmethionine - chemistry S-Adenosylmethionine - metabolism Spectrum Analysis Sulfonamides - chemistry |
| title | o-Nitrobenzenesulfonamides in Nucleoside Synthesis: Efficient 5‘-Aziridination of Adenosine |
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