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A facile and effective synthesis of dinucleotide 5′-triphosphates
Successful synthetic procedure for the conversion of 5′-monophosphorylated 2′-deoxydinucleotides into their 5′-triphosphate derivatives in satisfactory to excellent yields. We report on the successful synthetic procedure for the conversion of 5′-monophosphorylated 2′-deoxydinucleotides into their 5′...
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Published in: | Bioorganic & medicinal chemistry 2007-10, Vol.15 (20), p.6549-6555 |
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creator | Abramova, Tatiana V. Vasileva, Svetlana V. Serpokrylova, Inna Yu Kless, Hadar Silnikov, Vladimir N. |
description | Successful synthetic procedure for the conversion of 5′-monophosphorylated 2′-deoxydinucleotides into their 5′-triphosphate derivatives in satisfactory to excellent yields.
We report on the successful synthetic procedure for the conversion of 5′-monophosphorylated 2′-deoxydinucleotides into their 5′-triphosphate derivatives in satisfactory to excellent yields. The activation of the terminal phosphate group was achieved under the Mukaiyama conditions in the presence of a nucleophilic catalyst. The reaction conditions (solvent, counter ions, activation time and reagent excess) were optimized for all dinucleotides. |
doi_str_mv | 10.1016/j.bmc.2007.07.002 |
format | article |
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We report on the successful synthetic procedure for the conversion of 5′-monophosphorylated 2′-deoxydinucleotides into their 5′-triphosphate derivatives in satisfactory to excellent yields. The activation of the terminal phosphate group was achieved under the Mukaiyama conditions in the presence of a nucleophilic catalyst. The reaction conditions (solvent, counter ions, activation time and reagent excess) were optimized for all dinucleotides.</description><identifier>ISSN: 0968-0896</identifier><identifier>EISSN: 1464-3391</identifier><identifier>DOI: 10.1016/j.bmc.2007.07.002</identifier><identifier>PMID: 17686631</identifier><language>eng</language><publisher>England: Elsevier Ltd</publisher><subject>Chromatography, Ion Exchange ; Dinucleoside Phosphates - chemical synthesis ; Dinucleoside Phosphates - chemistry ; Furans - chemistry ; Kinetics ; Magnetic Resonance Spectroscopy ; Molecular Structure ; Oligonucleotides ; Stereoisomerism ; Terminal phosphate activation ; Triphosphates</subject><ispartof>Bioorganic & medicinal chemistry, 2007-10, Vol.15 (20), p.6549-6555</ispartof><rights>2007 Elsevier Ltd</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c351t-3204cd421e9fb91943f0b86704eb30487aaa72b2b851c19ae8f37f62c4bf972e3</citedby><cites>FETCH-LOGICAL-c351t-3204cd421e9fb91943f0b86704eb30487aaa72b2b851c19ae8f37f62c4bf972e3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,27924,27925</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/17686631$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Abramova, Tatiana V.</creatorcontrib><creatorcontrib>Vasileva, Svetlana V.</creatorcontrib><creatorcontrib>Serpokrylova, Inna Yu</creatorcontrib><creatorcontrib>Kless, Hadar</creatorcontrib><creatorcontrib>Silnikov, Vladimir N.</creatorcontrib><title>A facile and effective synthesis of dinucleotide 5′-triphosphates</title><title>Bioorganic & medicinal chemistry</title><addtitle>Bioorg Med Chem</addtitle><description>Successful synthetic procedure for the conversion of 5′-monophosphorylated 2′-deoxydinucleotides into their 5′-triphosphate derivatives in satisfactory to excellent yields.
We report on the successful synthetic procedure for the conversion of 5′-monophosphorylated 2′-deoxydinucleotides into their 5′-triphosphate derivatives in satisfactory to excellent yields. The activation of the terminal phosphate group was achieved under the Mukaiyama conditions in the presence of a nucleophilic catalyst. The reaction conditions (solvent, counter ions, activation time and reagent excess) were optimized for all dinucleotides.</description><subject>Chromatography, Ion Exchange</subject><subject>Dinucleoside Phosphates - chemical synthesis</subject><subject>Dinucleoside Phosphates - chemistry</subject><subject>Furans - chemistry</subject><subject>Kinetics</subject><subject>Magnetic Resonance Spectroscopy</subject><subject>Molecular Structure</subject><subject>Oligonucleotides</subject><subject>Stereoisomerism</subject><subject>Terminal phosphate activation</subject><subject>Triphosphates</subject><issn>0968-0896</issn><issn>1464-3391</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2007</creationdate><recordtype>article</recordtype><recordid>eNp9kMtKAzEUhoMotlYfwI3Myt3U3CaT4KoUb1Bwo-uQyZzQlLmZzBTc-Uw-kk_iDC24E344m-__4XwIXRO8JJiIu92yqO2SYpwvp2B6guaEC54ypsgpmmMlZIqlEjN0EeMOjwRX5BzNSC6kEIzM0XqVOGN9BYlpygScA9v7PSTxs-m3EH1MWpeUvhlsBW3vS0iyn6_vtA--27ax25oe4iU6c6aKcHW8C_T--PC2fk43r08v69UmtSwjfcoo5rbklIByhSKKM4cLKXLMoWCYy9wYk9OCFjIjligD0rHcCWp54VROgS3Q7WG3C-3HALHXtY8Wqso00A5RC0lxJjMxguQA2tDGGMDpLvjahE9NsJ7M6Z0ezenJnJ6C6di5OY4PRQ3lX-OoagTuDwCML-49BB2th8ZC6cMoTZet_2f-F_N8ftc</recordid><startdate>20071015</startdate><enddate>20071015</enddate><creator>Abramova, Tatiana V.</creator><creator>Vasileva, Svetlana V.</creator><creator>Serpokrylova, Inna Yu</creator><creator>Kless, Hadar</creator><creator>Silnikov, Vladimir N.</creator><general>Elsevier Ltd</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>20071015</creationdate><title>A facile and effective synthesis of dinucleotide 5′-triphosphates</title><author>Abramova, Tatiana V. ; Vasileva, Svetlana V. ; Serpokrylova, Inna Yu ; Kless, Hadar ; Silnikov, Vladimir N.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c351t-3204cd421e9fb91943f0b86704eb30487aaa72b2b851c19ae8f37f62c4bf972e3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2007</creationdate><topic>Chromatography, Ion Exchange</topic><topic>Dinucleoside Phosphates - chemical synthesis</topic><topic>Dinucleoside Phosphates - chemistry</topic><topic>Furans - chemistry</topic><topic>Kinetics</topic><topic>Magnetic Resonance Spectroscopy</topic><topic>Molecular Structure</topic><topic>Oligonucleotides</topic><topic>Stereoisomerism</topic><topic>Terminal phosphate activation</topic><topic>Triphosphates</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Abramova, Tatiana V.</creatorcontrib><creatorcontrib>Vasileva, Svetlana V.</creatorcontrib><creatorcontrib>Serpokrylova, Inna Yu</creatorcontrib><creatorcontrib>Kless, Hadar</creatorcontrib><creatorcontrib>Silnikov, Vladimir N.</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>Bioorganic & medicinal chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Abramova, Tatiana V.</au><au>Vasileva, Svetlana V.</au><au>Serpokrylova, Inna Yu</au><au>Kless, Hadar</au><au>Silnikov, Vladimir N.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>A facile and effective synthesis of dinucleotide 5′-triphosphates</atitle><jtitle>Bioorganic & medicinal chemistry</jtitle><addtitle>Bioorg Med Chem</addtitle><date>2007-10-15</date><risdate>2007</risdate><volume>15</volume><issue>20</issue><spage>6549</spage><epage>6555</epage><pages>6549-6555</pages><issn>0968-0896</issn><eissn>1464-3391</eissn><abstract>Successful synthetic procedure for the conversion of 5′-monophosphorylated 2′-deoxydinucleotides into their 5′-triphosphate derivatives in satisfactory to excellent yields.
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subjects | Chromatography, Ion Exchange Dinucleoside Phosphates - chemical synthesis Dinucleoside Phosphates - chemistry Furans - chemistry Kinetics Magnetic Resonance Spectroscopy Molecular Structure Oligonucleotides Stereoisomerism Terminal phosphate activation Triphosphates |
title | A facile and effective synthesis of dinucleotide 5′-triphosphates |
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