Loading…

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′...

Full description

Saved in:
Bibliographic Details
Published in:Bioorganic & medicinal chemistry 2007-10, Vol.15 (20), p.6549-6555
Main Authors: Abramova, Tatiana V., Vasileva, Svetlana V., Serpokrylova, Inna Yu, Kless, Hadar, Silnikov, Vladimir N.
Format: Article
Language:English
Subjects:
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
cited_by cdi_FETCH-LOGICAL-c351t-3204cd421e9fb91943f0b86704eb30487aaa72b2b851c19ae8f37f62c4bf972e3
cites cdi_FETCH-LOGICAL-c351t-3204cd421e9fb91943f0b86704eb30487aaa72b2b851c19ae8f37f62c4bf972e3
container_end_page 6555
container_issue 20
container_start_page 6549
container_title Bioorganic & medicinal chemistry
container_volume 15
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
fullrecord <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_68205856</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><els_id>S0968089607006189</els_id><sourcerecordid>68205856</sourcerecordid><originalsourceid>FETCH-LOGICAL-c351t-3204cd421e9fb91943f0b86704eb30487aaa72b2b851c19ae8f37f62c4bf972e3</originalsourceid><addsrcrecordid>eNp9kMtKAzEUhoMotlYfwI3Myt3U3CaT4KoUb1Bwo-uQyZzQlLmZzBTc-Uw-kk_iDC24E344m-__4XwIXRO8JJiIu92yqO2SYpwvp2B6guaEC54ypsgpmmMlZIqlEjN0EeMOjwRX5BzNSC6kEIzM0XqVOGN9BYlpygScA9v7PSTxs-m3EH1MWpeUvhlsBW3vS0iyn6_vtA--27ax25oe4iU6c6aKcHW8C_T--PC2fk43r08v69UmtSwjfcoo5rbklIByhSKKM4cLKXLMoWCYy9wYk9OCFjIjligD0rHcCWp54VROgS3Q7WG3C-3HALHXtY8Wqso00A5RC0lxJjMxguQA2tDGGMDpLvjahE9NsJ7M6Z0ezenJnJ6C6di5OY4PRQ3lX-OoagTuDwCML-49BB2th8ZC6cMoTZet_2f-F_N8ftc</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>68205856</pqid></control><display><type>article</type><title>A facile and effective synthesis of dinucleotide 5′-triphosphates</title><source>Elsevier</source><creator>Abramova, Tatiana V. ; Vasileva, Svetlana V. ; Serpokrylova, Inna Yu ; Kless, Hadar ; Silnikov, Vladimir N.</creator><creatorcontrib>Abramova, Tatiana V. ; Vasileva, Svetlana V. ; Serpokrylova, Inna Yu ; Kless, Hadar ; Silnikov, Vladimir N.</creatorcontrib><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><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 &amp; 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 &amp; 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 &amp; 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 &amp; 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. 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.</abstract><cop>England</cop><pub>Elsevier Ltd</pub><pmid>17686631</pmid><doi>10.1016/j.bmc.2007.07.002</doi><tpages>7</tpages></addata></record>
fulltext fulltext
identifier ISSN: 0968-0896
ispartof Bioorganic & medicinal chemistry, 2007-10, Vol.15 (20), p.6549-6555
issn 0968-0896
1464-3391
language eng
recordid cdi_proquest_miscellaneous_68205856
source Elsevier
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
url http://sfxeu10.hosted.exlibrisgroup.com/loughborough?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2024-12-26T10%3A12%3A02IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-proquest_cross&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=A%20facile%20and%20effective%20synthesis%20of%20dinucleotide%205%E2%80%B2-triphosphates&rft.jtitle=Bioorganic%20&%20medicinal%20chemistry&rft.au=Abramova,%20Tatiana%20V.&rft.date=2007-10-15&rft.volume=15&rft.issue=20&rft.spage=6549&rft.epage=6555&rft.pages=6549-6555&rft.issn=0968-0896&rft.eissn=1464-3391&rft_id=info:doi/10.1016/j.bmc.2007.07.002&rft_dat=%3Cproquest_cross%3E68205856%3C/proquest_cross%3E%3Cgrp_id%3Ecdi_FETCH-LOGICAL-c351t-3204cd421e9fb91943f0b86704eb30487aaa72b2b851c19ae8f37f62c4bf972e3%3C/grp_id%3E%3Coa%3E%3C/oa%3E%3Curl%3E%3C/url%3E&rft_id=info:oai/&rft_pqid=68205856&rft_id=info:pmid/17686631&rfr_iscdi=true