An improved process for the release of synthetic DNA sequences from a solid-phase capture support

Here, to facilitate the solid-phase purification of synthetic DNA sequences, a riboside phosphoramidite, carrying a 5-O-capture linker and a 2-O-silyl ether protecting group, is incorporated into a DNA sequence during its last solid-phase synthesis cycle. After deprotection and release of the DNA se...

Ausführliche Beschreibung

Gespeichert in:
Bibliographische Detailangaben
Veröffentlicht in:Tetrahedron letters 2022-08, Vol.106
Hauptverfasser: Grajkowski, Andrzej, Cawrse, Brian M., Takahashi, Mayumi, Beaucage, Serge L.
Format: Artikel
Sprache:eng
Schlagworte:
Online-Zugang:Volltext
Tags: Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
container_end_page
container_issue
container_start_page
container_title Tetrahedron letters
container_volume 106
creator Grajkowski, Andrzej
Cawrse, Brian M.
Takahashi, Mayumi
Beaucage, Serge L.
description Here, to facilitate the solid-phase purification of synthetic DNA sequences, a riboside phosphoramidite, carrying a 5-O-capture linker and a 2-O-silyl ether protecting group, is incorporated into a DNA sequence during its last solid-phase synthesis cycle. After deprotection and release of the DNA sequence from the synthesis support, the sequence is then covalently linked to a capture support to enable the removal of shorter unbound DNA sequences by simply washing these off the support. The solid-phase purified DNA sequence is then released from the capture support, through an innovative intramolecular cyclodeesterification of its terminal riboside ethyl phosphate triester entity and is isolated in a yield of 94% while displaying an exquisite purity of 97%.
format Article
fullrecord <record><control><sourceid>osti</sourceid><recordid>TN_cdi_osti_scitechconnect_1981776</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>1981776</sourcerecordid><originalsourceid>FETCH-osti_scitechconnect_19817763</originalsourceid><addsrcrecordid>eNqNyksKwjAUheEgCtbHHi7OCymtbTosPnDkyLmE9JZG2iTmpoK7N4IL8Ex-OHwzlmSiytN8L7I5SzgveFrwvF6yFdGDx5WCJ0w2BvTovH1hCzEKiaCzHkKP4HFASQi2A3qb-ASt4HhtgPA5oYkWOm9HkEB20G3q-q9W0oXJI9DknPVhwxadHAi3v67Z7ny6HS6ppaDvpHRA1StrDKpwz2qRVVWZ_4U-usNGiQ</addsrcrecordid><sourcetype>Open Access Repository</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype></control><display><type>article</type><title>An improved process for the release of synthetic DNA sequences from a solid-phase capture support</title><source>Elsevier ScienceDirect Journals</source><creator>Grajkowski, Andrzej ; Cawrse, Brian M. ; Takahashi, Mayumi ; Beaucage, Serge L.</creator><creatorcontrib>Grajkowski, Andrzej ; Cawrse, Brian M. ; Takahashi, Mayumi ; Beaucage, Serge L. ; Oak Ridge Institute for Science and Education (ORISE), Oak Ridge, TN (United States)</creatorcontrib><description>Here, to facilitate the solid-phase purification of synthetic DNA sequences, a riboside phosphoramidite, carrying a 5-O-capture linker and a 2-O-silyl ether protecting group, is incorporated into a DNA sequence during its last solid-phase synthesis cycle. After deprotection and release of the DNA sequence from the synthesis support, the sequence is then covalently linked to a capture support to enable the removal of shorter unbound DNA sequences by simply washing these off the support. The solid-phase purified DNA sequence is then released from the capture support, through an innovative intramolecular cyclodeesterification of its terminal riboside ethyl phosphate triester entity and is isolated in a yield of 94% while displaying an exquisite purity of 97%.</description><identifier>ISSN: 0040-4039</identifier><identifier>EISSN: 1873-3581</identifier><language>eng</language><publisher>United States: Elsevier</publisher><subject>BASIC BIOLOGICAL SCIENCES ; capture support ; ethyl phosphate triester ; intramolecular cyclodeesterification ; riboside phosphoramidite ; solid-phase purification ; solid-phase synthesis ; synthetic DNA sequences</subject><ispartof>Tetrahedron letters, 2022-08, Vol.106</ispartof><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>230,314,777,781,882</link.rule.ids><backlink>$$Uhttps://www.osti.gov/servlets/purl/1981776$$D View this record in Osti.gov$$Hfree_for_read</backlink></links><search><creatorcontrib>Grajkowski, Andrzej</creatorcontrib><creatorcontrib>Cawrse, Brian M.</creatorcontrib><creatorcontrib>Takahashi, Mayumi</creatorcontrib><creatorcontrib>Beaucage, Serge L.</creatorcontrib><creatorcontrib>Oak Ridge Institute for Science and Education (ORISE), Oak Ridge, TN (United States)</creatorcontrib><title>An improved process for the release of synthetic DNA sequences from a solid-phase capture support</title><title>Tetrahedron letters</title><description>Here, to facilitate the solid-phase purification of synthetic DNA sequences, a riboside phosphoramidite, carrying a 5-O-capture linker and a 2-O-silyl ether protecting group, is incorporated into a DNA sequence during its last solid-phase synthesis cycle. After deprotection and release of the DNA sequence from the synthesis support, the sequence is then covalently linked to a capture support to enable the removal of shorter unbound DNA sequences by simply washing these off the support. The solid-phase purified DNA sequence is then released from the capture support, through an innovative intramolecular cyclodeesterification of its terminal riboside ethyl phosphate triester entity and is isolated in a yield of 94% while displaying an exquisite purity of 97%.</description><subject>BASIC BIOLOGICAL SCIENCES</subject><subject>capture support</subject><subject>ethyl phosphate triester</subject><subject>intramolecular cyclodeesterification</subject><subject>riboside phosphoramidite</subject><subject>solid-phase purification</subject><subject>solid-phase synthesis</subject><subject>synthetic DNA sequences</subject><issn>0040-4039</issn><issn>1873-3581</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2022</creationdate><recordtype>article</recordtype><recordid>eNqNyksKwjAUheEgCtbHHi7OCymtbTosPnDkyLmE9JZG2iTmpoK7N4IL8Ex-OHwzlmSiytN8L7I5SzgveFrwvF6yFdGDx5WCJ0w2BvTovH1hCzEKiaCzHkKP4HFASQi2A3qb-ASt4HhtgPA5oYkWOm9HkEB20G3q-q9W0oXJI9DknPVhwxadHAi3v67Z7ny6HS6ppaDvpHRA1StrDKpwz2qRVVWZ_4U-usNGiQ</recordid><startdate>20220812</startdate><enddate>20220812</enddate><creator>Grajkowski, Andrzej</creator><creator>Cawrse, Brian M.</creator><creator>Takahashi, Mayumi</creator><creator>Beaucage, Serge L.</creator><general>Elsevier</general><scope>OIOZB</scope><scope>OTOTI</scope></search><sort><creationdate>20220812</creationdate><title>An improved process for the release of synthetic DNA sequences from a solid-phase capture support</title><author>Grajkowski, Andrzej ; Cawrse, Brian M. ; Takahashi, Mayumi ; Beaucage, Serge L.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-osti_scitechconnect_19817763</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2022</creationdate><topic>BASIC BIOLOGICAL SCIENCES</topic><topic>capture support</topic><topic>ethyl phosphate triester</topic><topic>intramolecular cyclodeesterification</topic><topic>riboside phosphoramidite</topic><topic>solid-phase purification</topic><topic>solid-phase synthesis</topic><topic>synthetic DNA sequences</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Grajkowski, Andrzej</creatorcontrib><creatorcontrib>Cawrse, Brian M.</creatorcontrib><creatorcontrib>Takahashi, Mayumi</creatorcontrib><creatorcontrib>Beaucage, Serge L.</creatorcontrib><creatorcontrib>Oak Ridge Institute for Science and Education (ORISE), Oak Ridge, TN (United States)</creatorcontrib><collection>OSTI.GOV - Hybrid</collection><collection>OSTI.GOV</collection><jtitle>Tetrahedron letters</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Grajkowski, Andrzej</au><au>Cawrse, Brian M.</au><au>Takahashi, Mayumi</au><au>Beaucage, Serge L.</au><aucorp>Oak Ridge Institute for Science and Education (ORISE), Oak Ridge, TN (United States)</aucorp><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>An improved process for the release of synthetic DNA sequences from a solid-phase capture support</atitle><jtitle>Tetrahedron letters</jtitle><date>2022-08-12</date><risdate>2022</risdate><volume>106</volume><issn>0040-4039</issn><eissn>1873-3581</eissn><abstract>Here, to facilitate the solid-phase purification of synthetic DNA sequences, a riboside phosphoramidite, carrying a 5-O-capture linker and a 2-O-silyl ether protecting group, is incorporated into a DNA sequence during its last solid-phase synthesis cycle. After deprotection and release of the DNA sequence from the synthesis support, the sequence is then covalently linked to a capture support to enable the removal of shorter unbound DNA sequences by simply washing these off the support. The solid-phase purified DNA sequence is then released from the capture support, through an innovative intramolecular cyclodeesterification of its terminal riboside ethyl phosphate triester entity and is isolated in a yield of 94% while displaying an exquisite purity of 97%.</abstract><cop>United States</cop><pub>Elsevier</pub><oa>free_for_read</oa></addata></record>
fulltext fulltext
identifier ISSN: 0040-4039
ispartof Tetrahedron letters, 2022-08, Vol.106
issn 0040-4039
1873-3581
language eng
recordid cdi_osti_scitechconnect_1981776
source Elsevier ScienceDirect Journals
subjects BASIC BIOLOGICAL SCIENCES
capture support
ethyl phosphate triester
intramolecular cyclodeesterification
riboside phosphoramidite
solid-phase purification
solid-phase synthesis
synthetic DNA sequences
title An improved process for the release of synthetic DNA sequences from a solid-phase capture support
url https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-17T21%3A55%3A38IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-osti&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=An%20improved%20process%20for%20the%20release%20of%20synthetic%20DNA%20sequences%20from%20a%20solid-phase%20capture%20support&rft.jtitle=Tetrahedron%20letters&rft.au=Grajkowski,%20Andrzej&rft.aucorp=Oak%20Ridge%20Institute%20for%20Science%20and%20Education%20(ORISE),%20Oak%20Ridge,%20TN%20(United%20States)&rft.date=2022-08-12&rft.volume=106&rft.issn=0040-4039&rft.eissn=1873-3581&rft_id=info:doi/&rft_dat=%3Costi%3E1981776%3C/osti%3E%3Curl%3E%3C/url%3E&disable_directlink=true&sfx.directlink=off&sfx.report_link=0&rft_id=info:oai/&rft_id=info:pmid/&rfr_iscdi=true