An improved CPG support for the synthesis of 3'-amine-tailed oligonucleotides

A new controlled-pore glass (CPG) support is described that allows for the direct synthesis of oligonucleotides bearing a 3'-aminohexyl tail. This solid support (AH-CPG) exhibits superior performance as compared to a commercially available 3'-amine CPG. The AH-CPG is prepared from 6-aminoh...

Full description

Saved in:
Bibliographic Details
Published in:Bioconjugate chemistry 1992-01, Vol.3 (1), p.85-87
Main Authors: Petrie, Charles R., Reed, Michael W., Adams, A. David, Meyer, Rich B.
Format: Article
Language:English
Subjects:
Acridines - chemistry
Biochemical Research Methods
Biochemistry & Molecular Biology
Biological and medical sciences
Biotechnology
Chemistry
Chemistry, Multidisciplinary
Chemistry, Organic
Chromatography, High Pressure Liquid
Fundamental and applied biological sciences. Psychology
Genetic technics
Glass
Life Sciences & Biomedicine
Methods. Procedures. Technologies
Oligonucleotides - chemical synthesis
Physical Sciences
Science & Technology
Citations: 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-a449t-40888df70b5d4ce7b5943f2ff5103df7b69171d3b26823808dc0513ab0bfd9ff3
cites
container_end_page 87
container_issue 1
container_start_page 85
container_title Bioconjugate chemistry
container_volume 3
creator Petrie, Charles R.
Reed, Michael W.
Adams, A. David
Meyer, Rich B.
description A new controlled-pore glass (CPG) support is described that allows for the direct synthesis of oligonucleotides bearing a 3'-aminohexyl tail. This solid support (AH-CPG) exhibits superior performance as compared to a commercially available 3'-amine CPG. The AH-CPG is prepared from 6-aminohexan-1-ol with a unique protecting group for the amine that also functions as the site of attachment to the CPG. A 3'-amine-tailed oligodeoxynucleotide (ODN) was prepared from this support using standard phosphoramidite coupling and deprotection conditions. The 3'-amine-tailed ODN was subsequently modified with an acridinylpropionic acid tetrafluorophenyl ester. Facile synthesis of the AH-CPG and the stability of the deprotected product makes this functionalized solid support especially useful for preparation of oligonucleotides bearing 3'-amine tails and other modifications.
doi_str_mv 10.1021/bc00013a014
format article
fullrecord <record><control><sourceid>proquest_acs_j</sourceid><recordid>TN_cdi_acs_journals_10_1021_bc00013a014</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>73043588</sourcerecordid><originalsourceid>FETCH-LOGICAL-a449t-40888df70b5d4ce7b5943f2ff5103df7b69171d3b26823808dc0513ab0bfd9ff3</originalsourceid><addsrcrecordid>eNqNkU1v1DAQhi0EKqVw4oyUA6IHFPBXEvu4SmEXaSsqUQTiYtmODS6JvbUdoP8el6y2HDhwmtHMM1_vAPAUwVcIYvRaaQghIhIieg8cowbDmjKE7xcfUlIjBvFD8Cilq4JxxPAROEItanlDj8H5yldu2sXwwwxVf7Gu0rzbhZgrG2KVv5kq3fhikktVsBU5reXkvKmzdGMpCKP7GvysRxOyG0x6DB5YOSbzZG9PwMe3by77Tb19v37Xr7a1pJTnmkLG2GA7qJqBatOphlNisbUNgqTEVctRhwaicMswYZANGjblQAWVHbi15AS8WPqWxa9nk7KYXNJmHKU3YU6iI-XwhrECvlxAHUNK0Vixi26S8UYgKG7FE3-JV-hn-7azmsxwxy5qlfzzfV4mLUcbpdcuHTBKaMf_DGUL9tOoYJN2xmtzoFaIc7w5K3-4HUx7l2V2wfdh9vlu3_8pLXS90C5l8-uAyfhdtB3pGnF58UGcb7Zn5NP6s_hS-NOFlzqJqzBHX570TyV-A-dKsi4</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>73043588</pqid></control><display><type>article</type><title>An improved CPG support for the synthesis of 3'-amine-tailed oligonucleotides</title><source>Web of Science - Science Citation Index Expanded - 1992&lt;img src="https://exlibris-pub.s3.amazonaws.com/fromwos-v2.jpg" /&gt;</source><source>ACS CRKN Legacy Archives</source><creator>Petrie, Charles R. ; Reed, Michael W. ; Adams, A. David ; Meyer, Rich B.</creator><creatorcontrib>Petrie, Charles R. ; Reed, Michael W. ; Adams, A. David ; Meyer, Rich B.</creatorcontrib><description>A new controlled-pore glass (CPG) support is described that allows for the direct synthesis of oligonucleotides bearing a 3'-aminohexyl tail. This solid support (AH-CPG) exhibits superior performance as compared to a commercially available 3'-amine CPG. The AH-CPG is prepared from 6-aminohexan-1-ol with a unique protecting group for the amine that also functions as the site of attachment to the CPG. A 3'-amine-tailed oligodeoxynucleotide (ODN) was prepared from this support using standard phosphoramidite coupling and deprotection conditions. The 3'-amine-tailed ODN was subsequently modified with an acridinylpropionic acid tetrafluorophenyl ester. Facile synthesis of the AH-CPG and the stability of the deprotected product makes this functionalized solid support especially useful for preparation of oligonucleotides bearing 3'-amine tails and other modifications.</description><identifier>ISSN: 1043-1802</identifier><identifier>EISSN: 1520-4812</identifier><identifier>DOI: 10.1021/bc00013a014</identifier><identifier>PMID: 1616954</identifier><language>eng</language><publisher>WASHINGTON: American Chemical Society</publisher><subject>Acridines - chemistry ; Biochemical Research Methods ; Biochemistry &amp; Molecular Biology ; Biological and medical sciences ; Biotechnology ; Chemistry ; Chemistry, Multidisciplinary ; Chemistry, Organic ; Chromatography, High Pressure Liquid ; Fundamental and applied biological sciences. Psychology ; Genetic technics ; Glass ; Life Sciences &amp; Biomedicine ; Methods. Procedures. Technologies ; Oligonucleotides - chemical synthesis ; Physical Sciences ; Science &amp; Technology</subject><ispartof>Bioconjugate chemistry, 1992-01, Vol.3 (1), p.85-87</ispartof><rights>1993 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>true</woscitedreferencessubscribed><woscitedreferencescount>41</woscitedreferencescount><woscitedreferencesoriginalsourcerecordid>wosA1992HD18200014</woscitedreferencesoriginalsourcerecordid><citedby>FETCH-LOGICAL-a449t-40888df70b5d4ce7b5943f2ff5103df7b69171d3b26823808dc0513ab0bfd9ff3</citedby></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://pubs.acs.org/doi/pdf/10.1021/bc00013a014$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/bc00013a014$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>315,786,790,27097,27225,27957,27958,57121,57171</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&amp;idt=4347988$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/1616954$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Petrie, Charles R.</creatorcontrib><creatorcontrib>Reed, Michael W.</creatorcontrib><creatorcontrib>Adams, A. David</creatorcontrib><creatorcontrib>Meyer, Rich B.</creatorcontrib><title>An improved CPG support for the synthesis of 3'-amine-tailed oligonucleotides</title><title>Bioconjugate chemistry</title><addtitle>BIOCONJUGATE CHEM</addtitle><addtitle>Bioconjugate Chem</addtitle><description>A new controlled-pore glass (CPG) support is described that allows for the direct synthesis of oligonucleotides bearing a 3'-aminohexyl tail. This solid support (AH-CPG) exhibits superior performance as compared to a commercially available 3'-amine CPG. The AH-CPG is prepared from 6-aminohexan-1-ol with a unique protecting group for the amine that also functions as the site of attachment to the CPG. A 3'-amine-tailed oligodeoxynucleotide (ODN) was prepared from this support using standard phosphoramidite coupling and deprotection conditions. The 3'-amine-tailed ODN was subsequently modified with an acridinylpropionic acid tetrafluorophenyl ester. Facile synthesis of the AH-CPG and the stability of the deprotected product makes this functionalized solid support especially useful for preparation of oligonucleotides bearing 3'-amine tails and other modifications.</description><subject>Acridines - chemistry</subject><subject>Biochemical Research Methods</subject><subject>Biochemistry &amp; Molecular Biology</subject><subject>Biological and medical sciences</subject><subject>Biotechnology</subject><subject>Chemistry</subject><subject>Chemistry, Multidisciplinary</subject><subject>Chemistry, Organic</subject><subject>Chromatography, High Pressure Liquid</subject><subject>Fundamental and applied biological sciences. Psychology</subject><subject>Genetic technics</subject><subject>Glass</subject><subject>Life Sciences &amp; Biomedicine</subject><subject>Methods. Procedures. Technologies</subject><subject>Oligonucleotides - chemical synthesis</subject><subject>Physical Sciences</subject><subject>Science &amp; Technology</subject><issn>1043-1802</issn><issn>1520-4812</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>1992</creationdate><recordtype>article</recordtype><sourceid>EZCTM</sourceid><recordid>eNqNkU1v1DAQhi0EKqVw4oyUA6IHFPBXEvu4SmEXaSsqUQTiYtmODS6JvbUdoP8el6y2HDhwmtHMM1_vAPAUwVcIYvRaaQghIhIieg8cowbDmjKE7xcfUlIjBvFD8Cilq4JxxPAROEItanlDj8H5yldu2sXwwwxVf7Gu0rzbhZgrG2KVv5kq3fhikktVsBU5reXkvKmzdGMpCKP7GvysRxOyG0x6DB5YOSbzZG9PwMe3by77Tb19v37Xr7a1pJTnmkLG2GA7qJqBatOphlNisbUNgqTEVctRhwaicMswYZANGjblQAWVHbi15AS8WPqWxa9nk7KYXNJmHKU3YU6iI-XwhrECvlxAHUNK0Vixi26S8UYgKG7FE3-JV-hn-7azmsxwxy5qlfzzfV4mLUcbpdcuHTBKaMf_DGUL9tOoYJN2xmtzoFaIc7w5K3-4HUx7l2V2wfdh9vlu3_8pLXS90C5l8-uAyfhdtB3pGnF58UGcb7Zn5NP6s_hS-NOFlzqJqzBHX570TyV-A-dKsi4</recordid><startdate>19920101</startdate><enddate>19920101</enddate><creator>Petrie, Charles R.</creator><creator>Reed, Michael W.</creator><creator>Adams, A. David</creator><creator>Meyer, Rich B.</creator><general>American Chemical Society</general><general>Amer Chemical Soc</general><scope>BSCLL</scope><scope>BLEPL</scope><scope>DTL</scope><scope>EZCTM</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>19920101</creationdate><title>An improved CPG support for the synthesis of 3'-amine-tailed oligonucleotides</title><author>Petrie, Charles R. ; Reed, Michael W. ; Adams, A. David ; Meyer, Rich B.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a449t-40888df70b5d4ce7b5943f2ff5103df7b69171d3b26823808dc0513ab0bfd9ff3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>1992</creationdate><topic>Acridines - chemistry</topic><topic>Biochemical Research Methods</topic><topic>Biochemistry &amp; Molecular Biology</topic><topic>Biological and medical sciences</topic><topic>Biotechnology</topic><topic>Chemistry</topic><topic>Chemistry, Multidisciplinary</topic><topic>Chemistry, Organic</topic><topic>Chromatography, High Pressure Liquid</topic><topic>Fundamental and applied biological sciences. Psychology</topic><topic>Genetic technics</topic><topic>Glass</topic><topic>Life Sciences &amp; Biomedicine</topic><topic>Methods. Procedures. Technologies</topic><topic>Oligonucleotides - chemical synthesis</topic><topic>Physical Sciences</topic><topic>Science &amp; Technology</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Petrie, Charles R.</creatorcontrib><creatorcontrib>Reed, Michael W.</creatorcontrib><creatorcontrib>Adams, A. David</creatorcontrib><creatorcontrib>Meyer, Rich B.</creatorcontrib><collection>Istex</collection><collection>Web of Science Core Collection</collection><collection>Science Citation Index Expanded</collection><collection>Web of Science - Science Citation Index Expanded - 1992</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>Bioconjugate chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Petrie, Charles R.</au><au>Reed, Michael W.</au><au>Adams, A. David</au><au>Meyer, Rich B.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>An improved CPG support for the synthesis of 3'-amine-tailed oligonucleotides</atitle><jtitle>Bioconjugate chemistry</jtitle><stitle>BIOCONJUGATE CHEM</stitle><addtitle>Bioconjugate Chem</addtitle><date>1992-01-01</date><risdate>1992</risdate><volume>3</volume><issue>1</issue><spage>85</spage><epage>87</epage><pages>85-87</pages><issn>1043-1802</issn><eissn>1520-4812</eissn><notes>istex:3B1054A0D94D36FFBD0DAEBD9F8E6875A97FD2BB</notes><notes>ark:/67375/TPS-MHLD3WGX-Z</notes><notes>Medline</notes><notes>NIH RePORTER</notes><notes>ObjectType-Article-1</notes><notes>SourceType-Scholarly Journals-1</notes><notes>ObjectType-Feature-2</notes><notes>content type line 23</notes><abstract>A new controlled-pore glass (CPG) support is described that allows for the direct synthesis of oligonucleotides bearing a 3'-aminohexyl tail. This solid support (AH-CPG) exhibits superior performance as compared to a commercially available 3'-amine CPG. The AH-CPG is prepared from 6-aminohexan-1-ol with a unique protecting group for the amine that also functions as the site of attachment to the CPG. A 3'-amine-tailed oligodeoxynucleotide (ODN) was prepared from this support using standard phosphoramidite coupling and deprotection conditions. The 3'-amine-tailed ODN was subsequently modified with an acridinylpropionic acid tetrafluorophenyl ester. Facile synthesis of the AH-CPG and the stability of the deprotected product makes this functionalized solid support especially useful for preparation of oligonucleotides bearing 3'-amine tails and other modifications.</abstract><cop>WASHINGTON</cop><pub>American Chemical Society</pub><pmid>1616954</pmid><doi>10.1021/bc00013a014</doi><tpages>3</tpages></addata></record>
fulltext fulltext
identifier ISSN: 1043-1802
ispartof Bioconjugate chemistry, 1992-01, Vol.3 (1), p.85-87
issn 1043-1802
1520-4812
language eng
recordid cdi_acs_journals_10_1021_bc00013a014
source Web of Science - Science Citation Index Expanded - 1992<img src="https://exlibris-pub.s3.amazonaws.com/fromwos-v2.jpg" />; ACS CRKN Legacy Archives
subjects Acridines - chemistry
Biochemical Research Methods
Biochemistry & Molecular Biology
Biological and medical sciences
Biotechnology
Chemistry
Chemistry, Multidisciplinary
Chemistry, Organic
Chromatography, High Pressure Liquid
Fundamental and applied biological sciences. Psychology
Genetic technics
Glass
Life Sciences & Biomedicine
Methods. Procedures. Technologies
Oligonucleotides - chemical synthesis
Physical Sciences
Science & Technology
title An improved CPG support for the synthesis of 3'-amine-tailed oligonucleotides
url http://sfxeu10.hosted.exlibrisgroup.com/loughborough?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2024-09-23T07%3A32%3A33IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-proquest_acs_j&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=An%20improved%20CPG%20support%20for%20the%20synthesis%20of%203'-amine-tailed%20oligonucleotides&rft.jtitle=Bioconjugate%20chemistry&rft.au=Petrie,%20Charles%20R.&rft.date=1992-01-01&rft.volume=3&rft.issue=1&rft.spage=85&rft.epage=87&rft.pages=85-87&rft.issn=1043-1802&rft.eissn=1520-4812&rft_id=info:doi/10.1021/bc00013a014&rft_dat=%3Cproquest_acs_j%3E73043588%3C/proquest_acs_j%3E%3Cgrp_id%3Ecdi_FETCH-LOGICAL-a449t-40888df70b5d4ce7b5943f2ff5103df7b69171d3b26823808dc0513ab0bfd9ff3%3C/grp_id%3E%3Coa%3E%3C/oa%3E%3Curl%3E%3C/url%3E&rft_id=info:oai/&rft_pqid=73043588&rft_id=info:pmid/1616954&rfr_iscdi=true