Versatile Linker Chemistry for Synthesis of 3‘-Modified DNA
Identifieur interne : 001410 ( Istex/Checkpoint ); précédent : 001409; suivant : 001411Versatile Linker Chemistry for Synthesis of 3‘-Modified DNA
Auteurs : Matthew H. Lyttle [États-Unis] ; Howard Adams [États-Unis] ; Derek Hudson [États-Unis] ; Ronald M. Cook [États-Unis]Source :
- Bioconjugate Chemistry [ 1043-1802 ] ; 1997.
Abstract
A general method is described for the solid phase supported synthesis of DNA containing 3‘-terminal phosphodiesters modified with linkers bearing either amino, thiol, or hydroxyl groups. These products are all made from a common intermediate, obtained by the reaction of trimellitic anhydride chloride with aminopropyl CPG. The anhydride-derivatized support was then reacted with three appropriate bifunctional spacers, giving DMT-protected hydroxyl solid supports bearing the masked functionality as an ester, amide, or thioester. DNA synthesis was then performed, followed by ammonia cleavage and deprotection, giving the hydroxyl-, amino-, or thiol-functionalized DNA 3‘-phosphate diesters, respectively. Test mononucleotides synthesized with each of the new supports were identical with control mononucleotides made with 5‘-immobilized nucleosides and alkylhydroxyl, alkylamino, and alkylthio phosphoramidites. The new supports were then used to prepare several 3‘-modified oligonucleotides, which were characterized by gel electrophoresis, HPLC, and MALDI mass spectroscopy. The amino- and thiol-functionalized DNAs were conjugated with chromophores, and purification of these products was facilitated by use of reversed phase cartridges.
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DOI: 10.1021/bc970010y
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<record><TEI wicri:istexFullTextTei="biblStruct"><teiHeader><fileDesc><titleStmt><title>Versatile Linker Chemistry for Synthesis of 3‘-Modified DNA</title><author><name sortKey="Lyttle, Matthew H" sort="Lyttle, Matthew H" uniqKey="Lyttle M" first="Matthew H." last="Lyttle">Matthew H. Lyttle</name></author><author><name sortKey="Adams, Howard" sort="Adams, Howard" uniqKey="Adams H" first="Howard" last="Adams">Howard Adams</name></author><author><name sortKey="Hudson, Derek" sort="Hudson, Derek" uniqKey="Hudson D" first="Derek" last="Hudson">Derek Hudson</name></author><author><name sortKey="Cook, Ronald M" sort="Cook, Ronald M" uniqKey="Cook R" first="Ronald M." last="Cook">Ronald M. Cook</name></author></titleStmt><publicationStmt><idno type="wicri:source">ISTEX</idno><idno type="RBID">ISTEX:043B6793E3CFD3D932BC3EBA736558D71CE3676E</idno><date when="1997" year="1997">1997</date><idno type="doi">10.1021/bc970010y</idno><idno type="url">https://api.istex.fr/ark:/67375/TPS-C0J97154-X/fulltext.pdf</idno><idno type="wicri:Area/Istex/Corpus">000A47</idno><idno type="wicri:explorRef" wicri:stream="Istex" wicri:step="Corpus" wicri:corpus="ISTEX">000A47</idno><idno type="wicri:Area/Istex/Curation">000A47</idno><idno type="wicri:Area/Istex/Checkpoint">001410</idno><idno type="wicri:explorRef" wicri:stream="Istex" wicri:step="Checkpoint">001410</idno></publicationStmt><sourceDesc><biblStruct><analytic><title level="a" type="main">Versatile Linker Chemistry for Synthesis of 3‘-Modified DNA</title><author><name sortKey="Lyttle, Matthew H" sort="Lyttle, Matthew H" uniqKey="Lyttle M" first="Matthew H." last="Lyttle">Matthew H. Lyttle</name><affiliation wicri:level="2"><country xml:lang="fr">États-Unis</country><placeName><region type="state">Californie</region></placeName><wicri:cityArea>Biosearch Technologies Inc., 40 Mark Drive, San Rafael</wicri:cityArea></affiliation><affiliation></affiliation></author><author><name sortKey="Adams, Howard" sort="Adams, Howard" uniqKey="Adams H" first="Howard" last="Adams">Howard Adams</name><affiliation wicri:level="2"><country xml:lang="fr">États-Unis</country><placeName><region type="state">Californie</region></placeName><wicri:cityArea>Biosearch Technologies Inc., 40 Mark Drive, San Rafael</wicri:cityArea></affiliation></author><author><name sortKey="Hudson, Derek" sort="Hudson, Derek" uniqKey="Hudson D" first="Derek" last="Hudson">Derek Hudson</name><affiliation wicri:level="2"><country xml:lang="fr">États-Unis</country><placeName><region type="state">Californie</region></placeName><wicri:cityArea>Biosearch Technologies Inc., 40 Mark Drive, San Rafael</wicri:cityArea></affiliation></author><author><name sortKey="Cook, Ronald M" sort="Cook, Ronald M" uniqKey="Cook R" first="Ronald M." last="Cook">Ronald M. Cook</name><affiliation wicri:level="2"><country xml:lang="fr">États-Unis</country><placeName><region type="state">Californie</region></placeName><wicri:cityArea>Biosearch Technologies Inc., 40 Mark Drive, San Rafael</wicri:cityArea></affiliation></author></analytic><monogr></monogr><series><title level="j" type="main">Bioconjugate Chemistry</title><title level="j" type="abbrev">Bioconjugate Chem.</title><idno type="ISSN">1043-1802</idno><idno type="eISSN">1520-4812</idno><imprint><publisher>American Chemical Society</publisher><date type="e-published">1997</date><date type="published">1997</date><biblScope unit="vol">8</biblScope><biblScope unit="issue">2</biblScope><biblScope unit="page" from="193">193</biblScope><biblScope unit="page" to="198">198</biblScope></imprint><idno type="ISSN">1043-1802</idno></series></biblStruct></sourceDesc><seriesStmt><idno type="ISSN">1043-1802</idno></seriesStmt></fileDesc><profileDesc><textClass></textClass></profileDesc></teiHeader><front><div type="abstract">A general method is described for the solid phase supported synthesis of DNA containing 3‘-terminal phosphodiesters modified with linkers bearing either amino, thiol, or hydroxyl groups. These products are all made from a common intermediate, obtained by the reaction of trimellitic anhydride chloride with aminopropyl CPG. The anhydride-derivatized support was then reacted with three appropriate bifunctional spacers, giving DMT-protected hydroxyl solid supports bearing the masked functionality as an ester, amide, or thioester. DNA synthesis was then performed, followed by ammonia cleavage and deprotection, giving the hydroxyl-, amino-, or thiol-functionalized DNA 3‘-phosphate diesters, respectively. Test mononucleotides synthesized with each of the new supports were identical with control mononucleotides made with 5‘-immobilized nucleosides and alkylhydroxyl, alkylamino, and alkylthio phosphoramidites. The new supports were then used to prepare several 3‘-modified oligonucleotides, which were characterized by gel electrophoresis, HPLC, and MALDI mass spectroscopy. The amino- and thiol-functionalized DNAs were conjugated with chromophores, and purification of these products was facilitated by use of reversed phase cartridges.</div></front></TEI><affiliations><list><country><li>États-Unis</li></country><region><li>Californie</li></region></list><tree><country name="États-Unis"><region name="Californie"><name sortKey="Lyttle, Matthew H" sort="Lyttle, Matthew H" uniqKey="Lyttle M" first="Matthew H." last="Lyttle">Matthew H. Lyttle</name></region><name sortKey="Adams, Howard" sort="Adams, Howard" uniqKey="Adams H" first="Howard" last="Adams">Howard Adams</name><name sortKey="Cook, Ronald M" sort="Cook, Ronald M" uniqKey="Cook R" first="Ronald M." last="Cook">Ronald M. Cook</name><name sortKey="Hudson, Derek" sort="Hudson, Derek" uniqKey="Hudson D" first="Derek" last="Hudson">Derek Hudson</name></country></tree></affiliations></record>Pour manipuler ce document sous Unix (Dilib)
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