Release of DNA oligonucleotides and their conjugates from controlled-pore glass under thermolytic conditions.
Identifieur interne : 002054 ( PubMed/Corpus ); précédent : 002053; suivant : 002055Release of DNA oligonucleotides and their conjugates from controlled-pore glass under thermolytic conditions.
Auteurs : Andrzej Grajkowski ; Jacek Cie Lak ; Scott Norris ; Dar N I. Freedberg ; Jon S. Kauffman ; Robert J. Duff ; Serge L. BeaucageSource :
- Current protocols in nucleic acid chemistry [ 1934-9289 ] ; 2008.
English descriptors
- KwdEn :
- MESH :
- chemical , chemical synthesis : Oligodeoxyribonucleotides.
- chemical , chemistry : Oligodeoxyribonucleotides.
- chemical : Cross-Linking Reagents, Ligands.
- Glass, Hot Temperature, Methods, Surface Properties.
Abstract
The sequential functionalization of long-chain alkylamine controlled-pore glass (CPG) with a 3-hydroxypropyl-(2-cyanoethyl)thiophosphoryl linker and a dinucleoside phosphorotetrazolide leads to a uniquely engineered support for solid-phase synthesis. Unlike conventional succinylated-CPG supports, this support is designed to allow oligonucleotide deprotection and elimination of deprotection side-products to proceed without release of the oligonucleotide. When needed, the DNA oligonucleotide can be thermolytically released in 2 hr under essentially neutral conditions. The modified CPG support has been successfully employed in the synthesis of both native and fully phosphorothioated DNA 20-mers. On the basis of reversed-phase HPLC and electrophoretic analyses, the purity of the released oligonucleotides is comparable to that of identical oligonucleotides synthesized from succinylated-CPG supports, in terms of both shorter-than-full-length oligonucleotide contaminants and overall yields. The detailed preparation of DNA oligonucleotides conjugated with exemplary reporter or functional groups, either at the 3'-terminus or at both 3'- and 5'-termini, is also described.
DOI: 10.1002/0471142700.nc0317s35
PubMed: 19085983
Links to Exploration step
pubmed:19085983Le document en format XML
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Freedberg</name></author><author><name sortKey="Kauffman, Jon S" sort="Kauffman, Jon S" uniqKey="Kauffman J" first="Jon S" last="Kauffman">Jon S. Kauffman</name></author><author><name sortKey="Duff, Robert J" sort="Duff, Robert J" uniqKey="Duff R" first="Robert J" last="Duff">Robert J. Duff</name></author><author><name sortKey="Beaucage, Serge L" sort="Beaucage, Serge L" uniqKey="Beaucage S" first="Serge L" last="Beaucage">Serge L. Beaucage</name></author></titleStmt><publicationStmt><idno type="wicri:source">PubMed</idno><date when="2008">2008</date><idno type="RBID">pubmed:19085983</idno><idno type="pmid">19085983</idno><idno type="doi">10.1002/0471142700.nc0317s35</idno><idno type="wicri:Area/PubMed/Corpus">002054</idno><idno type="wicri:explorRef" wicri:stream="PubMed" wicri:step="Corpus" wicri:corpus="PubMed">002054</idno></publicationStmt><sourceDesc><biblStruct><analytic><title xml:lang="en">Release of DNA oligonucleotides and their conjugates from controlled-pore glass under thermolytic conditions.</title><author><name sortKey="Grajkowski, Andrzej" sort="Grajkowski, Andrzej" uniqKey="Grajkowski A" first="Andrzej" last="Grajkowski">Andrzej Grajkowski</name><affiliation><nlm:affiliation>Division of Therapeutic Proteins, Center for Drug Evaluation and Research, Food and Drug Administration, Bethesda, Maryland, USA.</nlm:affiliation></affiliation></author><author><name sortKey="Cie Lak, Jacek" sort="Cie Lak, Jacek" uniqKey="Cie Lak J" first="Jacek" last="Cie Lak">Jacek Cie Lak</name></author><author><name sortKey="Norris, Scott" sort="Norris, Scott" uniqKey="Norris S" first="Scott" last="Norris">Scott Norris</name></author><author><name sortKey="Freedberg, Dar N I" sort="Freedberg, Dar N I" uniqKey="Freedberg D" first="Dar N I" last="Freedberg">Dar N I. Freedberg</name></author><author><name sortKey="Kauffman, Jon S" sort="Kauffman, Jon S" uniqKey="Kauffman J" first="Jon S" last="Kauffman">Jon S. Kauffman</name></author><author><name sortKey="Duff, Robert J" sort="Duff, Robert J" uniqKey="Duff R" first="Robert J" last="Duff">Robert J. Duff</name></author><author><name sortKey="Beaucage, Serge L" sort="Beaucage, Serge L" uniqKey="Beaucage S" first="Serge L" last="Beaucage">Serge L. Beaucage</name></author></analytic><series><title level="j">Current protocols in nucleic acid chemistry</title><idno type="eISSN">1934-9289</idno><imprint><date when="2008" type="published">2008</date></imprint></series></biblStruct></sourceDesc></fileDesc><profileDesc><textClass><keywords scheme="KwdEn" xml:lang="en"><term>Cross-Linking Reagents</term><term>Glass</term><term>Hot Temperature</term><term>Ligands</term><term>Methods</term><term>Oligodeoxyribonucleotides (chemical synthesis)</term><term>Oligodeoxyribonucleotides (chemistry)</term><term>Surface Properties</term></keywords><keywords scheme="MESH" type="chemical" qualifier="chemical synthesis" xml:lang="en"><term>Oligodeoxyribonucleotides</term></keywords><keywords scheme="MESH" type="chemical" qualifier="chemistry" xml:lang="en"><term>Oligodeoxyribonucleotides</term></keywords><keywords scheme="MESH" type="chemical" xml:lang="en"><term>Cross-Linking Reagents</term><term>Ligands</term></keywords><keywords scheme="MESH" xml:lang="en"><term>Glass</term><term>Hot Temperature</term><term>Methods</term><term>Surface Properties</term></keywords></textClass></profileDesc></teiHeader><front><div type="abstract" xml:lang="en">The sequential functionalization of long-chain alkylamine controlled-pore glass (CPG) with a 3-hydroxypropyl-(2-cyanoethyl)thiophosphoryl linker and a dinucleoside phosphorotetrazolide leads to a uniquely engineered support for solid-phase synthesis. Unlike conventional succinylated-CPG supports, this support is designed to allow oligonucleotide deprotection and elimination of deprotection side-products to proceed without release of the oligonucleotide. When needed, the DNA oligonucleotide can be thermolytically released in 2 hr under essentially neutral conditions. The modified CPG support has been successfully employed in the synthesis of both native and fully phosphorothioated DNA 20-mers. On the basis of reversed-phase HPLC and electrophoretic analyses, the purity of the released oligonucleotides is comparable to that of identical oligonucleotides synthesized from succinylated-CPG supports, in terms of both shorter-than-full-length oligonucleotide contaminants and overall yields. The detailed preparation of DNA oligonucleotides conjugated with exemplary reporter or functional groups, either at the 3'-terminus or at both 3'- and 5'-termini, is also described.</div></front></TEI><pubmed><MedlineCitation Status="MEDLINE" Owner="NLM"><PMID Version="1">19085983</PMID><DateCompleted><Year>2009</Year><Month>01</Month><Day>22</Day></DateCompleted><DateRevised><Year>2016</Year><Month>10</Month><Day>21</Day></DateRevised><Article PubModel="Print"><Journal><ISSN IssnType="Electronic">1934-9289</ISSN><JournalIssue CitedMedium="Internet"><Volume>Chapter 3</Volume><PubDate><Year>2008</Year><Month>Dec</Month></PubDate></JournalIssue><Title>Current protocols in nucleic acid chemistry</Title><ISOAbbreviation>Curr Protoc Nucleic Acid Chem</ISOAbbreviation></Journal><ArticleTitle>Release of DNA oligonucleotides and their conjugates from controlled-pore glass under thermolytic conditions.</ArticleTitle><Pagination><MedlinePgn>Unit 3.17</MedlinePgn></Pagination><ELocationID EIdType="doi" ValidYN="Y">10.1002/0471142700.nc0317s35</ELocationID><Abstract><AbstractText>The sequential functionalization of long-chain alkylamine controlled-pore glass (CPG) with a 3-hydroxypropyl-(2-cyanoethyl)thiophosphoryl linker and a dinucleoside phosphorotetrazolide leads to a uniquely engineered support for solid-phase synthesis. Unlike conventional succinylated-CPG supports, this support is designed to allow oligonucleotide deprotection and elimination of deprotection side-products to proceed without release of the oligonucleotide. When needed, the DNA oligonucleotide can be thermolytically released in 2 hr under essentially neutral conditions. The modified CPG support has been successfully employed in the synthesis of both native and fully phosphorothioated DNA 20-mers. On the basis of reversed-phase HPLC and electrophoretic analyses, the purity of the released oligonucleotides is comparable to that of identical oligonucleotides synthesized from succinylated-CPG supports, in terms of both shorter-than-full-length oligonucleotide contaminants and overall yields. The detailed preparation of DNA oligonucleotides conjugated with exemplary reporter or functional groups, either at the 3'-terminus or at both 3'- and 5'-termini, is also described.</AbstractText><CopyrightInformation>Copyright 2008 by John Wiley & Sons, Inc.</CopyrightInformation></Abstract><AuthorList CompleteYN="Y"><Author ValidYN="Y"><LastName>Grajkowski</LastName><ForeName>Andrzej</ForeName><Initials>A</Initials><AffiliationInfo><Affiliation>Division of Therapeutic Proteins, Center for Drug Evaluation and Research, Food and Drug Administration, Bethesda, Maryland, USA.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Cieślak</LastName><ForeName>Jacek</ForeName><Initials>J</Initials></Author><Author ValidYN="Y"><LastName>Norris</LastName><ForeName>Scott</ForeName><Initials>S</Initials></Author><Author ValidYN="Y"><LastName>Freedberg</LastName><ForeName>Darón I</ForeName><Initials>DI</Initials></Author><Author ValidYN="Y"><LastName>Kauffman</LastName><ForeName>Jon S</ForeName><Initials>JS</Initials></Author><Author ValidYN="Y"><LastName>Duff</LastName><ForeName>Robert J</ForeName><Initials>RJ</Initials></Author><Author ValidYN="Y"><LastName>Beaucage</LastName><ForeName>Serge L</ForeName><Initials>SL</Initials></Author></AuthorList><Language>eng</Language><PublicationTypeList><PublicationType UI="D016428">Journal Article</PublicationType></PublicationTypeList></Article><MedlineJournalInfo><Country>United States</Country><MedlineTA>Curr Protoc Nucleic Acid Chem</MedlineTA><NlmUniqueID>101287865</NlmUniqueID><ISSNLinking>1934-9270</ISSNLinking></MedlineJournalInfo><ChemicalList><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance UI="D003432">Cross-Linking Reagents</NameOfSubstance></Chemical><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance UI="D008024">Ligands</NameOfSubstance></Chemical><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance UI="D009838">Oligodeoxyribonucleotides</NameOfSubstance></Chemical></ChemicalList><CitationSubset>IM</CitationSubset><MeshHeadingList><MeshHeading><DescriptorName UI="D003432" MajorTopicYN="N">Cross-Linking Reagents</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D005898" MajorTopicYN="N">Glass</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D006358" MajorTopicYN="N">Hot Temperature</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D008024" MajorTopicYN="N">Ligands</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D008722" MajorTopicYN="N">Methods</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D009838" MajorTopicYN="N">Oligodeoxyribonucleotides</DescriptorName><QualifierName UI="Q000138" MajorTopicYN="Y">chemical synthesis</QualifierName><QualifierName UI="Q000737" MajorTopicYN="N">chemistry</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D013499" MajorTopicYN="N">Surface Properties</DescriptorName></MeshHeading></MeshHeadingList></MedlineCitation><PubmedData><History><PubMedPubDate PubStatus="entrez"><Year>2008</Year><Month>12</Month><Day>17</Day><Hour>9</Hour><Minute>0</Minute></PubMedPubDate><PubMedPubDate PubStatus="pubmed"><Year>2008</Year><Month>12</Month><Day>17</Day><Hour>9</Hour><Minute>0</Minute></PubMedPubDate><PubMedPubDate PubStatus="medline"><Year>2009</Year><Month>1</Month><Day>23</Day><Hour>9</Hour><Minute>0</Minute></PubMedPubDate></History><PublicationStatus>ppublish</PublicationStatus><ArticleIdList><ArticleId IdType="pubmed">19085983</ArticleId><ArticleId IdType="doi">10.1002/0471142700.nc0317s35</ArticleId></ArticleIdList></PubmedData></pubmed></record>Pour manipuler ce document sous Unix (Dilib)
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