Thermolytic release of covalently linked DNA oligonucleotides and their conjugates from controlled-pore glass at near neutral pH.
Identifieur interne : 001F48 ( PubMed/Checkpoint ); précédent : 001F47; suivant : 001F49Thermolytic release of covalently linked DNA oligonucleotides and their conjugates from controlled-pore glass at near neutral pH.
Auteurs : Andrzej Grajkowski [États-Unis] ; Jacek Cie Lak ; Jon S. Kauffman ; Robert J. Duff ; Scott Norris ; Dar N I. Freedberg ; Serge L. BeaucageSource :
- Bioconjugate chemistry [ 1520-4812 ] ; 2008.
Descripteurs français
- KwdFr :
- MESH :
English descriptors
- KwdEn :
- Amides (chemistry), Base Sequence, DNA (chemistry), DNA (genetics), Dinucleoside Phosphates (chemistry), Glass (chemistry), Hot Temperature, Hydrogen-Ion Concentration, Oligonucleotides (chemistry), Oligonucleotides (genetics), Phosphates (chemistry), Phosphoramides, Phosphoric Acids (chemistry), Porosity.
- MESH :
- chemical , chemistry : Amides, DNA, Dinucleoside Phosphates, Oligonucleotides, Phosphates, Phosphoric Acids.
- chemical , genetics : DNA, Oligonucleotides.
- chemistry : Glass.
- Base Sequence, Hot Temperature, Hydrogen-Ion Concentration, Phosphoramides, Porosity.
Abstract
The functionalization of long chain alkylamine controlled-pore glass (CPG) with a 3-hydroxypropyl-(2-cyanoethyl)thiophosphoryl linker and its conversion to the support 7 has led to the synthesis of DNA oligonucleotides and their 3'- or (3',5')-conjugates. Indeed, CPG support 7 has been successfully employed in the synthesis of both native and fully phosphorothioated DNA 20-mers. Unlike conventional succinylated CPG supports, this distinctively functionalized support allows oligonucleotide deprotection and removal of the deprotection side products to proceed without releasing the oligonucleotide into the aqueous milieu. When freed from deprotection side products, the DNA oligonucleotide is thermolytically released from the support within 2 h under nearly neutral conditions (pH 7.2, 90 degrees C). The quality of these oligonucleotides is comparable to that of identical oligonucleotides synthesized from succinylated CPG supports in terms of shorter than full length oligonucleotide contaminants and overall yields. The versatility of the thermolytic CPG support 7 is further demonstrated by the synthesis of a DNA oligonucleotide (20-mer) and its conjugation with an azido and alkynyl groups at both 5'-and 3'-termini, respectively. The functionality of the (3',5')-heteroconjugated oligonucleotide 18 is verified by its circularization to the DNA oligonucleotide 19 under "click" chemistry conditions.
DOI: 10.1021/bc800189e
PubMed: 18646834
Affiliations:
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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="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="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:18646834</idno><idno type="pmid">18646834</idno><idno type="doi">10.1021/bc800189e</idno><idno type="wicri:Area/PubMed/Corpus">002090</idno><idno type="wicri:explorRef" wicri:stream="PubMed" wicri:step="Corpus" wicri:corpus="PubMed">002090</idno><idno type="wicri:Area/PubMed/Curation">002090</idno><idno type="wicri:explorRef" wicri:stream="PubMed" wicri:step="Curation">002090</idno><idno type="wicri:Area/PubMed/Checkpoint">001F48</idno><idno type="wicri:explorRef" wicri:stream="Checkpoint" wicri:step="PubMed">001F48</idno></publicationStmt><sourceDesc><biblStruct><analytic><title xml:lang="en">Thermolytic release of covalently linked DNA oligonucleotides and their conjugates from controlled-pore glass at near neutral pH.</title><author><name sortKey="Grajkowski, Andrzej" sort="Grajkowski, Andrzej" uniqKey="Grajkowski A" first="Andrzej" last="Grajkowski">Andrzej Grajkowski</name><affiliation wicri:level="1"><nlm:affiliation>Division of Therapeutic Proteins, Center for Drug Evaluation and Research, Food and Drug Administration, 8800 Rockville Pike, Bethesda, Maryland 20892, USA.</nlm:affiliation><country xml:lang="fr">États-Unis</country><wicri:regionArea>Division of Therapeutic Proteins, Center for Drug Evaluation and Research, Food and Drug Administration, 8800 Rockville Pike, Bethesda, Maryland 20892</wicri:regionArea><wicri:noRegion>Maryland 20892</wicri:noRegion></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="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="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="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">Bioconjugate chemistry</title><idno type="eISSN">1520-4812</idno><imprint><date when="2008" type="published">2008</date></imprint></series></biblStruct></sourceDesc></fileDesc><profileDesc><textClass><keywords scheme="KwdEn" xml:lang="en"><term>Amides (chemistry)</term><term>Base Sequence</term><term>DNA (chemistry)</term><term>DNA (genetics)</term><term>Dinucleoside Phosphates (chemistry)</term><term>Glass (chemistry)</term><term>Hot Temperature</term><term>Hydrogen-Ion Concentration</term><term>Oligonucleotides (chemistry)</term><term>Oligonucleotides (genetics)</term><term>Phosphates (chemistry)</term><term>Phosphoramides</term><term>Phosphoric Acids (chemistry)</term><term>Porosity</term></keywords><keywords scheme="KwdFr" xml:lang="fr"><term>ADN ()</term><term>ADN (génétique)</term><term>Acides phosphoriques ()</term><term>Amides ()</term><term>Concentration en ions d'hydrogène</term><term>Dinucléoside phosphates ()</term><term>Oligonucléotides ()</term><term>Oligonucléotides (génétique)</term><term>Phosphates ()</term><term>Phosphoramides</term><term>Porosité</term><term>Séquence nucléotidique</term><term>Température élevée</term><term>Verre ()</term></keywords><keywords scheme="MESH" type="chemical" qualifier="chemistry" xml:lang="en"><term>Amides</term><term>DNA</term><term>Dinucleoside Phosphates</term><term>Oligonucleotides</term><term>Phosphates</term><term>Phosphoric Acids</term></keywords><keywords scheme="MESH" type="chemical" qualifier="genetics" xml:lang="en"><term>DNA</term><term>Oligonucleotides</term></keywords><keywords scheme="MESH" qualifier="chemistry" xml:lang="en"><term>Glass</term></keywords><keywords scheme="MESH" qualifier="génétique" xml:lang="fr"><term>ADN</term><term>Oligonucléotides</term></keywords><keywords scheme="MESH" xml:lang="en"><term>Base Sequence</term><term>Hot Temperature</term><term>Hydrogen-Ion Concentration</term><term>Phosphoramides</term><term>Porosity</term></keywords><keywords scheme="MESH" xml:lang="fr"><term>ADN</term><term>Acides phosphoriques</term><term>Amides</term><term>Concentration en ions d'hydrogène</term><term>Dinucléoside phosphates</term><term>Oligonucléotides</term><term>Phosphates</term><term>Phosphoramides</term><term>Porosité</term><term>Séquence nucléotidique</term><term>Température élevée</term><term>Verre</term></keywords></textClass></profileDesc></teiHeader><front><div type="abstract" xml:lang="en">The functionalization of long chain alkylamine controlled-pore glass (CPG) with a 3-hydroxypropyl-(2-cyanoethyl)thiophosphoryl linker and its conversion to the support 7 has led to the synthesis of DNA oligonucleotides and their 3'- or (3',5')-conjugates. Indeed, CPG support 7 has been successfully employed in the synthesis of both native and fully phosphorothioated DNA 20-mers. Unlike conventional succinylated CPG supports, this distinctively functionalized support allows oligonucleotide deprotection and removal of the deprotection side products to proceed without releasing the oligonucleotide into the aqueous milieu. When freed from deprotection side products, the DNA oligonucleotide is thermolytically released from the support within 2 h under nearly neutral conditions (pH 7.2, 90 degrees C). The quality of these oligonucleotides is comparable to that of identical oligonucleotides synthesized from succinylated CPG supports in terms of shorter than full length oligonucleotide contaminants and overall yields. The versatility of the thermolytic CPG support 7 is further demonstrated by the synthesis of a DNA oligonucleotide (20-mer) and its conjugation with an azido and alkynyl groups at both 5'-and 3'-termini, respectively. The functionality of the (3',5')-heteroconjugated oligonucleotide 18 is verified by its circularization to the DNA oligonucleotide 19 under "click" chemistry conditions.</div></front></TEI><pubmed><MedlineCitation Status="MEDLINE" Owner="NLM"><PMID Version="1">18646834</PMID><DateCompleted><Year>2008</Year><Month>10</Month><Day>21</Day></DateCompleted><DateRevised><Year>2012</Year><Month>11</Month><Day>15</Day></DateRevised><Article PubModel="Print-Electronic"><Journal><ISSN IssnType="Electronic">1520-4812</ISSN><JournalIssue CitedMedium="Internet"><Volume>19</Volume><Issue>8</Issue><PubDate><Year>2008</Year><Month>Aug</Month></PubDate></JournalIssue><Title>Bioconjugate chemistry</Title><ISOAbbreviation>Bioconjug. Chem.</ISOAbbreviation></Journal><ArticleTitle>Thermolytic release of covalently linked DNA oligonucleotides and their conjugates from controlled-pore glass at near neutral pH.</ArticleTitle><Pagination><MedlinePgn>1696-706</MedlinePgn></Pagination><ELocationID EIdType="doi" ValidYN="Y">10.1021/bc800189e</ELocationID><Abstract><AbstractText>The functionalization of long chain alkylamine controlled-pore glass (CPG) with a 3-hydroxypropyl-(2-cyanoethyl)thiophosphoryl linker and its conversion to the support 7 has led to the synthesis of DNA oligonucleotides and their 3'- or (3',5')-conjugates. Indeed, CPG support 7 has been successfully employed in the synthesis of both native and fully phosphorothioated DNA 20-mers. Unlike conventional succinylated CPG supports, this distinctively functionalized support allows oligonucleotide deprotection and removal of the deprotection side products to proceed without releasing the oligonucleotide into the aqueous milieu. When freed from deprotection side products, the DNA oligonucleotide is thermolytically released from the support within 2 h under nearly neutral conditions (pH 7.2, 90 degrees C). The quality of these oligonucleotides is comparable to that of identical oligonucleotides synthesized from succinylated CPG supports in terms of shorter than full length oligonucleotide contaminants and overall yields. The versatility of the thermolytic CPG support 7 is further demonstrated by the synthesis of a DNA oligonucleotide (20-mer) and its conjugation with an azido and alkynyl groups at both 5'-and 3'-termini, respectively. The functionality of the (3',5')-heteroconjugated oligonucleotide 18 is verified by its circularization to the DNA oligonucleotide 19 under "click" chemistry conditions.</AbstractText></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, 8800 Rockville Pike, Bethesda, Maryland 20892, USA.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Cieślak</LastName><ForeName>Jacek</ForeName><Initials>J</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>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>Beaucage</LastName><ForeName>Serge L</ForeName><Initials>SL</Initials></Author></AuthorList><Language>eng</Language><PublicationTypeList><PublicationType UI="D016428">Journal Article</PublicationType></PublicationTypeList><ArticleDate DateType="Electronic"><Year>2008</Year><Month>07</Month><Day>23</Day></ArticleDate></Article><MedlineJournalInfo><Country>United States</Country><MedlineTA>Bioconjug Chem</MedlineTA><NlmUniqueID>9010319</NlmUniqueID><ISSNLinking>1043-1802</ISSNLinking></MedlineJournalInfo><ChemicalList><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance UI="D000577">Amides</NameOfSubstance></Chemical><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance UI="D015226">Dinucleoside Phosphates</NameOfSubstance></Chemical><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance UI="D009841">Oligonucleotides</NameOfSubstance></Chemical><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance UI="D010710">Phosphates</NameOfSubstance></Chemical><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance UI="D063088">Phosphoramides</NameOfSubstance></Chemical><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance UI="D010756">Phosphoric Acids</NameOfSubstance></Chemical><Chemical><RegistryNumber>13597-72-3</RegistryNumber><NameOfSubstance UI="C005438">phosphoramide</NameOfSubstance></Chemical><Chemical><RegistryNumber>9007-49-2</RegistryNumber><NameOfSubstance UI="D004247">DNA</NameOfSubstance></Chemical><Chemical><RegistryNumber>TYM4M7EWCW</RegistryNumber><NameOfSubstance UI="C035638">thiophosphoric acid</NameOfSubstance></Chemical></ChemicalList><CitationSubset>IM</CitationSubset><MeshHeadingList><MeshHeading><DescriptorName UI="D000577" MajorTopicYN="N">Amides</DescriptorName><QualifierName UI="Q000737" MajorTopicYN="N">chemistry</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D001483" MajorTopicYN="N">Base Sequence</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D004247" MajorTopicYN="N">DNA</DescriptorName><QualifierName UI="Q000737" MajorTopicYN="Y">chemistry</QualifierName><QualifierName UI="Q000235" MajorTopicYN="N">genetics</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D015226" MajorTopicYN="N">Dinucleoside Phosphates</DescriptorName><QualifierName UI="Q000737" MajorTopicYN="N">chemistry</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D005898" MajorTopicYN="N">Glass</DescriptorName><QualifierName UI="Q000737" MajorTopicYN="Y">chemistry</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D006358" MajorTopicYN="Y">Hot Temperature</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D006863" MajorTopicYN="N">Hydrogen-Ion Concentration</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D009841" MajorTopicYN="N">Oligonucleotides</DescriptorName><QualifierName UI="Q000737" MajorTopicYN="Y">chemistry</QualifierName><QualifierName UI="Q000235" MajorTopicYN="N">genetics</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D010710" MajorTopicYN="N">Phosphates</DescriptorName><QualifierName UI="Q000737" MajorTopicYN="N">chemistry</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D063088" MajorTopicYN="N">Phosphoramides</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D010756" MajorTopicYN="N">Phosphoric Acids</DescriptorName><QualifierName UI="Q000737" MajorTopicYN="N">chemistry</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D016062" MajorTopicYN="N">Porosity</DescriptorName></MeshHeading></MeshHeadingList></MedlineCitation><PubmedData><History><PubMedPubDate PubStatus="pubmed"><Year>2008</Year><Month>7</Month><Day>24</Day><Hour>9</Hour><Minute>0</Minute></PubMedPubDate><PubMedPubDate PubStatus="medline"><Year>2008</Year><Month>10</Month><Day>22</Day><Hour>9</Hour><Minute>0</Minute></PubMedPubDate><PubMedPubDate PubStatus="entrez"><Year>2008</Year><Month>7</Month><Day>24</Day><Hour>9</Hour><Minute>0</Minute></PubMedPubDate></History><PublicationStatus>ppublish</PublicationStatus><ArticleIdList><ArticleId IdType="pubmed">18646834</ArticleId><ArticleId IdType="doi">10.1021/bc800189e</ArticleId></ArticleIdList></PubmedData></pubmed><affiliations><list><country><li>États-Unis</li></country></list><tree><noCountry><name sortKey="Beaucage, Serge L" sort="Beaucage, Serge L" uniqKey="Beaucage S" first="Serge L" last="Beaucage">Serge L. Beaucage</name><name sortKey="Cie Lak, Jacek" sort="Cie Lak, Jacek" uniqKey="Cie Lak J" first="Jacek" last="Cie Lak">Jacek Cie Lak</name><name sortKey="Duff, Robert J" sort="Duff, Robert J" uniqKey="Duff R" first="Robert J" last="Duff">Robert J. Duff</name><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><name sortKey="Kauffman, Jon S" sort="Kauffman, Jon S" uniqKey="Kauffman J" first="Jon S" last="Kauffman">Jon S. Kauffman</name><name sortKey="Norris, Scott" sort="Norris, Scott" uniqKey="Norris S" first="Scott" last="Norris">Scott Norris</name></noCountry><country name="États-Unis"><noRegion><name sortKey="Grajkowski, Andrzej" sort="Grajkowski, Andrzej" uniqKey="Grajkowski A" first="Andrzej" last="Grajkowski">Andrzej Grajkowski</name></noRegion></country></tree></affiliations></record>Pour manipuler ce document sous Unix (Dilib)
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