Circular DNA by "Bis-Click" Ligation: Template-Independent Intramolecular Circularization of Oligonucleotides with Terminal Alkynyl Groups Utilizing Bifunctional Azides.
Identifieur interne : 001340 ( PubMed/Curation ); précédent : 001339; suivant : 001341Circular DNA by "Bis-Click" Ligation: Template-Independent Intramolecular Circularization of Oligonucleotides with Terminal Alkynyl Groups Utilizing Bifunctional Azides.
Auteurs : Haozhe Yang [Allemagne] ; Frank Seela [Allemagne]Source :
- Chemistry (Weinheim an der Bergstrasse, Germany) [ 1521-3765 ] ; 2016.
Descripteurs français
- KwdFr :
- ADN (), ADN circulaire (), ADN circulaire (synthèse chimique), Alcynes (), Appariement de bases, Azotures (), Chimie click, Colorants fluorescents (), Cuivre (), Dérivés du benzène (), Désoxyadénosine (), Ligature, Oligonucléotides (), Oligonucléotides (synthèse chimique), Polyosides (), Réaction de cycloaddition, Techniques de synthèse en phase solide, Tubercidine (), Tubercidine (analogues et dérivés).
- MESH :
- analogues et dérivés : Tubercidine.
- synthèse chimique : ADN circulaire, Oligonucléotides.
- ADN, ADN circulaire, Alcynes, Appariement de bases, Azotures, Chimie click, Colorants fluorescents, Cuivre, Dérivés du benzène, Désoxyadénosine, Ligature, Oligonucléotides, Polyosides, Réaction de cycloaddition, Techniques de synthèse en phase solide, Tubercidine.
English descriptors
- KwdEn :
- Alkynes (chemistry), Azides (chemistry), Base Pairing, Benzene Derivatives (chemistry), Click Chemistry, Copper (chemistry), Cycloaddition Reaction, DNA (chemistry), DNA, Circular (chemical synthesis), DNA, Circular (chemistry), Deoxyadenosines (chemistry), Fluorescent Dyes (chemistry), Ligation, Oligonucleotides (chemical synthesis), Oligonucleotides (chemistry), Polysaccharides (chemistry), Solid-Phase Synthesis Techniques, Tubercidin (analogs & derivatives), Tubercidin (chemistry).
- MESH :
- chemical , analogs & derivatives : Tubercidin.
- chemical , chemical synthesis : DNA, Circular, Oligonucleotides.
- chemical , chemistry : Alkynes, Azides, Benzene Derivatives, Copper, DNA, DNA, Circular, Deoxyadenosines, Fluorescent Dyes, Oligonucleotides, Polysaccharides, Tubercidin.
- Base Pairing, Click Chemistry, Cycloaddition Reaction, Ligation, Solid-Phase Synthesis Techniques.
Abstract
A highly effective and convenient "bis-click" strategy was developed for the template-independent circularization of single-stranded oligonucleotides by employing copper(I)-assisted azide-alkyne cycloaddition. Terminal triple bonds were incorporated at both ends of linear oligonucleotides. Alkynylated 7-deaza-2'-deoxyadenosine and 2'-deoxyuridine residues with different side chains were used in solid-phase synthesis with phosphoramidite chemistry. The bis-click ligation of linear 9- to 36-mer oligonucleotides with 1,4-bis(azidomethyl)benzene afforded circular DNA in a simple and selective way; azido modification of the oligonucleotide was not necessary. Short ethynyl side chains were compatible with the circularization of longer oligonucleotides, whereas octadiynyl residues were used for short 9-mers. Compared with linear duplexes, circular bis-click constructs exhibit a significantly increased duplex stability over their linear counterparts. The intramolecular bis-click ligation protocol is not limited to DNA, but may also be suitable for the construction of other macrocycles, such as circular RNAs, peptides, or polysaccharides.
DOI: 10.1002/chem.201503615
PubMed: 26685101
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Center for Nanotechnology, Heisenbergstrasse 11, 48149, Münster, Germany. frank.seela@uni-osnabrueck.de.</nlm:affiliation><country xml:lang="fr">Allemagne</country><wicri:regionArea>Laboratory of Bioorganic Chemistry and Chemical Biology, Center for Nanotechnology, Heisenbergstrasse 11, 48149, Münster</wicri:regionArea></affiliation></author></titleStmt><publicationStmt><idno type="wicri:source">PubMed</idno><date when="2016">2016</date><idno type="RBID">pubmed:26685101</idno><idno type="pmid">26685101</idno><idno type="doi">10.1002/chem.201503615</idno><idno type="wicri:Area/PubMed/Corpus">001340</idno><idno type="wicri:explorRef" wicri:stream="PubMed" wicri:step="Corpus" wicri:corpus="PubMed">001340</idno><idno type="wicri:Area/PubMed/Curation">001340</idno><idno type="wicri:explorRef" wicri:stream="PubMed" wicri:step="Curation">001340</idno></publicationStmt><sourceDesc><biblStruct><analytic><title xml:lang="en">Circular DNA by "Bis-Click" Ligation: Template-Independent Intramolecular Circularization of Oligonucleotides with Terminal Alkynyl Groups Utilizing Bifunctional Azides.</title><author><name sortKey="Yang, Haozhe" sort="Yang, Haozhe" uniqKey="Yang H" first="Haozhe" last="Yang">Haozhe Yang</name><affiliation wicri:level="1"><nlm:affiliation>Laboratory of Bioorganic Chemistry and Chemical Biology, Center for Nanotechnology, Heisenbergstrasse 11, 48149, Münster, Germany.</nlm:affiliation><country xml:lang="fr">Allemagne</country><wicri:regionArea>Laboratory of Bioorganic Chemistry and Chemical Biology, Center for Nanotechnology, Heisenbergstrasse 11, 48149, Münster</wicri:regionArea></affiliation></author><author><name sortKey="Seela, Frank" sort="Seela, Frank" uniqKey="Seela F" first="Frank" last="Seela">Frank Seela</name><affiliation wicri:level="1"><nlm:affiliation>Laboratory of Bioorganic Chemistry and Chemical Biology, Center for Nanotechnology, Heisenbergstrasse 11, 48149, Münster, Germany. frank.seela@uni-osnabrueck.de.</nlm:affiliation><country xml:lang="fr">Allemagne</country><wicri:regionArea>Laboratory of Bioorganic Chemistry and Chemical Biology, Center for Nanotechnology, Heisenbergstrasse 11, 48149, Münster</wicri:regionArea></affiliation></author></analytic><series><title level="j">Chemistry (Weinheim an der Bergstrasse, Germany)</title><idno type="eISSN">1521-3765</idno><imprint><date when="2016" type="published">2016</date></imprint></series></biblStruct></sourceDesc></fileDesc><profileDesc><textClass><keywords scheme="KwdEn" xml:lang="en"><term>Alkynes (chemistry)</term><term>Azides (chemistry)</term><term>Base Pairing</term><term>Benzene Derivatives (chemistry)</term><term>Click Chemistry</term><term>Copper (chemistry)</term><term>Cycloaddition Reaction</term><term>DNA (chemistry)</term><term>DNA, Circular (chemical synthesis)</term><term>DNA, Circular (chemistry)</term><term>Deoxyadenosines (chemistry)</term><term>Fluorescent Dyes (chemistry)</term><term>Ligation</term><term>Oligonucleotides (chemical synthesis)</term><term>Oligonucleotides (chemistry)</term><term>Polysaccharides (chemistry)</term><term>Solid-Phase Synthesis Techniques</term><term>Tubercidin (analogs & derivatives)</term><term>Tubercidin (chemistry)</term></keywords><keywords scheme="KwdFr" xml:lang="fr"><term>ADN ()</term><term>ADN circulaire ()</term><term>ADN circulaire (synthèse chimique)</term><term>Alcynes ()</term><term>Appariement de bases</term><term>Azotures ()</term><term>Chimie click</term><term>Colorants fluorescents ()</term><term>Cuivre ()</term><term>Dérivés du benzène ()</term><term>Désoxyadénosine ()</term><term>Ligature</term><term>Oligonucléotides ()</term><term>Oligonucléotides (synthèse chimique)</term><term>Polyosides ()</term><term>Réaction de cycloaddition</term><term>Techniques de synthèse en phase solide</term><term>Tubercidine ()</term><term>Tubercidine (analogues et dérivés)</term></keywords><keywords scheme="MESH" type="chemical" qualifier="analogs & derivatives" xml:lang="en"><term>Tubercidin</term></keywords><keywords scheme="MESH" type="chemical" qualifier="chemical synthesis" xml:lang="en"><term>DNA, Circular</term><term>Oligonucleotides</term></keywords><keywords scheme="MESH" type="chemical" qualifier="chemistry" xml:lang="en"><term>Alkynes</term><term>Azides</term><term>Benzene Derivatives</term><term>Copper</term><term>DNA</term><term>DNA, Circular</term><term>Deoxyadenosines</term><term>Fluorescent Dyes</term><term>Oligonucleotides</term><term>Polysaccharides</term><term>Tubercidin</term></keywords><keywords scheme="MESH" qualifier="analogues et dérivés" xml:lang="fr"><term>Tubercidine</term></keywords><keywords scheme="MESH" qualifier="synthèse chimique" xml:lang="fr"><term>ADN circulaire</term><term>Oligonucléotides</term></keywords><keywords scheme="MESH" xml:lang="en"><term>Base Pairing</term><term>Click Chemistry</term><term>Cycloaddition Reaction</term><term>Ligation</term><term>Solid-Phase Synthesis Techniques</term></keywords><keywords scheme="MESH" xml:lang="fr"><term>ADN</term><term>ADN circulaire</term><term>Alcynes</term><term>Appariement de bases</term><term>Azotures</term><term>Chimie click</term><term>Colorants fluorescents</term><term>Cuivre</term><term>Dérivés du benzène</term><term>Désoxyadénosine</term><term>Ligature</term><term>Oligonucléotides</term><term>Polyosides</term><term>Réaction de cycloaddition</term><term>Techniques de synthèse en phase solide</term><term>Tubercidine</term></keywords></textClass></profileDesc></teiHeader><front><div type="abstract" xml:lang="en">A highly effective and convenient "bis-click" strategy was developed for the template-independent circularization of single-stranded oligonucleotides by employing copper(I)-assisted azide-alkyne cycloaddition. Terminal triple bonds were incorporated at both ends of linear oligonucleotides. Alkynylated 7-deaza-2'-deoxyadenosine and 2'-deoxyuridine residues with different side chains were used in solid-phase synthesis with phosphoramidite chemistry. The bis-click ligation of linear 9- to 36-mer oligonucleotides with 1,4-bis(azidomethyl)benzene afforded circular DNA in a simple and selective way; azido modification of the oligonucleotide was not necessary. Short ethynyl side chains were compatible with the circularization of longer oligonucleotides, whereas octadiynyl residues were used for short 9-mers. Compared with linear duplexes, circular bis-click constructs exhibit a significantly increased duplex stability over their linear counterparts. The intramolecular bis-click ligation protocol is not limited to DNA, but may also be suitable for the construction of other macrocycles, such as circular RNAs, peptides, or polysaccharides. </div></front></TEI><pubmed><MedlineCitation Status="MEDLINE" Owner="NLM"><PMID Version="1">26685101</PMID><DateCompleted><Year>2016</Year><Month>06</Month><Day>28</Day></DateCompleted><DateRevised><Year>2016</Year><Month>01</Month><Day>14</Day></DateRevised><Article PubModel="Print-Electronic"><Journal><ISSN IssnType="Electronic">1521-3765</ISSN><JournalIssue CitedMedium="Internet"><Volume>22</Volume><Issue>4</Issue><PubDate><Year>2016</Year><Month>Jan</Month><Day>22</Day></PubDate></JournalIssue><Title>Chemistry (Weinheim an der Bergstrasse, Germany)</Title><ISOAbbreviation>Chemistry</ISOAbbreviation></Journal><ArticleTitle>Circular DNA by "Bis-Click" Ligation: Template-Independent Intramolecular Circularization of Oligonucleotides with Terminal Alkynyl Groups Utilizing Bifunctional Azides.</ArticleTitle><Pagination><MedlinePgn>1435-44</MedlinePgn></Pagination><ELocationID EIdType="doi" ValidYN="Y">10.1002/chem.201503615</ELocationID><Abstract><AbstractText>A highly effective and convenient "bis-click" strategy was developed for the template-independent circularization of single-stranded oligonucleotides by employing copper(I)-assisted azide-alkyne cycloaddition. Terminal triple bonds were incorporated at both ends of linear oligonucleotides. Alkynylated 7-deaza-2'-deoxyadenosine and 2'-deoxyuridine residues with different side chains were used in solid-phase synthesis with phosphoramidite chemistry. The bis-click ligation of linear 9- to 36-mer oligonucleotides with 1,4-bis(azidomethyl)benzene afforded circular DNA in a simple and selective way; azido modification of the oligonucleotide was not necessary. Short ethynyl side chains were compatible with the circularization of longer oligonucleotides, whereas octadiynyl residues were used for short 9-mers. Compared with linear duplexes, circular bis-click constructs exhibit a significantly increased duplex stability over their linear counterparts. The intramolecular bis-click ligation protocol is not limited to DNA, but may also be suitable for the construction of other macrocycles, such as circular RNAs, peptides, or polysaccharides. </AbstractText><CopyrightInformation>© 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.</CopyrightInformation></Abstract><AuthorList CompleteYN="Y"><Author ValidYN="Y"><LastName>Yang</LastName><ForeName>Haozhe</ForeName><Initials>H</Initials><AffiliationInfo><Affiliation>Laboratory of Bioorganic Chemistry and Chemical Biology, Center for Nanotechnology, Heisenbergstrasse 11, 48149, Münster, Germany.</Affiliation></AffiliationInfo><AffiliationInfo><Affiliation>Laboratorium für Organische und Bioorganische Chemie, Institut für Chemie neuer Materialien, Universität Osnabrück, Barbarastrasse 7, 49069, Osnabrück, Germany), Fax: (+49) 251-53406857.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Seela</LastName><ForeName>Frank</ForeName><Initials>F</Initials><AffiliationInfo><Affiliation>Laboratory of Bioorganic Chemistry and Chemical Biology, Center for Nanotechnology, Heisenbergstrasse 11, 48149, Münster, Germany. frank.seela@uni-osnabrueck.de.</Affiliation></AffiliationInfo><AffiliationInfo><Affiliation>Laboratorium für Organische und Bioorganische Chemie, Institut für Chemie neuer Materialien, Universität Osnabrück, Barbarastrasse 7, 49069, Osnabrück, Germany), Fax: (+49) 251-53406857. frank.seela@uni-osnabrueck.de.</Affiliation></AffiliationInfo></Author></AuthorList><Language>eng</Language><PublicationTypeList><PublicationType UI="D016428">Journal Article</PublicationType><PublicationType UI="D013485">Research Support, Non-U.S. Gov't</PublicationType></PublicationTypeList><ArticleDate DateType="Electronic"><Year>2015</Year><Month>12</Month><Day>18</Day></ArticleDate></Article><MedlineJournalInfo><Country>Germany</Country><MedlineTA>Chemistry</MedlineTA><NlmUniqueID>9513783</NlmUniqueID><ISSNLinking>0947-6539</ISSNLinking></MedlineJournalInfo><ChemicalList><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance UI="C000608606">1,4-bis(azidomethyl)benzene</NameOfSubstance></Chemical><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance UI="D000480">Alkynes</NameOfSubstance></Chemical><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance UI="D001386">Azides</NameOfSubstance></Chemical><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance UI="D001555">Benzene Derivatives</NameOfSubstance></Chemical><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance UI="D004270">DNA, Circular</NameOfSubstance></Chemical><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance UI="D003839">Deoxyadenosines</NameOfSubstance></Chemical><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance UI="D005456">Fluorescent Dyes</NameOfSubstance></Chemical><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance UI="D009841">Oligonucleotides</NameOfSubstance></Chemical><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance UI="D011134">Polysaccharides</NameOfSubstance></Chemical><Chemical><RegistryNumber>60129-59-1</RegistryNumber><NameOfSubstance UI="C053222">2'-deoxytubercidin</NameOfSubstance></Chemical><Chemical><RegistryNumber>789U1901C5</RegistryNumber><NameOfSubstance UI="D003300">Copper</NameOfSubstance></Chemical><Chemical><RegistryNumber>9007-49-2</RegistryNumber><NameOfSubstance UI="D004247">DNA</NameOfSubstance></Chemical><Chemical><RegistryNumber>M351LCX45Y</RegistryNumber><NameOfSubstance UI="D014372">Tubercidin</NameOfSubstance></Chemical></ChemicalList><CitationSubset>IM</CitationSubset><MeshHeadingList><MeshHeading><DescriptorName UI="D000480" MajorTopicYN="N">Alkynes</DescriptorName><QualifierName UI="Q000737" MajorTopicYN="Y">chemistry</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D001386" MajorTopicYN="N">Azides</DescriptorName><QualifierName UI="Q000737" MajorTopicYN="Y">chemistry</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D020029" MajorTopicYN="N">Base Pairing</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D001555" MajorTopicYN="N">Benzene Derivatives</DescriptorName><QualifierName UI="Q000737" MajorTopicYN="Y">chemistry</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D057930" MajorTopicYN="N">Click Chemistry</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D003300" MajorTopicYN="N">Copper</DescriptorName><QualifierName UI="Q000737" MajorTopicYN="N">chemistry</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D061565" MajorTopicYN="N">Cycloaddition Reaction</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D004247" MajorTopicYN="N">DNA</DescriptorName><QualifierName UI="Q000737" MajorTopicYN="Y">chemistry</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D004270" MajorTopicYN="N">DNA, Circular</DescriptorName><QualifierName UI="Q000138" MajorTopicYN="Y">chemical synthesis</QualifierName><QualifierName UI="Q000737" MajorTopicYN="Y">chemistry</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D003839" MajorTopicYN="N">Deoxyadenosines</DescriptorName><QualifierName UI="Q000737" MajorTopicYN="Y">chemistry</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D005456" MajorTopicYN="N">Fluorescent Dyes</DescriptorName><QualifierName UI="Q000737" MajorTopicYN="Y">chemistry</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D008026" MajorTopicYN="N">Ligation</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D009841" MajorTopicYN="N">Oligonucleotides</DescriptorName><QualifierName UI="Q000138" MajorTopicYN="N">chemical synthesis</QualifierName><QualifierName UI="Q000737" MajorTopicYN="Y">chemistry</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D011134" MajorTopicYN="N">Polysaccharides</DescriptorName><QualifierName UI="Q000737" MajorTopicYN="N">chemistry</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D060327" MajorTopicYN="N">Solid-Phase Synthesis Techniques</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D014372" MajorTopicYN="N">Tubercidin</DescriptorName><QualifierName UI="Q000031" MajorTopicYN="Y">analogs & derivatives</QualifierName><QualifierName UI="Q000737" MajorTopicYN="N">chemistry</QualifierName></MeshHeading></MeshHeadingList><KeywordList Owner="NOTNLM"><Keyword MajorTopicYN="N">DNA</Keyword><Keyword MajorTopicYN="N">azides</Keyword><Keyword MajorTopicYN="N">circularization</Keyword><Keyword MajorTopicYN="N">click chemistry</Keyword><Keyword MajorTopicYN="N">synthesis design</Keyword></KeywordList></MedlineCitation><PubmedData><History><PubMedPubDate PubStatus="received"><Year>2015</Year><Month>09</Month><Day>09</Day></PubMedPubDate><PubMedPubDate PubStatus="entrez"><Year>2015</Year><Month>12</Month><Day>20</Day><Hour>6</Hour><Minute>0</Minute></PubMedPubDate><PubMedPubDate PubStatus="pubmed"><Year>2015</Year><Month>12</Month><Day>20</Day><Hour>6</Hour><Minute>0</Minute></PubMedPubDate><PubMedPubDate PubStatus="medline"><Year>2016</Year><Month>6</Month><Day>29</Day><Hour>6</Hour><Minute>0</Minute></PubMedPubDate></History><PublicationStatus>ppublish</PublicationStatus><ArticleIdList><ArticleId IdType="pubmed">26685101</ArticleId><ArticleId IdType="doi">10.1002/chem.201503615</ArticleId></ArticleIdList></PubmedData></pubmed></record>Pour manipuler ce document sous Unix (Dilib)
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