Circular DNA by "Bis-Click" Ligation: Template-Independent Intramolecular Circularization of Oligonucleotides with Terminal Alkynyl Groups Utilizing Bifunctional Azides.
Identifieur interne : 001346 ( Main/Exploration ); précédent : 001345; suivant : 001347Circular 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
Affiliations:
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Le document en format XML
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Azides.</title><author><name sortKey="Yang, Haozhe" sort="Yang, Haozhe" uniqKey="Yang H" first="Haozhe" last="Yang">Haozhe Yang</name><affiliation wicri:level="3"><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><placeName><region type="land" nuts="1">Rhénanie-du-Nord-Westphalie</region><region type="district" nuts="2">District de Münster</region><settlement type="city">Münster</settlement></placeName></affiliation></author><author><name sortKey="Seela, Frank" sort="Seela, Frank" uniqKey="Seela F" first="Frank" last="Seela">Frank Seela</name><affiliation wicri:level="3"><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><placeName><region type="land" nuts="1">Rhénanie-du-Nord-Westphalie</region><region type="district" nuts="2">District de Münster</region><settlement type="city">Münster</settlement></placeName></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><affiliations><list><country><li>Allemagne</li></country><region><li>District de Münster</li><li>Rhénanie-du-Nord-Westphalie</li></region><settlement><li>Münster</li></settlement></list><tree><country name="Allemagne"><region name="Rhénanie-du-Nord-Westphalie"><name sortKey="Yang, Haozhe" sort="Yang, Haozhe" uniqKey="Yang H" first="Haozhe" last="Yang">Haozhe Yang</name></region><name sortKey="Seela, Frank" sort="Seela, Frank" uniqKey="Seela F" first="Frank" last="Seela">Frank Seela</name></country></tree></affiliations></record>Pour manipuler ce document sous Unix (Dilib)
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