Circular DNA by ``Bis-Click'' Ligation: Template-Independent Intramolecular Circularization of Oligonucleotides with Terminal Alkynyl Groups Utilizing Bifunctional Azides
DC Element | Wert | Sprache |
---|---|---|
dc.contributor.author | Yang, Haozhe | |
dc.contributor.author | Seela, Frank | |
dc.date.accessioned | 2021-12-23T16:06:36Z | - |
dc.date.available | 2021-12-23T16:06:36Z | - |
dc.date.issued | 2016 | |
dc.identifier.issn | 09476539 | |
dc.identifier.uri | https://osnascholar.ub.uni-osnabrueck.de/handle/unios/7469 | - |
dc.description.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. | |
dc.description.sponsorship | ChemBiotech, Munster, Germany; China Scholarship (CSC), Beijing; We thank Dr. P. Leonard and Dr. S. Budow-Busse for their continuous support throughout the preparation of this manuscript. We also thank Dr. Hui Mei for measuring the NMR spectra and Nhat Quang Tran for oligonucleotide syntheses. We would like to thank Dr. M. Letzel, Organisch-Chemisches Institut, Universitat Munster, Germany, for the measurement of the MALDI spectra. Financial support by ChemBiotech, Munster, Germany, and a China Scholarship (CSC), Beijing are gratefully acknowledged. | |
dc.language.iso | en | |
dc.publisher | WILEY-V C H VERLAG GMBH | |
dc.relation.ispartof | CHEMISTRY-A EUROPEAN JOURNAL | |
dc.subject | azides | |
dc.subject | Chemistry | |
dc.subject | Chemistry, Multidisciplinary | |
dc.subject | circularization | |
dc.subject | click chemistry | |
dc.subject | CYCLIC OLIGONUCLEOTIDES | |
dc.subject | CYCLIZATION | |
dc.subject | CYCLOADDITION | |
dc.subject | DNA | |
dc.subject | DUMBBELL OLIGODEOXYNUCLEOTIDES | |
dc.subject | EFFICIENT | |
dc.subject | PROTECTION | |
dc.subject | RNA | |
dc.subject | SIDE-CHAINS | |
dc.subject | SOLID-PHASE SYNTHESIS | |
dc.subject | synthesis design | |
dc.title | Circular DNA by ``Bis-Click'' Ligation: Template-Independent Intramolecular Circularization of Oligonucleotides with Terminal Alkynyl Groups Utilizing Bifunctional Azides | |
dc.type | journal article | |
dc.identifier.doi | 10.1002/chem.201503615 | |
dc.identifier.isi | ISI:000368922500032 | |
dc.description.volume | 22 | |
dc.description.issue | 4 | |
dc.description.startpage | 1435 | |
dc.description.endpage | 1444 | |
dc.identifier.eissn | 15213765 | |
dc.publisher.place | POSTFACH 101161, 69451 WEINHEIM, GERMANY | |
dcterms.isPartOf.abbreviation | Chem.-Eur. J. |
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geprüft am 03.06.2024