Circular DNA by ``Bis-Click'' Ligation: Template-Independent Intramolecular Circularization of Oligonucleotides with Terminal Alkynyl Groups Utilizing Bifunctional Azides

Autor(en): Yang, Haozhe
Seela, Frank
Stichwörter: azides; Chemistry; Chemistry, Multidisciplinary; circularization; click chemistry; CYCLIC OLIGONUCLEOTIDES; CYCLIZATION; CYCLOADDITION; DNA; DUMBBELL OLIGODEOXYNUCLEOTIDES; EFFICIENT; PROTECTION; RNA; SIDE-CHAINS; SOLID-PHASE SYNTHESIS; synthesis design
Erscheinungsdatum: 2016
Herausgeber: WILEY-V C H VERLAG GMBH
Journal: CHEMISTRY-A EUROPEAN JOURNAL
Volumen: 22
Ausgabe: 4
Startseite: 1435
Seitenende: 1444
Zusammenfassung: 
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.
ISSN: 09476539
DOI: 10.1002/chem.201503615

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