``Bis-Click'' Ligation of DNA: Template-Controlled Assembly, Circularisation and Functionalisation with Bifunctional and Trifunctional Azides

Autor(en): Yang, Haozhe
Seela, Frank
Stichwörter: ALKYNE CYCLOADDITION; Chemistry; Chemistry, Multidisciplinary; CIRCULARIZATION; CYCLIZATION; OLIGONUCLEOTIDES; PHASE; SIDE-CHAINS; STABILITY; STRATEGIES; TERMINAL ALKYNES
Erscheinungsdatum: 2017
Herausgeber: WILEY-V C H VERLAG GMBH
Journal: CHEMISTRY-A EUROPEAN JOURNAL
Volumen: 23
Ausgabe: 14
Startseite: 3375
Seitenende: 3385
Zusammenfassung: 
Ligation and circularisation of oligonucleotides containing terminal triple bonds was performed with bifunctional or trifunctional azides. Both reactions are high yielding. Template-assisted bis-click ligation of two individual non-complementary oligonucleotide strands was accomplished to yield heterodimers exclusively. In this context, the template fulfils two functions: it accelerates the ligation reaction and controls product assembly (heterodimer vs. homodimer formation). Intermolecular bis-click circularisation of one oligonucleotide strand took place without template assistance. For construction of oligonucleotides with terminal triple bonds in the nucleobase side chain, 7- or 5functionalised 7-deaza-dA and dU residues were used. These oligonucleotides are directly accessible by solid-phase synthesis. When trifunctional azides were employed instead of bifunctional linkers, functionalisation of the remaining azido group was performed with small molecules such as 1-ethynyl pyrene, biotin propargyl amide or with ethynylated
ISSN: 09476539
DOI: 10.1002/chem.201604857

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