Cross-Linked DNA Generated by ``Bis-click'' Reactions with Bis-functional Azides: Site Independent Ligation of Oligonucleotides via Nucleobase Alkynyl Chains
Autor(en): | Pujari, Suresh S. Xiong, Hai Seela, Frank |
Stichwörter: | Chemistry; Chemistry, Organic; CIRCULARIZATION; CYCLOADDITION; DUPLEXES; FOLDING DNA; LINKING; NANOSCALE SHAPES; SIDE-CHAINS; SOLID SUPPORT; TERMINAL ALKYNES | Erscheinungsdatum: | 2010 | Herausgeber: | AMER CHEMICAL SOC | Enthalten in: | JOURNAL OF ORGANIC CHEMISTRY | Band: | 75 | Ausgabe: | 24 | Startseite: | 8693 | Seitenende: | 8696 | Zusammenfassung: | Template-free cross-linking of single-stranded DNA bearing octadiynyl side chains at the 7-position of 8-aza-7-deazapurine moieties with bisfunctional azides is reported employing a Cu(I)-catalyzed azide alkyne ``bis-click'' reaction. Bis-adducts were formed when the bis-azide:oligonucleotide ratio was 1:1; monofunctionalization occurred when the ratio was 15:1. Four-stranded DNA consisting of two cross-linked duplexes was obtained after hydridization. Cross-linked duplexes are as stable as individual duplexes when ligation was introduced at terminal positions; ligation at a central position led to a slight duplex destabilization. |
ISSN: | 00223263 | DOI: | 10.1021/jo101809w |
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geprüft am 07.06.2024