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
Journal: JOURNAL OF ORGANIC CHEMISTRY
Volumen: 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

Show full item record

Page view(s)

2
Last Week
0
Last month
0
checked on Feb 22, 2024

Google ScholarTM

Check

Altmetric