Synthesis and incorporation of a furan-modified adenosine building block for DNA interstrand crosslinking

2'-O-(3-(Furan-2-yl)propyl)adenosine was synthesized and evaluated for interstrand crosslink (ICL) formation in DNA duplexes. In situ oxidation of the furan moiety with NIS showed rapid crosslink formation to dA and dC, while dT and dG were inactive.

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Bibliographische Detailangaben
Veröffentlicht in:	Chemical communications (Cambridge, England) England), 2011-01, Vol.47 (10), p.2796-2798
Hauptverfasser:	Jawalekar, Anup M, Op de Beeck, Marieke, van Delft, Floris L, Madder, Annemieke
Format:	Artikel
Sprache:	eng
Schlagworte:	Adenosine Adenosine - analogs & derivatives Adenosine - chemical synthesis Adenosine - chemistry Base Sequence Bromosuccinimide - chemistry Chemical communication Cross-Linking Reagents - chemical synthesis Cross-Linking Reagents - chemistry DNA DNA - chemistry DNA - genetics Furans Furans - chemical synthesis Furans - chemistry Oxidation Oxidation-Reduction Succinimides - chemistry
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Beschreibung
Zusammenfassung:	2'-O-(3-(Furan-2-yl)propyl)adenosine was synthesized and evaluated for interstrand crosslink (ICL) formation in DNA duplexes. In situ oxidation of the furan moiety with NIS showed rapid crosslink formation to dA and dC, while dT and dG were inactive.
ISSN:	1359-7345 1364-548X
DOI:	10.1039/c0cc04667a