849354-91-2

Upstream product

• 849354-89-8 2'-deoxy-2'-(2-furyl-2-ethoxycarbonylamino)uridine 
• 40615-36-9 4,4'-dimethoxytrityl chloride 
• 539-47-9 3-(fur-2-yl)crotonic acid 
• 3736-77-4 2,2'-Anhydrouridine 
• 58-96-8 uridine 
• 539-47-9 3-(2-furyl)acrylic acid 
• 26929-65-7 2'-azido-2'-deoxyuridine 
• 935-13-7 3-(2-furyl)propanoic acid 
• 849354-88-7 pentafluorophenyl-3-(2-furyl)-propanoate 

Relevant academic research and scientific papers

Unprecedented C-selective interstrand cross-linking through in situ oxidation of furan-modified oligodeoxynucleotides

Chemical reagents that form interstrand cross-links have been used for a long time in cancer therapy. They covalently link two strands of DNA, thereby blocking transcription. Cross-link repair enzymes, however, can restore the transcription processes, causing resistance to certain anti-cancer drugs. The mechanism of these cross-link repair processes has not yet been fully revealed. One of the obstacles in this study is the lack of sufficient amounts of well-defined, stable, cross-linked duplexes to study the pathways of cross-link repair enzymes. Our group has developed a cross-link strategy where a furan moiety is incorporated into oligodeoxynucleotides (ODNs). These furan-modified nucleic acids can form interstrand crosslinks upon selective furan oxidation with N-bromosuccinimide.We here report on the incorporation of the furan moiety at the 20-position of a uridine through an amido or ureido linker. The resulting modified ODNs display an unprecedented selectivity for cross-linking toward a cytidine opposite the modified residue, forming one specific cross-linked duplex, which could be isolated in good yield. Furthermore, the structure of the formed cross-linked duplexes could be unambiguously characterized.

Fine-tuning furan toxicity: Fast and quantitative DNA interchain cross-link formation upon selective oxidation of a furan containing oligonucleotide

Oligonucleotides containing a furan modified internal nucleoside have been synthesized; selective in situ oxidation of the furan moiety to a reactive enal species in the presence of a complementary DNA strand gives rise to fast and efficient formation of an interstrand cross-link. The Royal Society of Chemistry 2005.