847605-68-9Relevant academic research and scientific papers
Synthesis and incorporation of C(5′)-ethynylated uracil-derived phosphoramidites into RNA
Eppacher, Simon,Christen, Markus,Vasella, Andrea
, p. 3004 - 3020 (2007/10/03)
The D-allo- and L-talo-hept-6-ynofuranosyluracil-derived phosphoramidites 11A and 11T were prepared in 9-10% yield over eight steps from the previously described propargylic alcohols 1A and 1T, respectively. The corresponding nucleotides were incorporated into rU14 by standard solid-phase synthesis. While the duplex consisting of rU14 with one L-talo-hept-6-ynofuranosyluracil in the middle of the strand and rA14 (I-V) had the same melting point as the reference duplex rU14- rA14 (I-II), the duplex with one D-allo-hept-6-ynofurano-syluracil in the middle of rU14 and rA14 (I-III) melted 1.5° lower than the reference duplex. The duplex I-VI consisting of rU14 with six L-talo-hept-6-ynofuranosyluracils distributed over the entire strand and rA14 showed a melting point that is 11° lower than the reference duplex. The corresponding duplex I-IV of rU14 possessing six D-allo-hept-6-ynofuranosyluracils and rA14 showed a melting point which is more than 20° below the one of the reference duplex. These results are in qualitative agreement with the predictions based on the conformational analysis of the nucleosides and the interference of the ethynyl moiety with the hydration of the oligonucleotides.
