6-azapyrimidine and 7-deazapurine 2'-deoxy-2'-fluoroarabinonucleosides: synthesis, conformation and properties of oligonucleotides.
The synthesis of 2'-deoxy-2'-fluoro-beta-D-arabinofuranosyl nucleosides (1b, 2b, and 3b) were described and their conformation in solution as well as in the solid state was determined In addition to this, building blocks 10a,b and 13a,b were prepared and employed in solid-phase oligonucleotide synthesis. For compounds 1a and 1b the lactime proton is protected to avoid unresolved degradation of its phosphoramidites 10a,b. UV-melting studies have been carried out to assess the thermal stability of oligonucleotides containing compounds 1a,b, and 3a,b.
Seela
Frank
F
Laboratorium für Organische und Bioorganische Chemie, Institut für Chemie, Universität, Osnabrück, Germany.
Chittepu
Padmaja
P
He
Yang
Y
He
Junlin
J
Xu
Kuiying
K
D001087:Arabinonucleosides / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D002626:Chemistry, Pharmaceutical / Q000379:methods; D015195:Drug Design; D008956:Models, Chemical; D008968:Molecular Conformation; D009584:Nitrogen / Q000737:chemistry; D009705:Nucleosides / Q000737:chemistry; D009841:Oligonucleotides / Q000737:chemistry; D011522:Protons; D011684:Purine Nucleosides / Q000138:chemical synthesis* / Q000737:chemistry; D011741:Pyrimidine Nucleosides / Q000138:chemical synthesis* / Q000737:chemistry; D013696:Temperature; D013816:Thermodynamics; D014466:Ultraviolet Rays
D001087:Arabinonucleosides; D009705:Nucleosides; D009841:Oligonucleotides; D011522:Protons; D011684:Purine Nucleosides; D011741:Pyrimidine Nucleosides; D009584:Nitrogen