Syntheses of silatranyl- and germatranyluridines.
[reaction: see text] Silatranyluridine 1 and germatranyluridine 2 have been prepared in five steps from oxazolinouridine 3 in 27 and 29% yields, respectively. These compounds are novel transition-state analogues (TSAs) for RNA hydrolysis and offer a number of advantages over traditional vanadium- or rhenium-based TSAs. Germatrane 2 is completely stable in D(2)O at room temperature, and the half-life of silatrane 1 in D(2)O was found to be >7 days by (1)H NMR spectroscopy.
Rink
Chad M
CM
Department of Chemistry, Xavier University, 3800 Victory Parkway, Cincinnati, Ohio 45207, USA.
Mauck
Matthew C
MC
Asif
Irfan
I
Pitzer
Michael E
ME
Fenlon
Edward E
EE
D017666:Deuterium Oxide / Q000737:chemistry; D005857:Germanium / Q000737:chemistry*; D006207:Half-Life; D006868:Hydrolysis; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D017646:Organosilicon Compounds / Q000032:analysis / Q000138:chemical synthesis*; D012313:RNA / Q000737:chemistry; D014529:Uridine / Q000031:analogs & derivatives* / Q000032:analysis / Q000138:chemical synthesis*
D017646:Organosilicon Compounds; D005857:Germanium; D012313:RNA; D017666:Deuterium Oxide; D014529:Uridine