Syntheses of Silatranyl- and Germatranyluridines

Syntheses of Silatranyl- and Germatranyluridines

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....

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Veröffentlicht in:Organic letters 2005-03, Vol.7 (6), p.1165-1168
Hauptverfasser: Rink, Chad M, Mauck, Matthew C, Asif, Irfan, Pitzer, Michael E, Fenlon, Edward E
Format: Artikel
Sprache:eng
Schlagworte:
Deuterium Oxide - chemistry
Germanium - chemistry
Half-Life
Hydrolysis
Magnetic Resonance Spectroscopy
Molecular Structure
Organosilicon Compounds - analysis
Organosilicon Compounds - chemical synthesis
RNA - chemistry
Uridine - analogs & derivatives
Uridine - analysis
Uridine - chemical synthesis
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Beschreibung
Zusammenfassung: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 D2O at room temperature, and the half-life of silatrane 1 in D2O was found to be >7 days by 1H NMR spectroscopy.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol050133v