SYNTHESIS AND PURIFICATION OF FLUORINATED BENZIMIDAZOLE AND BENZENE NUCLEOSIDE-5′-TRIPHOSPHATES

• Published in: Nucleosides, nucleotides & nucleic acids nucleotides & nucleic acids, 2005-01, Vol.24 (5-7), p.651-654
• Main Authors: Klöpffer, A. E., Engels, J. W.
• Format: Article
• Language: English
• Subjects: Benzene - chemistry; Benzimidazoles - chemical synthesis; Benzimidazoles - isolation & purification; Chromatography, High Pressure Liquid; Dinucleoside Phosphates - chemical synthesis; Dinucleoside Phosphates - isolation & purification; DNA-Directed RNA Polymerases - metabolism; Fluorobenzenes - chemistry; Formamides - chemistry; Magnetic Resonance Spectroscopy; Models, Chemical; Molecular Biology - instrumentation; Molecular Biology - methods; Nucleic Acid Heteroduplexes - chemistry; Nucleosides - chemistry; Nucleotides - chemistry; Phosphates - chemistry; RNA - chemistry; Spectrometry, Mass, Electrospray Ionization; Substrate Specificity; Time Factors; Viral Proteins - metabolism
• ISSN: 1525-7770; 1532-2335
• DOI: 10.1081/NCN-200060151

The expression "universal base" is very often used to express hybridization properties and recognition patterns of nucleosides. Their behaviour in biological applications, however, is of great interest regarding, e.g., their incorporation by polymerases. The 4,6-difluorobenzimidazole and the 2,4-difluorobenzene nucleoside analogues have proven to be universal bases that do not discriminate between the four natural nucleobases in RNA duplexes. Therefore, we synthesized the corresponding triphosphates to evaluate their behavior in polymerase catalyzed reactions and to investigate their ability to serve as substrates for the T7 RNA polymerase.