5-Bromouridine

C9HnBrN206 C2H6OS 5-Bromouridine - dimethyl sulfoxide complex BURDMS 31 369... 

CjoHi3N804 C9HuBrN206 H20 Adenosine - 5-bromouridine, monohydrate ADBURM 31 370... 

Triethylammonium uridine 3, 5 -cyclic phosphate153 5-Bromo-2 -deoxyuridine154 D-Arabinofuranosyl-5-bromouracil155 5-Bromouridine154 5-Bromouridine-methyl sulfoxide complex156... 

Deoxyadenosine monohydrate171 Adenosine-5-bromouridine monohydrate174 5-B romo-2 -deoxycytidine-2 -deoxyguanosine complex175 Thymidine176... 

Fidelity in Codon-Anticodon Interaction. Nature. 1976, 263, 289-293. Opposing view Orozco, M., Hernandez, B., Luque, F. J. Tautomerization of 1-Methyl Derivatives of Uracil, Thymine, and 5-Bromouracil. Is Tautomerization the Basis for the Mutagenicity of 5-Bromouridine J. Phys. Chem. B. 1998,102, 5228-5233.)... 

Heavy atom incorporation for phasing can also be accomplished through the use of modified nucleosides. Specifically, 5-bromouridine (Adams et al, 2004 Baugh etal, 2000 Kieft etal, 2002 Martickand Scott, 2006), 5-iodour-idine (Klein et al, 2009), STa-P-seleno-triphosphates (Brandt et al, 2006),... 

ADBURM. Adenosine-5-bromouridine monohydrate C10H13N3O4 C9H11BrN206, HzO. 

Generation of site-specifically modified RNAs that can perform disulfide cross-linking allows for RNA folding pathways to be examined (21, 54). Photoactivated cross-linking is another strategy that uses naturally occurring or synthetic modifications, such as 4-thiouridine, 6-thioguanosine, 5-bromouridine, and 5-iodouridine (Table 1), to study RNA-RNA interactions in folded RNAs (19). 

Replacement of all uridine residues in the Tetrahymena group I ribozyme with 5-bromouridine results in a 13-fold reduction in catalytic efficiency. " Using a library of 10 ribozymes with 5-bromouridine instead of uridine gave after 5 rounds of selection a 27-fold increase in catalytic efficiency compared to the uridine ribozyme. 

Sierakowska, H., Shukla, R.R., Dominski, Z., and Kole, R. (1989). Inhibition of pre-mRNA splicing by 5-fluoro-, 5-chloro-, and 5-bromouridine. J. Biol. Chem. 264 19185-19191. 

As pyrimidine nucleosides are rather stable under acidic conditions, they may be phosphorylated with a mixture of 85% phosphoric acid and phosphorus pentaoxide ( polyphosphoric acid )- The 2, 3 -0-isopropylidene acetals of uridine and of cytidine were treated with polyphosphoric acid for two hours at 60°. After acid hydrolysis, the 5 -phosphates of these nucleosides were obtained in good yield. 2, 3 -0-Benzylidenecytidine was phosphorylated similarly to cytidine 5 -phosphate. The polyphosphoric acid method was also used to convert the 2, 3 -0-isopropylidene acetals of 5-bromouridine, 3-methyluridine, and A -methyl- and A -dimethyl-cytidine into their respective nucleoside 5 -phosphates. 

The reaction of cyanide with a protected 5-bromouridine is instructive under mild conditions a cine-substituted product is obtained via a Michael addition followed by p-elimination of bromide, but at higher temperatures, conversion of the 6- into the 5-cyano-isomer is observed, i.e. the product of apparent, direct displacement of bromide is obtained. The higher-temperature product arises via an isomerisation involving another Michael addition, then elimination of the 6-cyano group. 

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