208597-31-3Relevant academic research and scientific papers
Borane-amine complexes - Versatile reagents in the chemistry of nucleic acids and their analogs
Sergueeva,Sergueev,Shaw
, p. 941 - 945 (2001)
A new method for synthesis of N-alkylated nucleosides was developed. Exceptionally mild and selective conversion of N-acyl to the corresponding N-alkyl nucleosides was achieved by reduction with borane-amine complexes. The borane-amine complexes were also
Synthesis of biologically active n2-amine adducts of 2'-deoxyguanosine
Bonala,Shishkina,Johnson
, p. 7281 - 7284 (2007/10/03)
Several biologically important N2-adducts of 2'-deoxyguanosine (dG) that previously were difficultly accessible, have been synthesized directly by means of the Buchwald-Hartwig reaction. The reaction employed in each case involves the coupling
Effect of ionic state of 2'-deoxyguanosine and solvent on its aralkylation by benzyl bromide
Moon, Ki-Young,Moschel, Robert C.
, p. 696 - 702 (2007/10/03)
To extend studies of the aralkylation of nucleic acid components under a variety of solvent conditions, we determined product distributions from the reactions of benzyl bromide with 2'-deoxyguanosine and the anion of 2'- deoxyguanosine in 2,2,2-trifluoroethanol (TFE) and compared these distributions with those from the reaction of the anion with benzyl bromide in N,N-dimethylacetamide (DMA). 7-Benzylguanine was the only benzylated product detected in the reaction with the neutral nucleoside in TFE. In striking contrast, the reaction of the anion of 2'-deoxyguanosine with benzyl bromide in TFE produced N2-benzyl-2'-deoxyguanosine in significant yield and with high selectivity. The reaction of the anion of 2'-deoxyguanosine with benzyl bromide in DMA produced products derived only from reaction at the 1- and/or 7-position of the nucleoside. The weakly nucleophilic but protic polar solvent TFE and the iminolate tautomeric form of the 2'-deoxyguanosine anion appear to be essential for benzylation at the exocyclic N2-position.
