Direct and Facile Syntheses of Heterocyclic Vinyl-C-Nucleosides for Recognition of Inverted Base Pairs by DNA Triple Helix Formation: First Report by Direct Wittig Route

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The ability to recognize specific gene sequences canonically would allow precise means for genetic intervention. However, specific recognition of two of the four possible base pairs by triplex-forming oligonucleotides (TFO) as X.T-A and Y.C-G within a triplex currently remains elusive. A series of C1-vinyl nucleosides have been proposed, and their stability and specificity have been evaluated extensively by molecular dynamics simulation. Because most C-nucleoside syntheses extend through direct substitution at the C1-position, a more convenient strategy for their syntheses via a direct Wittig coupling is presented here.