title: 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.
abstract: 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.
authors: Division of Experimental Therapeutics, Department of Medicine, Columbia University Medical Center, 630 West 168th Street, New York, New York 10032, USA. jhr21@columbia.edu
authors: Jeffrey H
authors: JH
authors: Rothman
mesh_terms: D020029:Base Pairing; D004247:DNA / Q000737:chemistry*; D006571:Heterocyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D009705:Nucleosides / Q000138:chemical synthesis / Q000737:chemistry*; D014753:Vinyl Compounds / Q000737:chemistry*
chemical_list: D006571:Heterocyclic Compounds; D009705:Nucleosides; D014753:Vinyl Compounds; D004247:DNA