Synthesis and hybridization properties of an acyclic achiral phosphonate DNA analogue.
Protected N-(2-hydroxyethyl)-N-(nucleobase-acetyl)aminomethanephosphonic+ ++ acid (6a-d) of all four DNA nucleobases have been prepared and oligomerized by solid-phase synthesis. Four DNA decamers containing 1-10 of these 'PPNA' monomers were prepared and evaluated by Tm measurements (medium salt) for binding to their DNA and RNA complements. One central modification reduced the binding strongly (delta Tm = -10 degrees C), but contiguous PPNA monomers gave smaller effects, and the all-PPNA decamer bound to RNA with a delta Tm of -1.2 degrees C per modification. Thus PPNA oligomers are inferior DNA and RNA binders compared to the closely related and strongly binding PNA oligomers.
Kehler
J
J
Department of Chemistry, H. C. Orsted Institute, University of Copenhagen, Denmark.
Henriksen
U
U
Vejbjerg
H
H
Dahl
O
O
D004247:DNA / Q000138:chemical synthesis* / Q000378:metabolism; D009693:Nucleic Acid Hybridization; D063065:Organophosphonates / Q000138:chemical synthesis* / Q000378:metabolism*; D013237:Stereoisomerism
D063065:Organophosphonates; D004247:DNA