Ac. Vanderlaan et al., OPTIMIZATION OF THE BINDING-PROPERTIES OF PNA-(5')-DNA CHIMERAE, Bioorganic & medicinal chemistry letters, 8(6), 1998, pp. 663-668
The synthesis and evaluation of PNA-(5')-DNA chimerae containing eithe
r a 5'-amide (i.e. la), a 5'-phosphodiester (i.e. 1b) or 5'-phosphonat
e linkages (i.e. 1c,d) at the junction site are described. The 5'-link
ages could be installed using either 5'-amino-5'-deoxythymidine phosph
oramidite 2, O-[2-(2-aminoethyl)-(thymin-1-ylacetyl)amino]ethyl phosph
oramidite 3, N-(2-aminoethyl)-N-(thymin-1-ylacetyl)aminomethyl phospho
nate 4 or N-(2-aminoethyl)-N-(allyloxycarbonyl)ami phosphonate 5 as bu
ilding blocks, respectively. It is shown that PNA-(5')-DNA of type la-
e have a higher binding affinity with complementary RNA than native DN
A, and that the antisense activity is mainly due to RNase H. (C) 1998
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