posted on 2001-01-10, 00:00authored byAsk Püschl, Thomas Boesen, Guido Zuccarello, Otto Dahl, Stefan Pitsch, Peter E. Nielsen
To preorganize PNA for duplex formation, a new cyclic pyrrolidinone PNA analogue has been
designed. In this analogue the aminoethylglycine backbone and the methylenecarbonyl linker are
connected, introducing two chiral centers compared to PNA. The four stereoisomers of the adenine
analogue were synthesized, and the hybridization properties of PNA decamers containing one
analogue were measured against complementary DNA, RNA, and PNA strands. The (3S,5R) isomer
was shown to have the highest affinity toward RNA, and to recognize RNA and PNA better than
DNA. The (3S,5R ) isomer was used to prepare a fully modified decamer which bound to rU10 with
only a small decrease in Tm (ΔTm/mod = 1 °C) relative to aminoethylglycine PNA.