| Abstract
| - To preorganize PNA for duplex formation, a new cyclic pyrrolidinone PNA analogue has beendesigned. In this analogue the aminoethylglycine backbone and the methylenecarbonyl linker areconnected, introducing two chiral centers compared to PNA. The four stereoisomers of the adenineanalogue were synthesized, and the hybridization properties of PNA decamers containing oneanalogue were measured against complementary DNA, RNA, and PNA strands. The (3S,5R) isomerwas shown to have the highest affinity toward RNA, and to recognize RNA and PNA better thanDNA. The (3S,5R ) isomer was used to prepare a fully modified decamer which bound to rU10 withonly a small decrease in Tm (ΔTm/mod = 1 °C) relative to aminoethylglycine PNA.
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