Synthesis of α-PNA containing a functionalized triazine as nucleobase analogue

The design of artificial structures such as Peptide Nucleic Acids (PNAs) capable of recognizing nucleic acids has attracted much attention. We report herein the design of l-homoserine derivatives bearing diaminotriazine groups as artificial nucleobase capable of pairing to thymine. We set up an original six-step synthetic route (45% overall yield) that enables the functionalization of the nucleobase analogue. Furthermore, we show that these modified amino acids can be incorporated, by solid-phase peptide synthesis, into alternate and homopolymer α-PNAs, thereby giving access to α-PNAs in which the nucleobase analogue bears functional groups that may prove useful for the multi-point recognition of nucleic acids.