Peptide nucleic acid (PNA) with a chiral backbone based on alanine

PNA: Synthetic Polyamide Nucleic Acids with Unusual Binding Properties

“…The amino acid derivatives that constitute the backbone are assembled through reductive amination of Boc-alaninal with glycine methyl ester [28] (H) or of Boc-glycinal with amino acid esters [46,47] (I), followed by coupling of the nucleobase acetic acid derivatives to give the desired monomeric building blocks.…”

“…Figure 12. Monomers H, [28] [46,47] , J (based on ornithine), [48,49] K, L (based on proline), [50±53] M (based on diaminocyclohexane) [54,55] and N (based on 2-aminopropan-1,3-diol) [56] with chiral backbones and monomers based on a Z-olefinic structure (O). [57] 3.…”

Insights on chiral, backbone modified peptide nucleic acids: Properties and biological activity

“…Conversely, the use of monomers containing D-alanine produced PNAs able to bind to cDNAs with similar stability. 84 Hence, PNA containing the D-form of 1 (Fig. 7) hybridized to complementary DNA with higher affinity than PNA containing the L-form of 1 (Fig.…”

“…83 Nielsen et al first reported a monomer in which the glycine moiety was replaced by alanine. 84 Both the D and L enantiomers were synthesized and inserted into different oligomers. The thermal stability of the PNA-DNA duplexes containing the L-form alanine showed reduced stability compared to PNA-DNA duplex containing glycine.…”

“…7). 84 Lysine, arginine and serine were used in place of glycine to produce relevant PNA monomers bringing an a-amino functionality on the backbone. 85 The lysine containing monomer possesses a positive charge which is known to be beneficial in the formation of PNA-DNA duplex.…”