ol027026a_si_001.pdf (15.09 kB)
High-Affinity Peptide Nucleic Acid Oligomers Containing Tricyclic Cytosine Analogues†
journal contribution
posted on 2002-11-15, 00:00 authored by Kallanthottathil G. Rajeev, Martin A. Maier, Elena A. Lesnik, Muthiah ManoharanPeptide nucleic acid (PNA) monomers containing the tricyclic cytosine analogues phenoxazine, 9-(2-aminoethoxy)phenoxazine (G-clamp), and
9-(3-aminopropoxy)phenoxazine (propyl-G-clamp) have been synthesized. The modified nucleobases were incorporated into PNA oligomers
using Boc-chemistry for solid-phase synthesis. PNAs containing single G-clamp modifications exhibit significantly enhanced affinity toward
RNA and DNA targets relative to unmodified PNA while maintaining mismatch discrimination. These PNA G-clamp modifications exhibit the
highest increase in affinity toward nucleic acid targets reported so far for PNA modifications.