Synthesis and Evaluation of MGB Polyamide-Oligonucleotide Conjugates as Gene Expression Control Compounds

Scheme 6

Synthesis of pyrrole-γ-imidazole polyamide derivatives. Reagents and conditions: i 1 M NaOH aq./EtOH/pyridine, rt; Dowex 50 WX8 (H⁺-form). ii H₂N(CH₂)₃CO₂Et, EDCI, DMAP, CH₂Cl₂, rt, 32 (82%). iii AcCl, CH₃OH, rt–40°C. iv 26, EDCI, DMAP, CH₂Cl₂, rt, 33 (70%). v EDCI, DMAP, CH₂Cl₂, rt, 34 (57%). vi 8, 9 or 10, EDCI, DMAP, CH₂Cl₂, rt, 35 (55%); 36 (53%); 37 (27%).