Cationic guanine: positively charged nucleobase with improved DNA affinity inhibits self-duplex formation

Abstract

Oligonucleotides represent powerful DNA-recognition tools, but the formation of undesirable “self-duplexes” becomes more probable with increasing DNA affinity. Herein, we have developed a modified nucleobase with “self-avoiding” properties. Facile methylation of guanine yields a cationic N⁷-methylguanine, which suppresses the formation of self-duplexes whilst improving DNA affinity through electrostatic interaction.