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Paper | Special issue | Vol 88, No. 1, 2014, pp.377-386
Published online, 19th July, 2013
DOI: 10.3987/COM-13-S(S)33
The Ability of 1-Aryltriazole-Containing Nucleobases to Recognize a TA Base Pair in Triplex DNA

Yoshiyuki Hari,* Motoi Nakahara, Shin Ijitsu, and Satoshi Obika*

*Graduate School of Pharmaceutical Science, Osaka University, 1-6 Yamadaoka, Suita, Osaka 560-0871, Japan

Abstract

Phosphoramidites bearing propargyl and (N-propargylcarbamoyl)methyl groups at the C1-position of deoxyribose were synthesized and introduced into oligonucleotides by using an automated DNA synthesizer. Copper-catalyzed alkyne-azide 1,3-dipolar cycloaddition of the oligonucleotides with various aryl azides led to triplex-forming oligonucleotides (TFOs) possessing the corresponding aryltriazole-containing nucleobases. The triplex-forming ability of TFOs with double-stranded DNA (dsDNA) was evaluated through UV-melting experiments, and it was demonstrated that m-hydroxy or m-ureido derivatives in the (1-aryltriazol-4-yl)methyl nucleobases likely interacted with a TA base pair in dsDNA.