A 2-AMINO-6-METHYLPYRIDIN-5-YL NUCLEOBASE FOR GC BASE PAIR RECOGNITION IN THE PARALLEL TRIPLEX DNA

作者：Nakahara Motoi^*; Hari Yoshiyuki; Obika Satoshi

来源：Heterocycles, 2012, 86(2): 1135-1146.

DOI：10.3987/COM-12-S(N)68

• 2-Aminopyridine
• DNA Recognition
• Nucleobase
• Oligonucleotide
• Triplex DNA

DNA triple helices containing consecutive C+H center dot GC triplets are unstable at neutral pH because protonations of cytosines into the third strand are necessary. Previously, a 2-aminopyridin-5-yl nucleobase (P) was developed and has been widely used as a substitute for the cytosine nucleobase. In this work, we designed a 2-amino-6-methylpyridin-5-yl nucleobase (P-Me), which could preferentially adopt an anti-orientation by the 6-methyl group. This might lead to formation of a stable base triplet with a GC base pair compared to P. We also synthesized 15-mer triplex-forming oligonucleotides (TFOs) containing P-Me by the standard solid-phase method and evaluated the triplex stability of the TFOs at neutral pH by UV melting experiments.

• 出版日期2012-12-31