TY - JOUR
T1 - Synthesis of p-amino-WNA derivatives to enhance the stability of the anti-parallel triplex
AU - Taniguchi, Yosuke
AU - Togo, Mieko
AU - Aoki, Eriko
AU - Uchida, Yuko
AU - Sasaki, Shigeki
N1 - Funding Information:
S.S. and Y.T. are grateful for the support by a Grant-in-Aid for Scientific Research (A) and Young Scientists (Start-up) from the Japan Society for the Promotion of Science (JSPS) and CREST from Japan Science and Technology Agency (JST).
PY - 2008/7/21
Y1 - 2008/7/21
N2 - We have previously developed W-shaped nucleoside analogs (WNAs) having a nucleobase and an aromatic ring for the formation of the unnatural triplex DNA. Modification of an aromatic ring of WNA is highly effective regarding the stability of the triplex DNA. In this study, we designed new WNA analogs having the p-aminobenzene as an aromatic ring, which were synthesized via the Curtius-Yamada rearrangement. Based on the evaluation of the triplex formation with p-amino-WNA-TFO, it has been shown that the amino group may produce a non-selective interaction with the phosphate backbone of the target duplexes. These results indicate that the amino modification is useful to overcome the sequence-dependence of the TFO containing WNA analogs.
AB - We have previously developed W-shaped nucleoside analogs (WNAs) having a nucleobase and an aromatic ring for the formation of the unnatural triplex DNA. Modification of an aromatic ring of WNA is highly effective regarding the stability of the triplex DNA. In this study, we designed new WNA analogs having the p-aminobenzene as an aromatic ring, which were synthesized via the Curtius-Yamada rearrangement. Based on the evaluation of the triplex formation with p-amino-WNA-TFO, it has been shown that the amino group may produce a non-selective interaction with the phosphate backbone of the target duplexes. These results indicate that the amino modification is useful to overcome the sequence-dependence of the TFO containing WNA analogs.
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U2 - 10.1016/j.tet.2008.05.096
DO - 10.1016/j.tet.2008.05.096
M3 - Article
AN - SCOPUS:45449110946
SN - 0040-4020
VL - 64
SP - 7164
EP - 7170
JO - Tetrahedron
JF - Tetrahedron
IS - 30-31
ER -