在脱氧尿苷C5位连接有反应性和稳定基团的寡核苷酸衍生物。

Oligonucleotide derivatives bearing reactive and stabilizing groups attached to C5 of deoxyuridine.

作者信息

Levina A S, Tabatadse D R, Khalimskaya L M, Prichodko T A, Shishkin G V, Alexandrova L A, Zarytova V P

机构信息

Institute of Bioorganic Chemistry, Siberian Division of the Russian Academy of Sciences, Novosibirsk.

出版信息

Bioconjug Chem. 1993 Sep-Oct;4(5):319-25. doi: 10.1021/bc00023a003.

DOI:10.1021/bc00023a003

PMID:8274514

Abstract

Oligonucleotides bearing an aliphatic amino group at the C5-position of deoxyuridine (ULNH2TCCCA, TULNH2CCCA, ULNH2CCACTT, where L = -CH2-, -CH2OCH2CH2- or -CH2NHCOCH2CH2-) have been synthesized. The photoactive (p-azidotetrafluorobenzamido, 2-nitro-5-azidobenzamido, or p-azidobenzamido), alkylating [4-[N-(2-chloroethyl)-N-methylamino]benzyl], or intercalating [N-(2-hydroxyethyl)phenazinium] groups were attached to the amino linker of oligonucleotides. The Tm values were determined for the duplexes formed by the above oligonucleotide derivatives. The alkylating group does not change the melting temperature of the corresponding duplex. The duplex stability is increased a little in the case of photoactive groups. The influence of the phenazinium residue on the duplex stability strongly depends on its location in the oligonucleotide. The spacer length between the C5 atom of deoxyuridine and the photoactive or phenazinium group was shown to influence the complementary duplex stability.

摘要

已合成在脱氧尿苷的C5位带有脂肪族氨基的寡核苷酸（ULNH2TCCCA、TULNH2CCCA、ULNH2CCACTT，其中L = -CH2-、-CH2OCH2CH2-或-CH2NHCOCH2CH2-）。将光活性基团（对叠氮基四氟苯甲酰胺基、2-硝基-5-叠氮基苯甲酰胺基或对叠氮基苯甲酰胺基）、烷基化基团[4-[N-(2-氯乙基)-N-甲氨基]苄基]或嵌入基团[N-(2-羟乙基)吩嗪鎓]连接到寡核苷酸的氨基连接臂上。测定了由上述寡核苷酸衍生物形成的双链体的解链温度（Tm值）。烷基化基团不会改变相应双链体的解链温度。对于光活性基团，双链体稳定性略有增加。吩嗪鎓残基对双链体稳定性的影响很大程度上取决于其在寡核苷酸中的位置。已表明脱氧尿苷的C5原子与光活性基团或吩嗪鎓基团之间的间隔长度会影响互补双链体的稳定性。