Synthesis and Properties of 5-Cyano-Substituted Nucleoside Analog with a Donor-Donor-Acceptor Hydrogen-Bonding Pattern

被引：12

作者：

Kim, Hyo-Joong ^{[1
,2
]}

Chen, Fei ^{[1
,2
,3
]}

Benner, Steven A. ^{[1
,2
]}

机构：

[1] Fdn Appl Mol Evolut FfAME, Gainesville, FL 32601 USA

[2] Westheimer Inst Sci & Technol TWIST, Gainesville, FL 32601 USA

[3] Chinese Acad Sci, Beijing Inst Genom, CAS Key Lab Genome Sci & Informat, Beijing, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2012年 / 77卷 / 07期

关键词：

UNNATURAL BASE-PAIR; DNA; OLIGONUCLEOTIDES; RECOGNITION;

D O I：

10.1021/jo300230z

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

6-Aminopyridin-2-ones form Watson-Crick pairs with complementary purine analogues to add a third nucleobase pair to DNA and RNA, if an electron-withdrawing group at position 5 slows oxidation and epimerization. In previous work with a nucleoside analogue trivially named dZ, the electron withdrawing unit was a nitro group. Here, we describe an analogue of dZ (cyanc-dZ) having a cyano group instead of a nitro group, including its synthesis, pK(a), rates of acid-catalyzed epimerization, and enzymatic incorporation.

引用

页码：3664 / 3669

页数：6

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